JP7682464B2 - Method for producing hydroxyalkylcarboxamide compound and hydroxyalkylcarboxamide compound - Google Patents

Description

The present invention relates to a method for producing a hydroxyalkylcarboxamide compound having a blocked isocyanato group and a hydroxy group, and to the hydroxyalkylcarboxamide compound.

Among carbamic acid esters, those generally called blocked isocyanates are synthesized by reacting isocyanates with a blocking agent for the isocyanato group (-NCO). Conventionally, compounds that add active hydrogen to the isocyanato group, such as pyrazoles and ketoximes, have been used as blocking agents for the isocyanato group. When carbamic acid esters obtained from pyrazoles or ketoximes are heated, the blocking agent is dissociated and the isocyanato group is regenerated, becoming isocyanates. Such carbamic acid esters are widely used as compounds having blocked isocyanato groups in which the isocyanato group is protected with a blocking agent.

Compounds having a blocked isocyanato group are required to be versatile and usable as materials for a variety of compounds, and examples of such compounds include compounds having a blocked isocyanato group and a hydroxyl group in the molecule.
A compound having a blocked isocyanato group and a hydroxy group can carry out various reactions using the hydroxy group, and can react with a variety of compounds. Furthermore, a compound having a blocked isocyanato group and a hydroxy group can self-polymerize because it can form a urethane bond (-NH-CO-O-) when the blocking agent is dissociated.

Methods for synthesizing a compound having a blocked isocyanato group and a hydroxyl group include, for example, the methods described in Patent Documents 1 and 2. Patent Documents 1 and 2 describe methods for synthesizing a compound having a blocked isocyanato group and a hydroxyl group using phosgene or a chloroformic acid compound as a raw material.

DE 10 2013 021 933 A1 DE 1 618 361 A1

However, in the manufacturing methods of compounds having blocked isocyanato groups and hydroxyl groups described in Patent Document 1 and Patent Document 2, phosgene or chloroformic acid compounds are used as raw materials. Phosgene and chloroformic acid are difficult to handle because they are toxic substances. In addition, phosgene and chloroformic acid compounds are compounds that contain halogens. If halogen-containing compounds remain as impurities in compounds used in electronic components, they may cause problems in the electronic components. For this reason, it is desirable not to use halogen-containing compounds as raw materials for compounds used in electronic components.

As a method for synthesizing a compound having a blocked isocyanato group and a hydroxyl group without using a compound containing a halogen, it is possible to synthesize an isocyanate having a hydroxyl group and then protect the isocyanato group with a blocking agent.

However, isocyanato groups are highly reactive with hydroxyl groups. For this reason, it is difficult to have both isocyanato groups and hydroxyl groups present in a compound. In addition, the reactivity of isocyanato groups with hydroxyl groups is higher than the reactivity of isocyanato groups with active hydrogen in a blocking agent. For these reasons, it is difficult to synthesize a compound having a blocked isocyanato group and a hydroxyl group by using a method in which an isocyanate having a hydroxyl group is synthesized and the isocyanate group is protected with a blocking agent.

Therefore, with conventional techniques, it has been difficult to synthesize a compound having a blocked isocyanato group and a hydroxy group without using a compound containing a halogen.
There is also a need for a novel hydroxyalkylcarboxamide compound which has a blocked isocyanato group and a hydroxy group and can be produced without using a compound containing a halogen.

The present invention has been made in consideration of the above circumstances, and aims to provide a method for producing a hydroxyalkylcarboxamide compound that synthesizes a hydroxyalkylcarboxamide compound having a blocked isocyanato group and a hydroxy group without using a compound containing a halogen, and a hydroxyalkylcarboxamide compound.

The present inventors have conducted extensive research to solve the above problems.
As a result, the present inventors have found that a hydroxyalkylcarboxamide compound can be obtained without using a compound containing a halogen by reacting a specific carbamic acid ester (and/or a cyclized product thereof) with a specific blocking agent in the presence of a solvent, and have thus arrived at the present invention.
That is, the present invention relates to the following.

[1] A method for producing a hydroxyalkylcarboxamide compound, comprising a first step of reacting one or both of a carbamic acid ester represented by the following general formula (3) and a cyclized product of the carbamic acid ester represented by the following general formula (4) with a blocking agent containing a pyrazole ring represented by the following general formula (5) in the presence of a solvent to synthesize a compound represented by the following general formula (6).

（式（３）において、Ｒ^１は－ＣＨ_３、－ＣＨ_２－ＣＨ_３を示す。式（３）、式（４）および式（６）において、Ｒ^２は炭素原子数２～６の直鎖状アルキレン基または炭素原子数４～６のシクロアルキレン基を示す。式（５）および式（６）において、Ｒ^３およびＲ^５はそれぞれ－Ｈ、－ＣＨ_３または－ＣＨ_２－ＣＨ_３のいずれかを示し、Ｒ^４は－Ｈを示す。式（５）において、Ｘは水素原子、アルカリ金属原子のいずれかを示す。）

(In formula (3), R ¹ represents -CH ₃ or -CH ₂ -CH _3. In formulas (3), (4) and (6), R ² represents a linear alkylene group having 2 to 6 carbon atoms or a cycloalkylene group having 4 to 6 carbon atoms. In formulas (5) and (6), R ³ and R ⁵ each represent -H, -CH ₃ or -CH ₂ -CH ₃ , and R ⁴ represents -H. In formula (5), X represents a hydrogen atom or an alkali metal atom.)

[2] Before the first step,
A method for producing a hydroxyalkylcarboxamide compound according to [1], characterized in that a second step is carried out in which a dialkyl carbonate represented by the following general formula (1) is reacted with a compound having an amino group and a hydroxy group represented by the following general formula (2) to synthesize either or both of a carbamic acid ester represented by the following general formula (3) and a cyclized product of a carbamic acid ester represented by the following general formula (4):

（式（１）および式（３）において、Ｒ^１は－ＣＨ_３、－ＣＨ_２－ＣＨ_３を示す。式（１）中の２つのＲ^１は同じである。式（２）～式（４）において、Ｒ^２は炭素原子数２～６の直鎖状アルキレン基または炭素原子数４～６のシクロアルキレン基を示す。）

(In formula (1) and formula (3), R ¹ represents -CH ₃ or -CH ₂ -CH _3. The two R ^1s in formula (1) are the same. In formulas (2) to (4), R ² represents a linear alkylene group having 2 to 6 carbon atoms or a cycloalkylene group having 4 to 6 carbon atoms.)

[3] A method for producing a hydroxyalkylcarboxamide ^compound according to [1] or [2], characterized in that in formula (3), R ¹ represents -CH ₃ , in formulas (3), (4) and (6), R ² represents -CH ₂ -CH ₂ -, and in formulas (5) and ( ⁶ ), R 3 and R ⁵ represent -CH ₃ , and R 4 represents -H.

[4] A method for producing a hydroxyalkylcarboxamide compound according to any one of [1] to [3], characterized in that in the first step, either one or both of the carbamic acid ester and the cyclized product are reacted with the blocking agent in the presence of an activating agent consisting of a base compound.

[5] The method for producing a hydroxyalkylcarboxamide compound according to [4], wherein the activator is at least one selected from the group consisting of alkali metal hydrides, alkaline earth metal hydrides, primary to tertiary alkoxides, alkali metal hydroxides, and alkali metal phosphates.
[6] The method for producing a hydroxyalkylcarboxamide compound according to [4], wherein the activator is any one selected from the group consisting of lithium methoxide, sodium methoxide, and sodium tert-butoxide.

[7] The method for producing a hydroxyalkylcarboxamide compound according to any one of [1] to [6], wherein in the first step, either one or both of the carbamic acid ester and the cyclized product are reacted with the blocking agent in an amide solvent.
[8] The method for producing a hydroxyalkylcarboxamide compound according to [7], wherein the amide solvent is N,N-dimethylformamide.

[9] A hydroxyalkylcarboxamide compound represented by the following general formula (60):

（式（６０）において、Ｒ^２０は－ＣＨ_２－ＣＨ_２－ＣＨ_２－を示す。Ｒ^３０およびＲ^５０はそれぞれ－Ｈ、－ＣＨ_３または－ＣＨ_２－ＣＨ_３のいずれかを示し、Ｒ^４０は－Ｈを示す。）

(In formula (60), R ²⁰ represents -CH ₂ -CH ₂ -CH ₂ -. ^{R 30} and R ⁵⁰ each represent -H, -CH ₃ or -CH ₂ -CH ₃ , and R ⁴⁰ represents -H.)

According to the method for producing a hydroxyalkylcarboxamide compound of the present invention, a hydroxyalkylcarboxamide compound having a blocked isocyanato group and a hydroxy group can be produced without using a compound containing a halogen.
According to the present invention, a novel hydroxyalkylcarboxamide compound having a blocked isocyanato group and a hydroxy group can be provided.

FIG. 1 is a ¹ H-NMR measurement chart of Example 1. FIG. 2 is a ¹³ C-NMR measurement chart of Example 1. FIG. 3 is a ¹ H-NMR measurement chart of Example 28. FIG. 4 is a ¹³ C-NMR measurement chart of Example 28. FIG. 5 is a ¹ H-NMR measurement chart of Example 29. FIG. 6 is a ¹³ C-NMR measurement chart of Example 29.

The method for producing the compound of the present invention will be described in detail below. Note that the present invention is not limited to the embodiments shown below.

<Method of producing the compound>
The method for producing a hydroxyalkylcarboxamide compound of the present embodiment includes a carbamate synthesis step (corresponding to the "second step" in the claims) and a carboxamide compound synthesis step (corresponding to the "first step" in the claims).

The carbamic acid ester synthesis process can be, for example, the process shown below. First, a dialkyl carbonate represented by the following general formula (1) is reacted with a compound having an amino group and a hydroxyl group represented by the following general formula (2). This synthesizes either or both of a carbamic acid ester represented by the following general formula (3) and a cyclized product of the carbamic acid ester represented by the following general formula (4).

（式（１）および式（３）において、Ｒ^１は－ＣＨ_３、－ＣＨ_２－ＣＨ_３を示す。式（１）中の２つのＲ^１は同じである。式（２）～式（４）において、Ｒ^２は炭素原子数２～６の直鎖状アルキレン基または炭素原子数４～６のシクロアルキレン基を示す。）

(In formula (1) and formula (3), R ¹ represents -CH ₃ or -CH ₂ -CH _3. The two R ^1s in formula (1) are the same. In formulas (2) to (4), R ² represents a linear alkylene group having 2 to 6 carbon atoms or a cycloalkylene group having 4 to 6 carbon atoms.)

In the carboxamide compound synthesis process, either or both of the carbamate ester represented by formula (3) and the cyclized product represented by formula (4) are reacted with a blocking agent containing a pyrazole ring represented by the following general formula (5) in the presence of a solvent. This synthesizes a hydroxyalkylcarboxamide compound represented by the following general formula (6).

（式（３）において、Ｒ^１は－ＣＨ_３、－ＣＨ_２－ＣＨ_３を示す。式（３）、式（４）および式（６）において、Ｒ^２は炭素原子数２～６の直鎖状アルキレン基または炭素原子数４～６のシクロアルキレン基を示す。式（５）および式（６）において、Ｒ^３およびＲ^５はそれぞれ－Ｈ、－ＣＨ_３または－ＣＨ_２－ＣＨ_３のいずれかを示し、Ｒ^４は－Ｈを示す。式（５）において、Ｘは水素原子、アルカリ金属原子のいずれかを示す。）

(In formula (3), R ¹ represents -CH ₃ or -CH ₂ -CH _3. In formulas (3), (4) and (6), R ² represents a linear alkylene group having 2 to 6 carbon atoms or a cycloalkylene group having 4 to 6 carbon atoms. In formulas (5) and (6), R ³ and R ⁵ each represent -H, -CH ₃ or -CH ₂ -CH ₃ , and R ⁴ represents -H. In formula (5), X represents a hydrogen atom or an alkali metal atom.)

(Carbamic acid ester synthesis process)
In the carbamic acid ester synthesis step, the dialkyl carbonate represented by formula (1) used as a raw material is dimethyl carbonate in which both of the two R ¹ in formula (1) are -CH ₃ , or diethyl carbonate in which both of the two R ¹ in formula (1) are -CH ₂ -CH ₃ , and is preferably dimethyl carbonate. When the dialkyl carbonate represented by formula (1) is dimethyl carbonate, the product eliminated from the raw material during the synthesis of the hydroxyalkylcarboxamide compound represented by general formula (6) is methanol. Methanol is a compound with a low boiling point, and therefore is easily separated from the reaction product, and is therefore preferred.

In the carbamic acid ester synthesis step, the compound having an amino group and a hydroxy group and represented by formula (2) used as a raw material is one in which R ² in formula (2) is a linear alkylene group having 2 to 6 carbon atoms or a cycloalkylene group having 4 to 6 carbon atoms. As the compound having an amino group and a hydroxy group and represented by formula (2), it is preferable to use ethanolamine in which R ² is -CH ₂ -CH ₂ -, or 3-amino-1-propanol in which R ² is -CH ₂ -CH ₂ -CH ₂ -, because a hydroxyalkylcarboxamide compound represented by formula (6) is highly versatile. In addition, when R ² is a cycloalkylene group having 4 to 6 carbon atoms, it is preferably a cyclohexene group.

In the carbamate synthesis step, the conditions for reacting the dialkyl carbonate represented by formula (1) with the compound having an amino group and a hydroxy group represented by formula (2) are not particularly limited and can be appropriately determined depending on the types of the dialkyl carbonate represented by formula (1) and the compound represented by formula (2).
For example, when the dialkyl carbonate represented by formula (1) is dimethyl carbonate and the compound represented by formula (2) is ethanolamine, the reaction is preferably carried out in a closed vessel in the absence of a solvent.
In this case, the reaction temperature is preferably in the range of 25° C. to 150° C., more preferably in the range of 35° C. to 120° C., even more preferably in the range of 50° C. to 100° C., more preferably in the range of 60 to 95° C., and particularly preferably in the range of 70° C. to 90° C. The reaction time is preferably in the range of 0.5 hours to 24 hours, more preferably in the range of 1 hour to 12 hours, and even more preferably in the range of 2 hours to 6 hours.

The reaction for synthesizing either or both of the carbamic acid ester represented by formula (3) and the cyclized product represented by formula (4) in the carbamic acid ester synthesis step may be carried out in the presence of a catalyst to promote the reaction.
Examples of the catalyst that can be used include lithium hydride, sodium hydride, potassium hydride, lithium methoxide, sodium methoxide, potassium methoxide, calcium methoxide, lithium tert-butoxide, sodium tert-butoxide, potassium tert-butoxide, triethylamine, diazabicycloundecene, sodium hydroxide, potassium phosphate, sodium phosphate, lithium phosphate, etc. Among these, the use of sodium methoxide and sodium tert-butoxide is particularly preferred in terms of reaction yield.
The content of the catalyst may be, for example, 0.01 to 0.1 molar equivalents relative to the compound represented by the formula (2).

In the carbamic acid ester synthesis step, either or both of the carbamic acid ester represented by formula (3) and the cyclized product of the carbamic acid ester represented by formula (4) are synthesized. In the carbamic acid ester synthesis step, only either the carbamic acid ester represented by formula (3) and the cyclized product of the carbamic acid ester represented by formula (4) may be selectively synthesized, or a mixture containing these in any ratio may be synthesized.

(Carboxamide compound synthesis process)
The blocking agent containing a pyrazole ring and represented by formula (5) used in the carboxamide compound synthesis step is one in which R ³ and R ⁵ in formula (5) are each -H, -CH ₃ or -CH ₂ -CH ₃ , R ⁴ is -H, and X is a hydrogen atom or an alkali metal atom.
As the blocking agent containing a pyrazole ring represented by formula (5), one in which R ³ and R ⁵ are -CH ₃ is preferred. When R ³ and R ⁵ are -CH ₃ , the blocking agent is easily dissociated by heating the produced hydroxyalkylcarboxamide compound represented by formula (6), and the isocyanato group is regenerated, making the compound highly versatile.

X in formula (5) may be a hydrogen atom or an alkali metal atom. When X is an alkali metal atom, the compound represented by formula (6) can be obtained in high yield without using an activator. When X is an alkali metal atom, examples of the alkali metal include lithium, sodium, and potassium, and sodium is preferred because it is inexpensive and easily available.

The ratio of either or both of the carbamic acid ester represented by formula (3) and the cyclized product of the carbamic acid ester represented by formula (4) to the blocking agent represented by formula (5) used in the carboxamide compound synthesis step is preferably in the range of 1:1 to 1:10 in molar ratio (formula (3) (and/or formula (4)):blocking agent), and more preferably in the range of 1:1 to 1:5, in order to obtain the hydroxyalkylcarboxamide compound represented by formula (6) in high yield.

In the carboxamide compound synthesis step, either one or both of the carbamic acid ester represented by formula (3) and the cyclized product of the carbamic acid ester represented by formula (4) are reacted with a blocking agent in the presence of a solvent. The solvent used in the carboxamide compound synthesis step is preferably a polar solvent having a high boiling point.
Specifically, examples of the solvent that can be used include N,N-dimethylacetamide (DMAc), N,N-dimethylformamide (DMF), N-methyl-2-pyrrolidone (NMP), acetonitrile, formamide, dimethylsulfoxide (DMSO), hexamethylphosphoric triamide, anisole, dimethoxyethane, diethylene glycol dimethyl ether, etc. Among these, it is preferable to use an amide solvent such as N,N-dimethylacetamide, N,N-dimethylformamide, or N-methyl-2-pyrrolidone, since the compound represented by formula (6) can be obtained in a high yield, and it is particularly preferable to use N,N-dimethylformamide.

The total content of the carbamic acid ester represented by formula (3) and/or the cyclized product of the carbamic acid ester represented by formula (4) and the blocking agent containing a pyrazole ring represented by formula (5) contained in the solvent is preferably in the range of 0.2 mol/L to 4.0 mol/L, and more preferably in the range of 0.5 mol/L to 1.5 mol/L, in order to obtain the compound represented by formula (6) in a high yield.

In the carboxamide compound synthesis process, the conditions for synthesizing the compound represented by formula (6) by reacting one or both of the carbamic acid ester represented by formula (3) and the cyclized product of the carbamic acid ester represented by formula (4) with a blocking agent containing a pyrazole ring represented by formula (5) can be appropriately determined depending on the type of the target compound represented by formula (6), the type of solvent used, etc., and are not particularly limited.

For example, when the hydroxyalkylcarboxamide compound represented by formula (6) has R ² as —CH ₂ —CH ₂ —, R ³ and R ⁵ as —CH ₃ , and R ⁴ as —H, the following reaction temperature and reaction time are preferred.
That is, the reaction temperature is preferably in the range of 100° C. to 200° C., more preferably in the range of 130° C. to 160° C., so as to suppress the production of the by-product 2-oxazolidone and to obtain the compound represented by formula (6) in a high yield.

The reaction time in the carboxamide compound synthesis process is preferably in the range of 3 to 20 hours, and more preferably in the range of 4 to 10 hours, in order to obtain the compound represented by formula (6) in high yield. If the reaction time is 3 to 20 hours, the production of oligomers and/or polymers as by-products can be suppressed, and the productivity is good.

In order to promote the above reaction, the reaction in the carboxamide compound synthesis step is preferably carried out in the presence of an activator consisting of a base compound. As the activator consisting of a base compound, one or more selected from alkali metal hydrides, alkaline earth metal hydrides, primary to tertiary alkoxides, alkali metal hydroxides, alkali metal phosphates, organic bases, etc. can be used. As the activator, an acid catalyst such as trifluoromethanesulfonic acid (TfOH) can also be used.

Specifically, lithium hydride, sodium hydride, potassium hydride, lithium methoxide, sodium methoxide, potassium methoxide, calcium methoxide, lithium tert-butoxide, sodium tert-butoxide, potassium tert-butoxide, triethylamine, diazabicycloundecene, sodium hydroxide, potassium phosphate, sodium phosphate, lithium phosphate, etc. can be used as the activator. Among these, it is preferable to use any one selected from lithium methoxide, sodium methoxide, sodium tert-butoxide, and potassium phosphate as the activator, since the compound represented by formula (6) can be obtained in high yield. In particular, it is preferable to use sodium tert-butoxide, since the compound represented by formula (6) can be obtained in high yield and is easily available.

The amount of activator used in the carboxamide compound synthesis process can be appropriately changed depending on the type of carbamic acid ester represented by formula (3) and/or the cyclized product of the carbamic acid ester represented by formula (4) and the type of blocking agent containing a pyrazole ring represented by formula (5). For example, when the blocking agent containing a pyrazole ring represented by formula (5) is 3,5-dimethylpyrazole, it is preferable to use 1 to 5 equivalents of activator per equivalent of blocking agent, and more preferably 1 to 2 equivalents. When the amount of activator used per equivalent of blocking agent is 1 equivalent or more, the reaction promotion effect by using the activator becomes significant. In addition, when the amount of activator used per equivalent of blocking agent is 5 equivalents or less, it is possible to prevent the solvent from being easily decomposed due to the large amount of activator used, depending on the type of solvent used (e.g., N,N-dimethylformamide (DMF)).

In the manufacturing method of this embodiment, the carbamic acid ester synthesis step is preferably a step of reacting dimethyl carbonate represented by the following formula (11) with ethanolamine represented by the following formula (12). This may synthesize a carbamic acid ester represented by the following formula (13), or may synthesize a cyclized form of a carbamic acid ester represented by the following formula (14). The carboxamide compound synthesis step may also be carried out even if both the compounds represented by formula (13) and formula (14) are present. Therefore, if there is no particular need to synthesize only one of them in the carbamic acid ester synthesis step, both the compounds represented by formula (13) and formula (14) may be synthesized simultaneously.

When the carbamic acid ester represented by formula (13) is synthesized in preference to the cyclized product of the carbamic acid ester represented by formula (14), for example, the dialkyl carbonate represented by formula (11) is supplied in an excess of 1.1 equivalents or more relative to the ethanolamine represented by formula (12), and reacted in a closed system at 50 to 150°C for 1 to 10 hours so that the alkanol (methanol) does not escape from the system. Thereafter, the heat source is removed, and the excess dialkyl carbonate is removed under a reduced pressure atmosphere. The excess carbonate may be removed under a reduced pressure atmosphere during the period from the reaction temperature to room temperature (for example, during the period until the temperature is cooled to 100°C), or the excess carbonate may be removed under a reduced pressure atmosphere after the temperature is cooled to around room temperature.
In addition, when almost selectively synthesizing a cyclized product of the carbamic acid ester represented by formula (14), for example, the following method is used. First, the dialkyl carbonate represented by formula (11) is supplied in an amount of 1.0 to 1.3 times the equivalent of the ethanolamine represented by formula (12), and an activator consisting of the above-mentioned basic compound is added, followed by reaction for 2 to 20 hours at 70 to 150°C in an open system where the generated alkanol is easily distilled off. After the ethanolamine represented by formula (12) is almost completely consumed by the reaction, the remaining dialkyl carbonate represented by formula (11) is distilled off. At the same time, the carbamic acid ester represented by formula (13) contained in the reaction system is heated (80 to 150°C) to promote a dealkanolization reaction (demethanolization reaction) and converted into the cyclized product represented by formula (14).

When both the compounds represented by formula (13) and formula (14) are synthesized simultaneously, for example, the method shown below may be used. First, equimolar amounts of dialkyl carbonate represented by formula (11) and ethanolamine represented by formula (12) are reacted. After the ethanolamine represented by formula (12) is almost completely eliminated by the reaction, the mixture is heated. As a result, a part of the carbamic acid ester represented by formula (13) contained in the reaction system is subjected to a de-methanol reaction and converted into a cyclized product represented by formula (14). At this time, the heating conditions for de-methanolizing the carbamic acid ester represented by formula (13) are appropriately adjusted so that the mixture ratio of the compound represented by formula (13) and the compound represented by formula (14) is within a predetermined range. The higher the heating temperature and the longer the heating time, the more easily the compound represented by formula (13) is converted into a cyclized product represented by formula (14).

In the carbamic acid ester synthesis step, when a compound having an amino group and a hydroxy group represented by general formula (2) in which R ² has 2 carbon atoms is used, the reaction proceeds without using a catalyst, but the reaction rate can be increased by using a catalyst. When a compound having an amino group and a hydroxy group represented by general formula (2) in which R ² has 3 or more carbon atoms is used, a catalyst is used. When a catalyst is used, the mixing ratio of the compound represented by formula (3) and the compound represented by formula (4) can be adjusted by the type and amount of catalyst used. For example, when a strong base such as NaOMe or NaOtBu is used as a catalyst, the compound represented by formula (4) is more likely to be produced than the compound represented by formula (3).
As described above, the compound represented by formula (13) and the compound represented by formula (14) can each be synthesized preferentially.
In this embodiment, when the ethanolamine represented by formula (12) is substantially converted into the compound represented by formula (13) and/or the compound represented by formula (14), the carbamate ester synthesis step is terminated and the process proceeds to the carboxamide compound synthesis step.

In the production method of this embodiment, the carboxamide compound synthesis step is preferably a step of reacting the carbamic acid ester represented by formula (13) produced in the carbamic acid ester synthesis step with 3,5-dimethylpyrazole represented by formula (15) below or a sodium salt of 3,5-dimethylpyrazole represented by formula (25) below, thereby obtaining a compound represented by formula (16) below, as shown in the formula below.
The carboxamide compound synthesis step may be a step of reacting 2-oxazolidinone, which is a cyclized product of the carbamic acid ester represented by formula (14) produced in the carbamic acid ester synthesis step, with 3,5-dimethylpyrazole represented by formula (15) or a sodium salt of 3,5-dimethylpyrazole represented by the following formula (25). In this case as well, the compound represented by formula (16) is obtained as shown in the following formula.

The carboxamide compound synthesis process may be a process in which the carbamic acid ester represented by formula (13) is reacted with 3,5-dimethylpyrazole (and/or the sodium salt of 3,5-dimethylpyrazole) and the cyclized product of the carbamic acid ester represented by formula (14) is reacted with 3,5-dimethylpyrazole (and/or the sodium salt of 3,5-dimethylpyrazole) simultaneously. That is, in the carboxamide compound synthesis process, a mixture of the carbamic acid ester represented by formula (13) and the cyclized product of the carbamic acid ester represented by formula (14) may be used as the raw material. In this case as well, the compound represented by formula (16) is obtained.

According to the method for producing a compound of this embodiment, a compound represented by formula (6) can be produced without using a compound containing a halogen. The compound represented by general formula (6) has a structure in which a nitrogen atom of a blocking agent containing a pyrazole ring represented by general formula (5) is bonded to a carbon atom forming a urethane bond, and a hydroxyl group is bonded to the nitrogen atom forming the urethane bond via an alkyl group. Therefore, the compound represented by general formula (6) can be used as a material for a variety of compounds, as shown below.

That is, the compound represented by the general formula (6) reacts with various compounds by reacting a hydroxy group in the compound with a functional group of the compound having a functional group such as an isocyanato group, an epoxy group, a carboxy group, an ester group, etc. Therefore, the compound represented by the general formula (6) is highly versatile and can be used as a material for various compounds having multiple functional groups.
In addition, the compound represented by the general formula (6) has a blocked isocyanato group and a hydroxyl group, and therefore, as shown in the following formula, the compound represented by the general formula (6) can self-polymerize.

（式（２７）および式（２８）において、Ｒ^２は、式（６）と同じである。）

(In formula (27) and formula (28), ^R2 is the same as in formula (6).)

As shown in the formula above, when the compound represented by general formula (6) is heated, it dissociates the blocking agent represented by general formula (5) and regenerates an isocyanato group (-NCO). The compound represented by general formula (27) having the regenerated isocyanato group reacts with a hydroxy group of another molecule (compound represented by formula (27)) to form a urethane bond (-NH-CO-O-) and polymerize. This forms a polymer represented by general formula (28) (n in the formula is the number of repeats).

The structure of the compound represented by general formula (6) produced by the production method of this embodiment can be confirmed using known techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), infrared spectroscopy (IR), ultraviolet-visible spectroscopy (UV-VIS absorption spectroscopy), and elemental analysis.

<Compound>
The hydroxyalkylcarboxamide compound of this embodiment is represented by the following general formula (60).

（式（６０）において、Ｒ^２０は－ＣＨ_２－ＣＨ_２－ＣＨ_２－を示す。Ｒ^３０およびＲ^５０はそれぞれ－Ｈ、－ＣＨ_３または－ＣＨ_２－ＣＨ_３のいずれかを示し、Ｒ^４０は－Ｈを示す。）

(In formula (60), R ²⁰ represents -CH ₂ -CH ₂ -CH ₂ -. ^{R 30} and R ⁵⁰ each represent -H, -CH ₃ or -CH ₂ -CH ₃ , and R ⁴⁰ represents -H.)

R ³⁰ and R ⁵⁰ in formula (60) are each either -H, -CH ₃ or -CH ₂ -CH ₃ , and are the same as R ³ and R ⁵ in formula (6). R ³⁰ and R ⁵⁰ in formula (60) are preferably -CH ₃ , since this is a highly versatile compound in which the blocking agent is easily dissociated by heating to regenerate the isocyanato group.
The hydroxyalkylcarboxamide compound of the present embodiment has a blocked isocyanato group and a hydroxy group, and is useful as a material for a variety of compounds having polyfunctional groups, and is highly versatile.

[Other examples]
In the production method of this embodiment, a cyclized product of the carbamic acid ester represented by formula (3) and/or the carbamic acid ester represented by formula (4) was synthesized by carrying out a carbamic acid ester synthesis step. However, the method for synthesizing the cyclized product of the carbamic acid ester represented by formula (3) and/or the carbamic acid ester represented by formula (4) is not limited to the above-mentioned method, and any method may be used.

The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples.
"Examples 1 to 11"
The compound represented by formula (16) was synthesized by the method shown below.

(Carbamic acid ester synthesis process)
55 g [0.60 mol] of dimethyl carbonate (manufactured by Tokyo Chemical Industry Co., Ltd.) and 31 g [0.50 mol] of ethanolamine (manufactured by Tokyo Chemical Industry Co., Ltd.) were charged into a sealed container (a glass-stoppered recovery flask (200 mL)) and reacted at 80° C. for 4 hours under solvent-free conditions.
The resulting reaction solution was concentrated under reduced pressure to remove unreacted dimethyl carbonate, and analyzed using gas chromatography (GC2014; manufactured by Shimadzu Corporation). As a result, the product in the reaction solution contained 95% by mass of the carbamic acid ester represented by formula (13) and 5% by mass of the cyclized product of the carbamic acid ester represented by formula (14). The resulting product (55.4 g) was used as it is as a raw material in the carboxamide compound synthesis step without purification.

(Carboxamide compound synthesis process)
In the presence of an activator shown in Table 1 and N,N-dimethylformamide (DMF) (Tokyo Chemical Industry Co., Ltd.) as a solvent, the product (carbamic acid ester) produced in the carbamic acid ester synthesis step was reacted with 3,5-dimethylpyrazole (Tokyo Chemical Industry Co., Ltd.) represented by formula (15) as a blocking agent at the reaction temperature and reaction time shown in Table 1. As a result, a hydroxyalkylcarboxamide compound represented by formula (16) was obtained.
Table 1 shows the types and amounts of carbamic acid esters, blocking agents, activators, and solvents used in the carboxamide compound synthesis process.

As the activators shown in Table 1, the following were used.
MeOLi: Lithium methoxide (Sigma-Aldrich)
MeONa: sodium methoxide (Tokyo Chemical Industry Co., Ltd.)
MeOK: Potassium methoxide (manufactured by SIGMA-ALDRICH)
(MeO) ₂ Ca: Calcium methoxide (manufactured by SIGMA-ALDRICH)
tBuOLi: Lithium tert-butoxide (manufactured by SIGMA-ALDRICH)
tBuONa: sodium tert-butoxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)
tBuOK: potassium tert-butoxide (Tokyo Chemical Industry Co., Ltd.)
Triethylamine: (FUJIFILM Wako Pure Chemical Industries, Ltd.)
Diazabicycloundecene: (Tokyo Chemical Industry Co., Ltd.)
NaOH: Sodium hydroxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)
_K3PO4 : Potassium phosphate (manufactured _by Fujifilm Wako Pure Chemical Industries, Ltd.)

The hydroxyalkylcarboxamide compounds obtained by the production methods of Examples 1 to 11 were analyzed by gas chromatography (GC2014; manufactured by Shimadzu Corporation) using biphenyl as an internal standard substance, and the yields were calculated according to the following formula. The results are shown in Table 1.
Yield (%)=(amount of target compound produced (mol)/amount of carbamic acid ester used (mol))×100

The hydroxyalkylcarboxamide compounds obtained by the production methods of Examples 1 to 11 were each subjected to ¹ H-NMR and ¹³ C-NMR measurements using an NMR (nuclear magnetic resonance) device (Bruker AvanceIII), and the structures were identified from the following results. Figure 1 is a ¹ H-NMR measurement chart for Example 1. Figure 2 is a ¹³ C-NMR measurement chart for Example 1.
As a result, it was confirmed that all of the hydroxyalkylcarboxamide compounds obtained by the production methods of Examples 1 to 11 were the hydroxyalkylcarboxamide compounds represented by formula (16).

¹ H-NMR (600MHz, CDCl ₃ , 300K) δ (ppm): 2.21 (S, 3H, Me), 2.22 (S, 3H, Me), 3.70 (q, J = 5.7, 2H, -CH ₂ -), 4.09 (t, J = 5.6, 2H, -CH ₂ -), 5.81 (S, 1H, CH), 6.54 (S, 1H, OH), 8.17 (S, 1H, NH)
¹³ C{ ¹ H}-NMR (125 MHz, CDCl ₃ , 300 K) δ (ppm): 10.9 (S), 13.2 (S), 37.8 (S), 46.9 (S), 105.5 (S), 140.1 (S), 147.8 (S), 161.4 (S)

As shown in Table 1, in Examples 1 to 11 in which the activators shown in Table 1 were used, the hydroxyalkylcarboxamide compound represented by formula (16) was obtained in all cases.
In particular, in Example 1, in which lithium methoxide was used as an activator, Example 2, in which sodium methoxide was used, Example 6, in which sodium tert-butoxide was used, and Example 11, in which potassium phosphate was used, the compound represented by formula (16) was obtained in a high yield of 40% or more.

"Examples 12 to 22"
(Carbamic acid ester synthesis process)
The carbamate synthesis step was carried out in the same manner as in Example 1.

(Carboxamide compound synthesis process)
In the presence of sodium tert-butoxide as an activating agent, the product (carbamic acid ester) produced in the carbamic acid ester synthesis step was reacted with 3,5-dimethylpyrazole represented by formula (15) as a blocking agent in N,N-dimethylformamide (DMF) as a solvent at the reaction temperature and reaction time shown in Table 2. As a result, a compound represented by formula (16) was obtained.
Table 2 shows the types and amounts of carbamic acid esters, blocking agents, activating agents, and solvents used in the carboxamide compound synthesis process.

The yields of the hydroxyalkylcarboxamide compounds obtained by the manufacturing methods of Examples 12 to 22 were calculated in the same manner as in Example 1. The results are shown in Table 2.

Furthermore, the structures of the hydroxyalkylcarboxamide compounds obtained by the production methods of Examples 12 to 22 were identified in the same manner as in Example 1.
As a result, it was confirmed that all of the hydroxyalkylcarboxamide compounds obtained by the production methods of Examples 12 to 22 were the hydroxyalkylcarboxamide compounds represented by formula (16).

As shown in Table 2, in Examples 12 to 22, the hydroxyalkylcarboxamide compound represented by formula (16) was obtained.
In Example 12, in which the amount of the activator used was 1.5 equivalents relative to 1 equivalent of the blocking agent, a higher yield was obtained as compared with Example 14, in which the amount of the activator used was 2.0 equivalents, and Example 13, in which the amount of the activator used was 1.0 equivalent.

As shown in Table 2, Example 18, in which the amount of solvent used was 4.0 ml, gave a higher yield than Example 12, in which the amount of solvent used was 0.5 ml, Example 16, in which the amount of solvent used was 1.0 ml, and Example 17, in which the amount of solvent used was 2.0 ml.
As shown in Table 2, Example 12, in which the reaction time was 5 hours, gave a higher yield than Example 14, in which the reaction time was 4 hours. Also, Example 17, in which the reaction time was 5 hours, gave a higher yield than Example 19, in which the reaction time was 17 hours.

"Examples 23 to 26"
(Carbamic acid ester synthesis process)
The carbamate synthesis step was carried out in the same manner as in Example 1.

(Carboxamide compound synthesis process)
In the presence of sodium tert-butoxide as an activating agent, the product (carbamic acid ester) produced in the carbamic acid ester synthesis step was reacted with 3,5-dimethylpyrazole represented by formula (15) as a blocking agent in a solvent shown in Table 3 at the reaction temperature and reaction time shown in Table 3. As a result, a compound represented by formula (16) was obtained.
Table 3 shows the types and amounts of carbamic acid esters, blocking agents, activating agents, and solvents used in the carboxamide compound synthesis process.

As the solvents shown in Table 3, the following were used.
DMF: N,N-dimethylformamide (Tokyo Chemical Industry Co., Ltd.)
DMAc: N,N-dimethylacetamide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)
NMP: N-methyl-2-pyrrolidone (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)
Acetonitrile: (FUJIFILM Wako Pure Chemical Industries, Ltd.)
DMSO: Dimethyl sulfoxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)

The yields of the hydroxyalkylcarboxamide compounds obtained by the manufacturing methods of Examples 23 to 26 were calculated in the same manner as in Example 1. The results are shown in Table 3. For comparison, Table 3 also shows the results of Example 13 shown in Table 2.

Furthermore, the structures of the hydroxyalkylcarboxamide compounds obtained by the production methods of Examples 23 to 26 were identified in the same manner as in Example 1.
As a result, it was confirmed that all of the hydroxyalkylcarboxamide compounds obtained by the production methods of Examples 23 to 26 were the hydroxyalkylcarboxamide compounds represented by formula (16).

As shown in Table 3, in Examples 23 to 26, the hydroxyalkylcarboxamide compound represented by formula (16) was obtained.
In particular, in Example 13 in which N,N-dimethylformamide (DMF) was used as the solvent, the compound represented by the formula (16) was obtained in high yield.

"Example 27"
(Carbamic acid ester synthesis process)
The carbamate synthesis step was carried out in the same manner as in Example 1.

(Carboxamide compound synthesis process)
Without using an activating agent, the product (carbamic acid ester) produced in the carbamic acid ester synthesis step was reacted with the sodium salt of 3,5-dimethylpyrazole represented by formula (25) as a blocking agent in a solvent shown in Table 4 at the reaction temperature and reaction time shown in Table 4. As a result, a compound represented by formula (16) was obtained.

The sodium salt of 3,5-dimethylpyrazole used as the blocking agent was synthesized by the following method.
1.9 g (20 mmol) of 3,5-dimethylpyrazole (Tokyo Chemical Industry Co., Ltd.) was dissolved in 2 mL of tetrahydrofuran (THF), and 1.1 g (20 mmol) of sodium methoxide (Tokyo Chemical Industry Co., Ltd.) was added thereto and refluxed for 1 hour. Then, the mixture was concentrated under reduced pressure to obtain 2.3 g of the sodium salt of 3,5-dimethylpyrazole as white crystals.

Table 4 shows the types and amounts of carbamic acid esters, blocking agents, and solvents used in the carboxamide compound synthesis process.

For the hydroxyalkylcarboxamide compound obtained by the production method of Example 27, the yield was calculated in the same manner as in Example 1. The results are shown in Table 4.
In addition, the structure of the hydroxyalkylcarboxamide compound obtained by the production method of Example 27 was identified in the same manner as in Example 1.
As a result, it was confirmed that the hydroxyalkylcarboxamide compound obtained by the production method of Example 27 was the hydroxyalkylcarboxamide compound represented by formula (16).

As shown in Table 4, in Example 27, in which the sodium salt of 3,5-dimethylpyrazole represented by formula (25) was used as the blocking agent, the hydroxyalkylcarboxamide compound represented by formula (16) was obtained in a high yield of 50% or more without using an activating agent.

"Example 28"
A hydroxyalkylcarboxamide compound was produced in the same manner as in Example 21, except that pyrazole (manufactured by Tokyo Chemical Industry Co., Ltd.) was used as the blocking agent instead of 3,5-dimethylpyrazole represented by the formula (15).
Table 4 shows the carbamic acid ester, blocking agent, activating agent, type and amount of solvent used, reaction temperature, and reaction time used in the carboxamide compound synthesis process.
For the hydroxyalkylcarboxamide compound obtained by the production method of Example 28, the yield was calculated in the same manner as in Example 1. The results are shown in Table 4.

The hydroxyalkylcarboxamide compound obtained by the production method of Example 28 was subjected to ¹ H-NMR and ¹³ C-NMR measurements using an NMR (nuclear magnetic resonance) device (Bruker Avance III), and the structure was identified from the following results. Figure 3 is a ¹ H-NMR measurement chart of Example 28. Figure 4 is a ¹³ C-NMR measurement chart of Example 28.
As a result, it was confirmed that the hydroxyalkylcarboxamide compound obtained by the production method of Example 28 was the hydroxyalkylcarboxamide compound represented by formula (16).

¹ H-NMR (600 MHz, CDCl ₃ , 300 K) δ (ppm): 3.78 (dd, J = 11, 5.7 Hz, 2H, -CH ₂ -), 4.32 (t, J = 5.7 Hz, 2H, -CH ₂ -), 6.30 (t, J = 2.1Hz, 1H, CH), 7.42 (d, J = 2.1Hz, 1H, CH), 7.57 (d, J = 2.1Hz, 1H, CH), 8.18 (S, 1H, NH)
¹³ C{ ¹ H}-NMR (125 MHz, CDCl ₃ , 300 K) δ (ppm): 38.3 (S), 50.7 (S), 106.0 (S), 130.5 (S), 139.4 (S), 161.3 (S)

As shown in Table 4, in Example 28, in which pyrazole was used as a blocking agent, the hydroxyalkylcarboxamide compound represented by formula (16) was obtained in a high yield of 60% or more.

"Example 29"
A hydroxyalkylcarboxamide compound was produced in the same manner as in Example 21, except that 3-amino-1-propanol (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of ethanolamine as the compound having an amino group and a hydroxy group.
Table 4 shows the carbamic acid ester, blocking agent, activating agent, type and amount of solvent used, reaction temperature, and reaction time used in the carboxamide compound synthesis process.
For the hydroxyalkylcarboxamide compound obtained by the production method of Example 29, the yield was calculated in the same manner as in Example 1. The results are shown in Table 4.

The hydroxyalkylcarboxamide compound obtained by the production method of Example 29 was subjected to ¹ H-NMR and ¹³ C-NMR measurements using an NMR (nuclear magnetic resonance) device (Bruker Avance III), and the structure was identified from the following results. Figure 5 is a ¹ H-NMR measurement chart of Example 29. Figure 6 is a ¹³ C-NMR measurement chart of Example 29.
As a result, it was confirmed that the hydroxyalkylcarboxamide compound obtained by the production method of Example 29 was a hydroxyalkylcarboxamide compound represented by formula (60) (in formula (60), R ²⁰ represents -CH ₂ -CH ₂ -CH ₂ -, R ³⁰ and R ⁵⁰ each represent -CH ₃ , and R ⁴⁰ represents -H).

¹ H-NMR (600 MHz, CD ₃ OD, 300 K) δ (ppm): 1.96 (quint, J=7.1 Hz, 2H, -CH ₂ -), 2.16 (s, 3H, CH ₃ ), 2.24 (s, 3H, CH ₃ ), 3.20 (t, J=7.1Hz, 2H, -CH ₂ -), 5.83 (s, 1H, CH), 8.05 (s, 1H, NH)
¹³ C{ ¹ H}-NMR (125 MHz, CD ₃ OD, 300K) δ (ppm): 10.8 (S), 13.2 (S), 30.9 (S), 36.3 (S), 46.7 (S), 106.1 (S), 141.1 (S), 148.7 (S), 163.9 (S)

As shown in Table 4, in Example 29, in which 3-amino-1-propanol was used as the compound having an amino group and a hydroxy group, the hydroxyalkylcarboxamide compound represented by formula (60) was obtained in a high yield of 39%.

"Example 30"
Hydroxyalkylcarboxamide compounds were produced in the same manner as in Example 13, except that the reaction was carried out at the reaction temperature shown in Table 5.
Table 5 shows the carbamic acid ester, blocking agent, activating agent, type and amount of solvent used, reaction temperature, and reaction time used in the carboxamide compound synthesis process.
For the hydroxyalkylcarboxamide compound obtained by the production method of Example 30, the yield was calculated in the same manner as in Example 1. The results are shown in Table 5. For comparison, Table 5 also shows the results of Example 13 shown in Table 2.

The structure of the hydroxyalkylcarboxamide compound obtained by the production method of Example 30 was identified in the same manner as in Example 1.
As a result, it was confirmed that the hydroxyalkylcarboxamide compound obtained by the production method of Example 30 was the hydroxyalkylcarboxamide compound represented by formula (16).

As shown in Table 5, in Example 13, where the reaction temperature was 150°C, the hydroxyalkylcarboxamide compound represented by formula (16) was obtained in a higher yield than in Example 30, where the reaction temperature was 130°C.

"Example 31"
Hydroxyalkylcarboxamide compounds were produced in the same manner as in Example 12, except that the reaction was carried out at the reaction temperature shown in Table 5.
Table 5 shows the carbamic acid ester, blocking agent, activating agent, type and amount of solvent used, reaction temperature, and reaction time used in the carboxamide compound synthesis process.
For the hydroxyalkylcarboxamide compound obtained by the production method of Example 31, the yield was calculated in the same manner as in Example 1. The results are shown in Table 5. For comparison, Table 5 also shows the results of Example 12 shown in Table 2.

The structure of the hydroxyalkylcarboxamide compound obtained by the production method of Example 31 was identified in the same manner as in Example 1.
As a result, it was confirmed that the hydroxyalkylcarboxamide compound obtained by the production method of Example 31 was the hydroxyalkylcarboxamide compound represented by formula (16).

As shown in Table 5, in Example 12, where the reaction temperature was 150°C, the hydroxyalkylcarboxamide compound represented by formula (16) was obtained in a higher yield than in Example 31, where the reaction temperature was 100°C.

"Example 32"
A hydroxyalkylcarboxamide compound was produced in the same manner as in Example 12, except that trifluoromethanesulfonic acid (TfOH) (manufactured by Tokyo Chemical Industry Co., Ltd.) was used as the activating agent.
Table 5 shows the carbamic acid ester, blocking agent, activating agent, type and amount of solvent used, reaction temperature, and reaction time used in the carboxamide compound synthesis process.
For the hydroxyalkylcarboxamide compound obtained by the production method of Example 32, the yield was calculated in the same manner as in Example 1. The results are shown in Table 5.

The structure of the hydroxyalkylcarboxamide compound obtained by the production method of Example 32 was identified in the same manner as in Example 1.
As a result, it was confirmed that the hydroxyalkylcarboxamide compound obtained by the production method of Example 32 was the hydroxyalkylcarboxamide compound represented by formula (16).

The present invention can be used as a material for a variety of compounds having multiple functional groups, and as a method for producing the same.

Claims (9)

A method for producing a hydroxyalkylcarboxamide compound represented by the following general formula (6), comprising a first step of reacting one or both of a carbamic acid ester represented by the following general formula (3) and a cyclized product of the carbamic acid ester represented by the following general formula (4) with a blocking agent containing a pyrazole ring represented by the following general formula (5) in the presence of a solvent to synthesize a compound represented by the following general formula (6):

(In formula (3), R ¹ represents -CH ₃ or -CH ₂ -CH _3. In formulas (3), (4) and (6), R ² represents a linear alkylene group having 2 to 6 carbon atoms or a cycloalkylene group having 4 to 6 carbon atoms. In formulas (5) and (6), R ³ and R ⁵ each represent -H, -CH ₃ or -CH ₂ -CH ₃ , and R ⁴ represents -H. In formula (5), X represents a hydrogen atom or an alkali metal atom.)
Prior to the first step,
The method for producing a hydroxyalkylcarboxamide compound according to claim 1, further comprising carrying out a second step of synthesizing either or both of a carbamic acid ester represented by the following general formula (3) and a cyclized product of a carbamic acid ester represented by the following general formula (4) by reacting a dialkyl carbonate represented by the following general formula (1) with a compound having an amino group and a hydroxy group represented by the following general formula (2):

(In formula (1) and formula (3), R ¹ represents -CH ₃ or -CH ₂ -CH _3. The two R ^1s in formula (1) are the same. In formulas (2) to (4), R 2 represents a linear alkylene group having 2 to 6 carbon atoms or a cycloalkylene group having 4 to 6 carbon atoms.) The method for producing a hydroxyalkylcarboxamide compound according to claim 1 or 2, characterized in that in formula (3), R ¹ represents -CH ₃ , in formulas (3), (4) and (6), R ² represents -CH ₂ -CH _{2 -} , and in formulas (5) and (6), R ³ and R ⁵ represent -CH 3, and R ⁴ represents -H. The method for producing a hydroxyalkylcarboxamide compound according to any one of claims 1 to 3, characterized in that in the first step, either one or both of the carbamic acid ester and the cyclized product are reacted with the blocking agent in the presence of an activating agent consisting of a base compound. The method for producing a hydroxyalkylcarboxamide compound according to claim 4, characterized in that the activator is one or more selected from the group consisting of alkali metal hydrides, alkaline earth metal hydrides, primary to tertiary alkoxides, alkali metal hydroxides, and alkali metal phosphates. The method for producing a hydroxyalkylcarboxamide compound according to claim 4, characterized in that the activator is any one selected from lithium methoxide, sodium methoxide, and sodium tert-butoxide. The method for producing a hydroxyalkylcarboxamide compound according to any one of claims 1 to 6, characterized in that in the first step, either or both of the carbamic acid ester and the cyclized product are reacted with the blocking agent in an amide solvent. The method for producing a hydroxyalkylcarboxamide compound according to claim 7, characterized in that the amide solvent is N,N-dimethylformamide. A hydroxyalkylcarboxamide compound represented by the following general formula (60):

(In formula (60), R ²⁰ represents -CH ₂ -CH ₂ -CH ₂ -. ^{R 30} and R ⁵⁰ each represent -H, -CH ₃ or -CH ₂ -CH ₃ , and R ⁴⁰ represents -H.)

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