JPH0555490B2 - - Google Patents

Description

[Detailed description of the invention]

(Field of Industrial Application) The present invention provides a novel method for producing amide compounds useful as medicines and agricultural chemicals, or raw materials and intermediates thereof. (Prior Art and Problems to be Solved by the Invention) The present inventors have been conducting research on the synthesis of N-substituted-amide compounds using Schiff's base compounds as raw materials and their physiological activities. For example, in JP-A No. 60-4181, the present inventors proposed the general formula (However, W is a halogen atom, an alkoxy group,
or an alkylthio group, and -R ₄ , R ₅ and R ₆ each represent the same or different hydrogen atom, halogen atom, alkyl group, alkoxy group or alkylthio group. ) was proposed to be extremely useful as a herbicide. The method for producing the N-substituted-chloroacetanilide is as follows:
Generally, it is synthesized using a Schiff base compound as a raw material through a reduction step followed by a chloroacetylation step as shown in the formula below. In other words, if a Schiff base compound is used as a raw material, a two-step reaction must be carried out to reach the desired product, and in some cases, expensive and difficult-to-handle reagents such as lithium aluminum hydride must be used for reduction. After that, as a result of intensive research by the present inventors, it became possible to synthesize an amide compound in one step by reacting a Schiff base compound, a silane compound, and a carboxylic acid derivative. However, when producing it on an industrial level, it has disadvantages such as requiring a silane compound in an amount of 2 to 5 times the molar amount of the Schiff base compound and requiring a long reaction time. (Means and Effects for Solving the Problems) The present inventors have conducted extensive research in order to overcome the above-mentioned drawbacks in the method for synthesizing the amide compound.
As a result, when a Schiff base compound, a silane compound, and a carboxylic acid derivative are reacted, by using a catalytic amount of metal or metal halide, it is possible to use only about 1.0 to 1.5 times the mole of the silane compound relative to the Schiff base compound. They discovered that amide compounds can be synthesized in high yield and purity in a short period of time, leading to the completion of the present invention. That is, the present invention provides (a) general formula ()

[Formula] (where R is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group,
Represents a substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted cycloalkenyl group, or substituted or unsubstituted heterocycloalkyl group, R ₁ is Alkoxy group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted cyclo Represents an alkyl group, a substituted or unsubstituted cycloalkenyl group, or a substituted or unsubstituted heterocycloalkyl group, R ₂ is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group , a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, or a substituted or unsubstituted heterocycloalkyl group. ), (b) a silane compound represented by the general formula ( ) HSiXYZ (where X, Y, and Z represent the same or different hydrogen atoms or halogen atoms), and (c) a silane compound represented by the general formula ( ) R ₃ COA (However, R ₃ is the same as R ₁ above, and A is a halogen atom or

[Formula] represents a group. ) A carboxylic acid derivative represented by (d) general formula () M (Em) (where M represents an alkali metal, alkaline earth metal, copper, silver, iron, zinc or boron atom, and E represents a halogen atom). and m is an integer of 0 to 4). (However, R, R ₁ , R ₂ and R ₃ have the same meanings as above.) This is a method for producing an amide compound represented by: The Schiff base compound, which is one of the raw materials in the present invention, has the general formula (), that is,

It is a compound represented by the formula: Various organic groups are known as the groups represented by R, R ₁ and R ₂ in the above general formula (), and these organic groups can be used in the present invention without particular limitation. Generally preferably used R, R ₁ and
R ₂ is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted It represents a cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, or a substituted or unsubstituted heterocycloalkyl group. More specific examples of the organic groups widely used industrially include the following. Examples of the unsubstituted alkyl group include linear or branched alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl. Examples of the substituted alkyl group include linear or branched alkyl groups such as fluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, chloroethyl, bromoethyl, fluoropropyl, chloropropyl, butyl iodide, bromopentyl, chlorohexyl, and fluorooctyl. Branched haloalkyl group; methoxymethyl, methoxyethyl, methoxypropyl, methoxybutyl, methoxypentyl, methoxyhexyl, ethoxymethyl, ethoxyethyl, ethoxypropyl, ethoxybutyl, propoxymethyl, propoxyethyl, propoxypropyl, propoxybutyl, butoxymethyl, Linear or branched alkoxyalkyl groups such as butoxyethyl, butoxypropyl, butoxybutyl and pentoxybutyl; phenoxyalkyl groups such as phenoxymethyl, phenoxyethyl and chlorophenoxypropyl; cyanoethyl, cyanopropyl and cyanobutyl groups, etc. cyanoalkyl groups; nitroalkyl groups such as nitroethyl, nitropropyl and nitrohexyl;
Alkylthioalkyl groups such as methylthiomethyl, methylthioethyl, methylthiopropyl, ethylthiomethyl, ethylthioethyl, ethylthiobutyl and propylthioethyl; arylalkyl groups such as phenylmethyl, phenylethyl, phenylpropyl and methylphenylmethyl; thienylmethyl Heteroarylalkyl groups such as , thienylethyl, methoxythienylmethyl, furylmethyl, furylethyl, chlorofurylmethyl, pyrrolylmethyl and pyrazolylmethyl; cycloalkylalkyl groups such as cyclopropylmethyl and cyclohexylethyl; methoxycarbonylmethyl, methoxycarbonylethyl, Examples include alkoxycarbonyl alkyl groups such as ethoxycarbonylmethyl, ethoxycarbonylethyl, and ethoxycarbonylpropyl. The unsubstituted alkenyl group includes ethenyl,
Various regioisomeric alkenyl groups such as propenyl, butenyl, pentenyl, hexenyl and octenyl are mentioned. Examples of the substituted alkenyl group include haloalkenyl groups such as chloroethenyl, fluoroethenyl, bromopropenyl, iodide butenyl, chlorpentenyl, and fluorohexenyl; methoxyethenyl, methoxypropenyl, ethoxybutenyl, ethoxyhexenyl, and propoxybutenyl; Alkoxyalkenyl groups; examples include cyanoethenyl, nitropropenyl, dimethylaminoethenyl and methylthiopropenyl. Furthermore, examples of the unsubstituted alkynyl group include ethynyl, propynyl, butynyl, pentynyl, and hexynyl. Further, examples of the substituted alkynyl group include chloropropynyl, bromobutynyl, methoxybutynyl, cyanopropynyl, and methylthiobutynyl. Furthermore, examples of the unsubstituted aryl group include phenyl, naphthyl, anthranyl, and phenanthrenyl. In addition, examples of the substituted aryl group include methylphenyl, dimethylphenyl,
Ethyl phenyl, diethyl phenyl, propylphenyl, dipropylphenyl, butylphenyl,
Alkylphenyl groups such as pentylphenyl, hexylphenyl, methylethylphenyl, methylpropylphenyl and ethylpropylphenyl; fluorophenyl, difluorophenyl, chlorophenyl, dichlorophenyl, bromophenyl, phenyl iodide, trichlorophenyl and halophenyl groups such as chlorofluorophenyl; alkoxyphenyl groups such as methoxyphenyl, dimethoxyphenyl, trimethoxyphenyl, ethoxyphenyl, diethoxyphenyl, propoxyphenyl and butoxyphenyl; cyanophenyl, nitrophenyl, chloro( methyl) phenyl, chloro(ethoxy) phenyl, methyl (methoxy) phenyl,
Substituted phenyl groups such as methylthiophenyl, trifluoromethylphenyl, bis(chloroethylamino)phenyl, nitro(methyl)phenyl and diphenyl; methylnaphthyl, ethylnaphthyl, chloronaphthyl, dichloronaphthyl, methoxynaphthyl, methylthionaphthyl, nitro Examples include substituted naphthyl groups such as naphthyl and cyanonaphthyl. Furthermore, examples of the unsubstituted heteroaryl group include furyl, thienyl, pyrrolyl, pyridyl, pyrimidyl, benzofuryl, benzothienyl, indolyl, quinolyl, thiazolyl, pyrazolyl, benzothiazolyl, thiadiazolyl, and oxazolyl. Examples of the substituted heteroaryl group include methylfuryl, dimethylfuryl, ethylfuryl, propylfuryl, chlorofuryl, bromofuryl, methoxyfuryl, ethoxyfuryl,
Substituted furyl groups such as propoxyfuryl, methylthiofuryl, ethylthiofuryl, and nitrofuryl; methylthienyl, ethylthienyl, propylthienyl, butylthienyl, fluorothienyl, chlorothienyl, bromothienyl, thienyl iodide, methoxythienyl, ethoxythienyl, propoxy Substituted thienyl groups such as thienyl, methylthiothienyl, ethylthiothienyl and nitrothienyl; N-
Methylpyrrolyl, N-ethylpyrrolyl, methyl-
Substituted pyrrolyl groups such as N-methylpyrrolyl, chloro-N-ethylpyrrolyl, methoxy-N-methylpyrrolyl, methoxypyrrolyl, ethylpyrrolyl and chloropyrrolyl; substituted pyridyl groups such as methylpyridyl, ethylpyridyl, chloropyridyl and methoxypyridyl; methylbenzofuryl, Substituted benzofuryl groups such as chlorobenzofuryl, ethoxybenzofuryl and nitrobenzofuryl; substituted benzothienyl groups such as ethylbenzothienyl, fluorobenzothienyl, methoxybenzothienyl and nitrobenzothienyl; methylquinolyl, ethylquinolyl, chloroquinolyl and methoxyquinolyl, etc. Substituted quinolyl group; methylthiazolyl group and the like. Furthermore, examples of the unsubstituted cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Also,
The substituted cycloalkyl group includes methylcyclopropyl, ethylcyclopropyl, propylcyclopropyl, chlorocyclopropyl, methoxycyclopropyl, ethoxycyclopropyl, methylcyclobutyl, bromocyclobutyl, methylthiocyclobutyl, chlorocyclopentyl, methylcyclohexyl, Examples include ethylcyclohexyl, chlorocyclohexyl, methoxycyclohexyl and propoxycyclohexyl. Examples of unsubstituted cycloalkenyl groups include cyclobutenyl, cyclopentenyl and cyclohexenyl. Examples of the substituted cycloalkenyl group include methylcyclobutenyl, chlorocyclopentenyl, methoxycyclopentenyl, methylcyclohexenyl, ethylcyclohexenyl, chlorocyclohexenyl, methoxycyclohexenyl, and ethoxycyclohexenyl. Furthermore, examples of the unsubstituted heterocycloalkyl group include tetrahydrofuryl, tetrahydrothienyl, pyrrolidyl, tetrahydropyryl, tetrahydrothiopyryl, piperidyl, and the like. Further, examples of the substituted heterocycloalkyl group include N-methylpyrrolidyl, N-ethylpyrrolidyl, N-methylpiperidyl, and N-ethylpiperidyl. Furthermore, the alkyl group of the alkoxy group represented by R ₁ has the same meaning as the alkyl group described above. Specific examples of the alkoxy groups that are widely used industrially include methoxy, ethoxy, propoxy, butoxy, and pentoxy. In many cases, various positional isomers exist in the compounds having the groups listed above, but these can be used in the present invention without particular limitation. For example, as a methylphenyl group, O-methylphenyl group, m
-methylphenyl group and P-methylphenyl group, butyl group includes n-butyl group, sec
-butyl group and tert-butyl group. Furthermore, the substituents are not limited to the above specific examples, and can be appropriately selected and used as necessary, as long as the desired amide compound can be obtained by the production method of the present invention. Another raw material of the present invention is a silane compound represented by the general formula (), that is, HSiXYZ. In the general formula (), X, Y and Z may be the same or different hydrogen atoms or halogen atoms without particular limitation. As the halogen atom,
Each atom of chlorine, bromine, iodine or fluorine can be used without particular limitation, but chlorine and bromine atoms are particularly preferred. Specific examples of the above-mentioned silane compounds that are particularly preferably used industrially include HSiCl ₃ ,
These are compounds such as HSiBr ₃ , H ₂ SiCl ₂ , H ₂ SiBr ₂ and H ₃ SiBr. Another raw material of the present invention is a carboxylic acid derivative represented by the general formula (), ie, R ₃ COA. R ₃ in the carboxylic acid derivative is a substituent defined similarly to R, R ₁ or R ₂ in the above general formula (). In the above general formula (), A is a halogen atom or

[Formula] is a group. When A is a halogen atom, R ₃ COA represents an acid halide, and the halogen atom may be a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom without particular limitation. Industrially, acid chloride or acid bromide in which A is a chlorine atom or a bromine atom are particularly preferably used. Also, A

[Formula] When represented by a group, that is,

[Formula] represents an acid anhydride. Specific examples of acid halides that are generally suitable for industrial use include acetic acid chloride, acetic bromide, chloroacetic acid chloride, dichloroacetic acid chloride, bromoacetic acid bromide, iodoacetic acid chloride, and dibromoacetic acid. Chloride, methoxyacetic acid chloride, cyanoacetic acid chloride, trifluoroacetic acid fluoride, phenoxyacetic acid chloride, chlorophenoxyacetic acid chloride, propionic acid chloride, chloropropionic acid chloride, bromopropionic acid bromide, butyric acid chloride, chlorobutyric acid chloride,
Valeric acid chloride, chlorovaleric acid chloride, hexanoic acid chloride, acrylic acid chloride, butenoic acid chloride, chlorobutenoic acid chloride,
Pentenoyl chloride, chloropentenoyl chloride, propionic acid chloride, phenylpropionic acid chloride, phenylpropenoyl chloride, furyl acrylic acid chloride, benzoic acid chloride, benzoic acid bromide, methylbenzoic acid chloride, ethylbenzoic acid bromide, chlorobenzoic acid Acid chloride, fluorobenzoic acid fluoride, methoxybenzoic acid chloride, chloro(methyl)benzoic acid chloride, cyanobenzoic acid chloride, phenylbenzoic acid chloride, nitrobenzoic acid chloride, furoyl chloride, thiophenecarboxylic acid chloride, indolecarboxylic acid chloride , picolinic acid chloride, cyclopropanecarboxylic acid chloride, etc. are suitable. Further, as the acid anhydride, acetic anhydride, propionic anhydride, trifluoroacetic anhydride, chloroacetic anhydride, benzoic anhydride, etc. are preferably used. One of the other features of the present invention is the general formula ()
That is, a metal or a metal halide represented by M (Em) is used as a catalyst.
In the above general formula (), M is an alkali metal such as lithium, sodium and potassium, an earth metal such as beryllium, magnesium, calcium and barium, copper, silver, iron, zinc or a boron atom,
E may be a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom without particular limitation. Metals that are industrial and have high catalytic ability include lithium, magnesium, barium, copper, silver, iron, etc. Metal halides include lithium fluoride, lithium chloride, lithium bromide, lithium iodide, Sodium iodide, potassium iodide, beryllium chloride, beryllium bromide, magnesium chloride, calcium bromide, barium chloride, copper chloride, copper bromide, copper iodide, silver chloride, silver bromide, silver chloride, iron bromide, Examples include zinc chloride, zinc bromide, and boron trichloride. Although the reaction of the raw materials in the present invention can be carried out without a solvent, it is generally preferable to carry out the reaction in a solvent. The solvent can be used without limitation as long as it is an inert organic solvent that does not interact with coexisting raw materials such as silane compounds and carboxylic acid derivatives. Generally, benzene, toluene, chloroform, acetonitrile, etc. are preferably used.
The molar ratio of the raw materials to be charged in this reaction is not particularly limited, but considering the increase in by-products and economic efficiency, 1 to 1.5 moles of the silane compound and 1 to 1.5 moles of the silane compound to 1 mole of the Schiff base compound, Preference is given to using a proportion of 1 to 1.2 mol of derivative and 0.001 to 0.20 atoms of metal or 0.001 to 0.20 mol of metal halide. In particular, when a large amount of carboxylic acid derivative is used, side reactions tend to occur more easily, so it is preferable to determine the molar ratio of the raw materials to be charged in advance. Note that the Schiff base compound that is the raw material used in the present invention does not necessarily have to be isolated and purified. That is, a Schiff base compound is synthesized from an aldehyde or a ketone and an amine by azeotropic dehydration, etc., and then the other raw materials used in the present invention, such as a silane compound, a carboxylic acid derivative, and a metal or metal halide, are added and reacted. Good too. In addition, the reaction temperature in the above reaction is not particularly limited and can be selected within a wide temperature range, but the reaction is carried out at a suitable temperature range taking into account the chemical reactivity of the raw materials and the stability of the amide compound that is the product. It is preferable. In general, it may be selected from the range of -20°C to 150°C. Furthermore, although the reaction time varies depending on the reaction temperature, it can generally be selected from several minutes to several days, for example from 5 minutes to 10 days. The order in which the raw materials and catalysts represented by the general formulas (), (), (), and () of the present invention are added is not particularly limited and may be selected as necessary. Generally, the silane compound and carboxylic acid derivative may be added to the Schiff base compound and the metal or metal halide at room temperature or under cooling. In these cases,
Generally, a solvent is often used, and the four components of metal or metal halide, Schiff base compound, silane compound, and carboxylic acid derivative may be added and reacted in the solvent, and each component is dissolved in the solvent.
These solutions may be added and mixed to react. In the present invention, an amide compound can be easily obtained by reacting each raw material represented by the general formulas () to () above in the presence of a catalyst of the general formula (). The method for purifying the amide compound obtained by the above reaction is not particularly limited. Generally, after completion of the reaction, distillation at normal pressure, reduced pressure or vacuum may be carried out, and purification methods such as washing, recrystallization or chromatography may also be used as necessary. In addition, when the amide compound has a high boiling point, after the completion of the reaction, remove low boiling point components such as the solvent, dissolve it in the solvent again, wash with water, wash with a dilute aqueous alkaline solution, and then remove the solvent. Easily removes unreacted silane compounds, carboxylic acid derivatives, and by-product silane compounds,
The desired amide compound can also be obtained industrially in a pure manner. (Effects of the present invention) The amide compound obtained by the method of the present invention is
For example, it is useful for agricultural chemicals such as herbicides, insecticides, and fungicides, or for pharmaceuticals. It is also a useful substance as an intermediate raw material for these uses. When synthesizing an amide compound, if the method of the present invention is used, the Schiff base compound will have a 1.0 to 1.5
By simply using about double the molar amount of the silane compound, it can be obtained in a short time with high yield and high purity. Therefore, it can be said that the present invention is extremely excellent from an industrial perspective. (Examples) Examples and comparative examples are given below to specifically explain the present invention, but the present invention is not limited to these examples. Example 1 N-[2'-(3'-methoxy)-
750 g (3.06 mole) of thienylmethylidene-2,6-dimethylaniline in dry benzene (2000 ml)
Add the solution and 0.5g (0.01mole) of lithium chloride,
trichlorosilane with stirring at room temperature under nitrogen.
490g (3.61mole) and chloroacetyl chloride
A solution of 363 g (3.21 mole) in dry benzene in 500 ml was slowly added. After stirring at room temperature for 30 minutes, the reaction solution was neutralized with a dilute aqueous alkali solution, and the amount of benzene was separated. The separated benzene layer was washed with water and then dried over anhydrous sodium sulfate. By distilling off the benzene and drying under vacuum, N-[2'-(3'-methoxy)-thienylmethyl]-, which is a pale solid, is obtained.
α-chloroaceto-2,6-dimethylanilide
988 g (3.05 mole) was obtained. The yield is N-[2'-(3'-
methoxy)-thienylmethylidene]-2,6-dimethylaniline, and the purity of the product was 99.3%. Example 2 Cupric chloride was used as a catalyst in place of lithium chloride in an amount of 0.01 times the molar amount of N-[2'-(3'-methoxy)-thienylmethylidene)]-2,6-dimethylaniline, and Using 1.02 times the mole of chloroacetic anhydride instead of chloroacetyl chloride, and using acetonitrile instead of benzene as the solvent,
The same reaction as in Example 1 was carried out. After the reaction was completed, the viscous liquid obtained by removing the low boiling point components became solid when vacuum dried. By crystallizing the compound using hexane, N-[2'-(3'-methoxy)-thienylmethyl]-α-chloroaceto-
White crystals of 2,6-dimethylanilide were obtained. The yield is 98.8 based on N-[2'-(3'-methoxy)-thienylmethylidene]-2,6-dimethylaniline.
%, and the purity was 98.9%. Comparative example: In a three-neck flask, N-[2'-(3'-methoxy)
-thienylmethylidene]-2,6-dimethylaniline 250 g (1.02 mole) of dry benzene (2000
ml) solution and stirred at room temperature under nitrogen.
A solution of 320 g (2.36 mole) trichlorosilane in dry benzene (300 ml) was added slowly. After stirring at room temperature for 2 hours, the low-boiling components were distilled off and the resulting viscous liquid was dissolved again in benzene (1500 ml). The benzene solution was washed with water and a dilute aqueous alkali solution, and then dried over anhydrous sodium sulfate. The viscous liquid obtained by distilling off the benzene was dried under vacuum to obtain N-[2'-(3'-methoxy)-thienylmethyl]-α-chloroaceto-2, which is a pale solid.
290 g (0.90 mole) of 6-dimethylanilide was obtained. The yield was 88.2% based on N-[2'-(3'-methoxy)-thienylmethylidene]-2,6-dimethylaniline, and the purity was 92.8%. Example 3 2-acetylthiophene 40g (0.32mole), 2
- Azeotropic dehydration was performed by heating a mixture of 34 g (0.32 mole) of methylaniline and toluene (150 ml) under reflux on an oil bath for 1 hour. Add 0.3 g of lithium chloride (7.1×
10 ^-3 mole), then 36.2 g (0.32 mole) of chloroacetyl chloride and 47.3 g (0.32 mole) of trichlorosilane.
A solution of 0.35 g (0.35 mole) in dry benzene (50 ml) was added dropwise, and the mixture was reacted for 1 hour. The reaction solution was prepared in Example 1.
A pale yellow solid compound having the structural formula shown below was obtained as crude crystals.
The crystals were vacuum distilled to a boiling point of 167℃/0.15mm.
89.5g (0.31mole) of white solid which is a fraction of Hg
Obtained. Yield is based on 2-acetylthiophene
The purity was 99.8%. Example 4 Using a method similar to that described in Examples 1, 2, and 3, 1.15 times the mole of the silane compound, 1.02 times the mole of the carboxylic acid derivative, and a metal or metal halide were added as raw materials to 1 mole of the Schiff base compound.
Using 0.005 times the molar amount, various amide compounds were synthesized by conducting the reaction at room temperature for 2 hours. The structure and yield of the product as well as the type of silane compound and metal or metal halide catalyst used are listed in Table 1. In all cases, both yield and purity were higher than when the reaction was carried out without a catalyst.

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Claims (1)

[Claims] 1 (a) General formula () [Formula] (where R is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group,
Represents a substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted cycloalkenyl group, or substituted or unsubstituted heterocycloalkyl group, R ₁ is Alkoxy group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted cyclo Represents an alkyl group, a substituted or unsubstituted cycloalkenyl group, or a substituted or unsubstituted heterocycloalkyl group, R ₂ is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group , a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, or a substituted or unsubstituted heterocycloalkyl group. ), (b) a silane compound represented by the general formula () HSiXYZ (where X, Y and Z represent the same or different hydrogen atoms or halogen atoms); and (c) a silane compound represented by the general formula () ) R ₈ COA (However, R ₈ is the same as R ₁ above, and A represents a halogen atom or a [formula] group.) The carboxylic acid derivative represented by (d) General formula () M (Em) (However, M represents an alkali metal, alkaline earth metal, copper, silver, iron, zinc or boron atom, E represents a halogen atom, and m is an integer from 0 to 4.) Metal or halogen represented by The general formula () is characterized by the reaction being carried out in the presence of a compound metal. (However, R, R ₁ , R ₂ and R ₈ have the same meanings as above.) A method for producing an amide compound represented by: