JPS6023674B2 - Method for producing α-(N-silyl-N-substituted)carbamoylcarboxylic acid ester - Google Patents
Method for producing α-(N-silyl-N-substituted)carbamoylcarboxylic acid esterInfo
- Publication number
- JPS6023674B2 JPS6023674B2 JP10944676A JP10944676A JPS6023674B2 JP S6023674 B2 JPS6023674 B2 JP S6023674B2 JP 10944676 A JP10944676 A JP 10944676A JP 10944676 A JP10944676 A JP 10944676A JP S6023674 B2 JPS6023674 B2 JP S6023674B2
- Authority
- JP
- Japan
- Prior art keywords
- silyl
- substituted
- isocyanate
- acid ester
- producing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 title description 5
- 150000002148 esters Chemical class 0.000 title description 5
- 239000012948 isocyanate Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000002513 isocyanates Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 3
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims description 2
- -1 carbamyl carboxylic acid ester Chemical class 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XQJHRCVXRAJIDY-UHFFFAOYSA-N aminophosphine Chemical compound PN XQJHRCVXRAJIDY-UHFFFAOYSA-N 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 229940017219 methyl propionate Drugs 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- JNOGVQJEBGEKMG-UHFFFAOYSA-N (1-methoxy-2-methylprop-1-enoxy)-trimethylsilane Chemical compound COC(=C(C)C)O[Si](C)(C)C JNOGVQJEBGEKMG-UHFFFAOYSA-N 0.000 description 1
- CZQIJQFTRGDODI-UHFFFAOYSA-N 1-bromo-4-isocyanatobenzene Chemical compound BrC1=CC=C(N=C=O)C=C1 CZQIJQFTRGDODI-UHFFFAOYSA-N 0.000 description 1
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- GFNKTLQTQSALEJ-UHFFFAOYSA-N 1-isocyanato-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=O)C=C1 GFNKTLQTQSALEJ-UHFFFAOYSA-N 0.000 description 1
- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 description 1
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- OUPLTJDZPQZRBW-UHFFFAOYSA-N n-(oxomethylidene)methanesulfonamide Chemical compound CS(=O)(=O)N=C=O OUPLTJDZPQZRBW-UHFFFAOYSA-N 0.000 description 1
- HOKBIQDJCNTWST-UHFFFAOYSA-N phosphanylidenezinc;zinc Chemical compound [Zn].[Zn]=P.[Zn]=P HOKBIQDJCNTWST-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
【発明の詳細な説明】
本発明はＱ−（Ｎ−シリルーＮ一置換）カルバモィルカ
ルボン酸ヱステルを製造する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing Q-(N-silyl-N-monosubstituted)carbamoylcarboxylic acid esters.
更に詳しくはケテンシリルアセタールとイソシアナート
とを混合することによりＱ−（Ｎ−シリル−Ｎ−置換）
カルバモィルカルボン酸ェステルを製造する方法に関す
るものである。本発明の方法で製造されるＱ−（Ｎーシ
リル−置換）カルバモィルカルボン酸ェステルは一般式
（式中、Ｒ１、Ｒ２は水素、アルキル基、アリール基、
Ｒ３はアルキル基、アリール基または有機基をもつシリ
ル茎であり、Ｒ４、Ｒ５、Ｒ６はアルキル基、ァリール
基、Ｒ７はアルキル基、アリール基、スルホニル基また
は有機基を持つシリル基である。More specifically, by mixing ketene silylacetal and isocyanate, Q-(N-silyl-N-substituted)
The present invention relates to a method for producing carbamyl carboxylic acid ester. The Q-(N-silyl-substituted)carbamoylcarboxylic acid ester produced by the method of the present invention has the general formula (wherein R1 and R2 are hydrogen, an alkyl group, an aryl group,
R3 is a silyl stem with an alkyl group, aryl group or organic group, R4, R5, R6 are an alkyl group, aryl group, and R7 is a silyl group with an alkyl group, aryl group, sulfonyl group or organic group.
〕で表わされる化合物である。この化合物は加水分解あ
るいはアルコールとの反応により容易に対応するＱ−（
Ｎ−魔換）カルバモィルカルボン酸ェステルを誘導する
ことが出釆ろく参考例参照）他、シリルアミ／基をハロ
ゲン化物、ハロゲン化アシル、カルボニル化合物、ヘテ
ロクムレン化合物等との反応により、さらに複雑なへテ
ロ環化合物や生理活性物質に導くことが出釆る点で有用
な合成中間体である〔参考文献；Ｋ．ｌｔｏｈ、Ｎ．Ｋ
ａｔｏ ａｎｄＹ．ｌｓｈｉｉ、Ｇ．Ｃｈｅｍ．Ｓｏｃ
．、◎，１９６９、２００５：Ｋ．ｌｔｏｈ、Ａ．Ｎｏ
ｚａｗａ ａｎｄ Ｙ．ｌｓｈｊｉ 、Ｔｅｔｒａｈｅ
ｄｒｏｎＬｅｔｔ、１９６９、１４２１；特開昭５０−
７０３１４．〕。また、Ｑ−（Ｎ−置換）カルバモィル
カルポン酸ェステル類はアミド系の薬物として殺虫作用
を有するほか、スルホンアミドはサルフア剤として抗菌
作用または利尿剤としての作用も有している。従釆、こ
の種の化合物は■ェナミンとイソシアナートの反応〔Ｍ
．Ｅ．Ｋｎｅｈｎｅ、“Ｅ脇ｍｍｅｓ ｌｎ Ｃせ
餌ｎｉｃ Ｓｙｎ比ｅｓｉｓ ” ｉｎ“Ｅｎａｍｌ
ｎｅｓ”、Ａ．Ｇ．Ｃｏｏｋ、Ｅｄｔ．、Ｍａｒｃｅｌ
０にｋｋｅｒ、ＮｅｗＹｏｒｋｌ９６玖 ｐｐ３１３〜
４４９．〕あるいは■ジェステルとアミノホスフインと
の反応、〔Ｒ．Ｂｕｒｇａ船、Ｃｏｍｐｔ ｒｅ中．、
２５８、１５３２（１９６４）〕などによって合成され
ていたが■の方法では当モルのアミンが反応によって遊
離してくるのでこのものの分離操作が必要となるため煩
雑であり、収率も余り高くならない。■の方法では便用
しうるアミノホスフィンが例えばＨＭＰＡ〔（Ｍｅ２Ｎ
）３Ｐ〕のようなジアルキルアミノ基をもつアミノホス
フインに限定されてしまうので種々の置換基をもつこの
種の化合物を合成するのには採用出釆ない。本発明者等
はこのような欠点を鮫決すべくＱ−（Ｎ−シリル−Ｎ−
置換）カルバモイルカルボン酸ヱステルの製造法につい
て鋭意検討を重ねた結果、本発明を完成するに至ったも
のである。] This is a compound represented by This compound can be easily converted by hydrolysis or reaction with alcohol, Q-(
In addition, by reacting the silylamine/group with halides, acyl halides, carbonyl compounds, heterocumulene compounds, etc., more complex It is a useful synthetic intermediate because it can lead to heterocyclic compounds and physiologically active substances [References: K. ltoh, N. K
ato andY. Lshii, G. Chem. Soc.
．． , ◎, 1969, 2005: K. ltoh, A. No
Zawa and Y. lshji, Tetrahe
droneLett, 1969, 1421; Japanese Patent Application Publication No. 1973-
70314. ]. Furthermore, Q-(N-substituted)carbamoylcarboxylic acid esters have an insecticidal effect as an amide drug, and sulfonamides also have an antibacterial effect or a diuretic effect as a sulfur drug. Accordingly, this type of compound is the reaction between enamine and isocyanate [M
．． E. Knehne, “E side mmes ln C sebait nic Syn ratio” in “Enaml
nes”, A.G. Cook, Edt., Marcel
0 to kker, NewYorkl96ku pp313~
449. ] or ■ Reaction of gestel with aminophosphine [R. Burga ship, Comprehensive. ,
258, 1532 (1964)], but in the method (2), the equivalent mole of amine is liberated by the reaction, which requires a separation operation, which is complicated, and the yield is not very high. In method (2), the aminophosphine that can be used is, for example, HMPA [(Me2N
)3P] is limited to aminophosphine having a dialkylamino group, so it cannot be used to synthesize this kind of compounds having various substituents. In order to overcome these drawbacks, the present inventors have developed Q-(N-silyl-N-
The present invention has been completed as a result of extensive research into methods for producing (substituted) carbamoylcarboxylic acid esters.
本発明の方法によれば容易に種々のＱ−（Ｎーシリルー
Ｎ−置換）カルバモィルカルボン酸ェステルを創生物を
伴なわずに製造することが出来る。本発明を実施するに
あたり使用しうるィソシアナートとしてはメチルイソシ
アナート、アリルイソシアナート、ペンジルイソシアナ
ートの如きアルキルイソシアナート、フエニルイソシア
ナート、ｐーブロムフエニルイソシアナート、ｐークロ
ルフエニルイソシアナート、ｐ−トリルイソシアナート
、ｐ−ニトロフエニルイソシアナートの如きアリールイ
ソシアナート、Ｐ−トルエンスルホニルイソシアナート
、メタンスルホニルイソシアナートの如きスルホニルイ
ソシアナ−ト、トリメチルシリルィソシアナートの如き
シリルィソシアナート等を広範に例示することが出来る
。また、本発明で使用しうるもう一方の原料であるケテ
ンシリルアセタールは一般式ＲＩＲ２Ｃ＝Ｃ（ＯＲ３）
ＯＳｉＲ４Ｒ５Ｒ６（式中、Ｒ１、Ｒ２は水素、アルキ
ル基、アリール基、Ｒ３〜Ｒ６はアルキル基またはアリ
ール基を示す。According to the method of the present invention, various Q-(N-silyl-N-substituted)carbamoylcarboxylic acid esters can be easily produced without using a synthetic material. Isocyanates that can be used in carrying out the present invention include alkyl isocyanates such as methyl isocyanate, allyl isocyanate, pendyl isocyanate, phenyl isocyanate, p-bromphenyl isocyanate, and p-chlorophenyl isocyanate. , p-tolyl isocyanate, aryl isocyanate such as p-nitrophenyl isocyanate, sulfonyl isocyanate such as p-toluenesulfonyl isocyanate, methanesulfonyl isocyanate, silylysocyanate such as trimethylsilylysocyanate, etc. A wide range of examples can be given. In addition, ketene silyl acetal, which is another raw material that can be used in the present invention, has the general formula RIR2C=C(OR3).
OSiR4R5R6 (wherein R1 and R2 represent hydrogen, an alkyl group, or an aryl group, and R3 to R6 represent an alkyl group or an aryl group.
）で表わされる化合物であるが、このものは例えばトリ
オルガノクロルシランとカルポン酸ェステルとの反応に
より容易に合成することができる。本発明の方法によれ
ば、当モルのィソシアナートとケテンシリルアセタール
を無触媒、無溶媒で蝿梓混合し、室温〜１００ｑｏに加
湿することにより所望のＱ‐（Ｎ−シリル−Ｎ−置換）
カルバモイルカルボン酸ェステルを好収率で製造するこ
とが出来る。), which can be easily synthesized by, for example, reacting triorganochlorosilane with a carboxyl ester. According to the method of the present invention, the desired Q-(N-silyl-N-substituted) is obtained by mixing equimolar amounts of isocyanate and ketene silyl acetal without catalyst or solvent and humidifying the mixture to room temperature to 100 qo.
Carbamoyl carboxylic acid ester can be produced in good yield.
精製は反応混合物をそのまま減圧蒸留あるいは再結晶す
ることにより容易に行うことが出来る。尚、本反応は水
を嫌うので無水条件下で反応を行うことが望ましい。以
下、参考例及び実施例により本発明を更に詳細に説明す
る。Purification can be easily carried out by directly distilling the reaction mixture under reduced pressure or recrystallizing it. Note that this reaction dislikes water, so it is desirable to carry out the reaction under anhydrous conditions. Hereinafter, the present invention will be explained in more detail with reference to Reference Examples and Examples.
実施例 １
１．７４夕（０．０１モル）のジメチルケテンメチルト
リメチルシリルアセタールと１．１９夕（０．０１モル
）のフェニルィソシアナートとを混合し、油浴で７５℃
に加溢し、２独特間蝿拝した。Example 1 1.74 mol (0.01 mol) of dimethylketene methyltrimethylsilyl acetal and 1.19 mol (0.01 mol) of phenyl isocyanate were mixed and heated at 75°C in an oil bath.
There was a lot of trouble, and I worshiped the flies for two unique moments.
。反応終了後反応混合物を蒸留したところ沸点搬℃／０
．２２側Ｈｇを有するＱ−（ＮートリメチルシリルーＮ
ーフェニル）カルバモィル−Ｑーメチルプロピオン酸メ
チル２．１１夕（収率７２％）を得た。実施例 ２〜７
各種のケテンシリルアセタール及びィソシアナートを用
い、実施例１と同様に操作して相当するＱ−（Ｎ一二置
換カルバモィル）カルボン酸ヱステルを得た。. After the reaction was completed, the reaction mixture was distilled and the boiling point was ℃/0
．． Q-(N-trimethylsilyl-N with 22 side Hg
-Phenyl)carbamoyl-Q-methylpropionate 2.11 units (yield 72%) was obtained. Examples 2 to 7 Corresponding Q-(N-disubstituted carbamoyl)carboxylic acid esters were obtained in the same manner as in Example 1 using various ketene silylacetals and isocyanates.
条件及び結果は第１表の通りである。脳
雛
参考例
２．００夕のＱ一（ＮートリメチルシリルーＮーフェニ
ル）カルバモィル−Ｑ−メチルプロピオン酸メチル２叫
のメタノールを加え、室温で１０分間燈拝した。The conditions and results are shown in Table 1. Brain Chick Reference Example 2.00 ml of methyl Q-(N-trimethylsilyl-N-phenyl)carbamoyl-Q-methylpropionate was added with 2 ml of methanol and allowed to stand at room temperature for 10 minutes.
Claims (1)
させることを特徴とするα−（Ｎ−シリル−Ｎ−置換）
カルバモイルカルボン酸エステルを製造する方法。 ２ 反応を無水の条件下で行うことから成る特許請求の
範囲第１項に記載の方法。[Claims] 1. α-(N-silyl-N-substituted) characterized by reacting a ketene silylacetal with an isocyanate.
A method for producing carbamoyl carboxylic acid ester. 2. A process according to claim 1, which comprises carrying out the reaction under anhydrous conditions.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10944676A JPS6023674B2 (en) | 1976-09-14 | 1976-09-14 | Method for producing α-(N-silyl-N-substituted)carbamoylcarboxylic acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10944676A JPS6023674B2 (en) | 1976-09-14 | 1976-09-14 | Method for producing α-(N-silyl-N-substituted)carbamoylcarboxylic acid ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5334758A JPS5334758A (en) | 1978-03-31 |
| JPS6023674B2 true JPS6023674B2 (en) | 1985-06-08 |
Family
ID=14510436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10944676A Expired JPS6023674B2 (en) | 1976-09-14 | 1976-09-14 | Method for producing α-(N-silyl-N-substituted)carbamoylcarboxylic acid ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6023674B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0619359B2 (en) * | 1989-04-11 | 1994-03-16 | 出光石油化学株式会社 | Liquid sample analyzer |
-
1976
- 1976-09-14 JP JP10944676A patent/JPS6023674B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5334758A (en) | 1978-03-31 |
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