JPS6051186A - Preparation of 2-(n-cyanoimino)-3-cyanoethylthiazolidine - Google Patents

Preparation of 2-(n-cyanoimino)-3-cyanoethylthiazolidine

Info

Publication number
JPS6051186A
JPS6051186A JP15854583A JP15854583A JPS6051186A JP S6051186 A JPS6051186 A JP S6051186A JP 15854583 A JP15854583 A JP 15854583A JP 15854583 A JP15854583 A JP 15854583A JP S6051186 A JPS6051186 A JP S6051186A
Authority
JP
Japan
Prior art keywords
alkali metal
base
cyanoiminothiazolidine
solvent
cyanoimino
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.)
Granted
Application number
JP15854583A
Other languages
Japanese (ja)
Other versions
JPH0477749B2 (en
Inventor
Dotaro Fujimoto
藤本　導太郎
Giichi Funatsukuri
船造　義一
Masatoshi Sakae
栄　雅敏
Takeshi Sakai
酒井　武司
Shuhei Takamatsu
高松　修平
Masanori Katsurada
正徳 桂田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fujimoto Pharmaceutical Corp
Original Assignee
Fujimoto Pharmaceutical Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Fujimoto Pharmaceutical Corp filed Critical Fujimoto Pharmaceutical Corp
Priority to JP15854583A priority Critical patent/JPS6051186A/en
Publication of JPS6051186A publication Critical patent/JPS6051186A/en
Publication of JPH0477749B2 publication Critical patent/JPH0477749B2/ja
Granted legal-status Critical Current

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  • Thiazole And Isothizaole Compounds (AREA)

Abstract

PURPOSE:To obtain the titled compound useful as a raw material for synthesizing an antagonist with H2 receptor, repellent, etc. efficiently, by reacting N- cyanoiminothiazolidine with acrylonitrile in a solvent in the presence of a base. CONSTITUTION:N-Cyanoiminothiazolidine shown by the formula I is reacted with acrylonitrile in a solvent (preferably alcohol, dioxane, DMF, dimethyl sulfoxide, or acetone) in the presence of a base (strong base such as preferably alkali metal hydroxide, alkali metal alkoxide, alkali metal hydride, etc.) preferably at room temperature-50 deg.C, to give the desired compound shown by the formula II.

Description

【発明の詳細な説明】 本発明は、下式で示される２−（Ｎ−シアノイミノ）−
３−シアノエチルチアゾリジンの製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention provides 2-(N-cyanoimino)- represented by the following formula.
The present invention relates to a method for producing 3-cyanoethylthiazolidine.

化合物１コ圧〕は、例えばＩ（２レセプター拮抗剤や駆
虫剤などの合成原料として有用である。Compound 1] is useful as a synthetic raw material for, for example, I(2 receptor antagonists and anthelmintics).

本発明方法によれば、式〔Ｉ〕： で示されるＮ−シアノイミノチアソリシンと、アクリロ
ニトリル（ＣＨ２＝　Ｃｌ−１−ＯＮ　）とを溶媒中、
塩基の存在下に反応させることにより、目的化合物（Ｉ
ｔ）が得られる。According to the method of the present invention, N-cyanoiminothiasoricin represented by formula [I]: and acrylonitrile (CH2=Cl-1-ON) are mixed in a solvent,
By reacting in the presence of a base, the target compound (I
t) is obtained.

溶媒は、例えばアルコール、ジオキサン、ジメチルホル
ムアミド、ジメチルスルホキシド、アセトンなどが好適
であり、塩基としてはアルカリ金属水酸化物、アルカリ
金属アルコキサイド、アルカリ金属水素化物などの強塩
基が適当である。反応は、室温ないし５０°Ｃの加温下
に効率よく進行する。Suitable solvents include, for example, alcohol, dioxane, dimethylformamide, dimethyl sulfoxide, and acetone, and suitable bases include strong bases such as alkali metal hydroxides, alkali metal alkoxides, and alkali metal hydrides. The reaction proceeds efficiently under heating at room temperature to 50°C.

実施例 ｔ−ブタノール１５０ｍ１にＮ−シアノイミノチアゾリ
ジン１２．７９　（０，１モル）を懸濁させ、これに３
０％水酸化カリウム（ＫＯＨ）のメタノール溶液０．６
６　ｍｌを加え、４０°Ｃに加温する。一方、ｔ−ブタ
ノール１０ｔｎｌにアクリロニ１〜リル１０９ｇ（０，
２０６モル）を溶かした溶液を準備し、これを上記反応
液に４０分を要して滴下する。温和終了後、その温度の
まま１時間攪拌する。反応液を留去し、残渣に水を加え
ると、２−（Ｎ−シアノイミノ）−３−シアノエチルチ
アゾリジンの結晶を得る。このものは十分に純品である
。収量１４．２　ｇ（、７８，８％）。融点８６°Ｃ。Example 12.79 (0.1 mol) of N-cyanoiminothiazolidine was suspended in 150 ml of t-butanol, and 3
0% potassium hydroxide (KOH) in methanol 0.6
Add 6 ml and warm to 40°C. On the other hand, in 10 tnl of t-butanol, 109 g of acryloni
A solution of 206 mol) is prepared and added dropwise to the above reaction solution over a period of 40 minutes. After warming, stir at that temperature for 1 hour. The reaction solution is distilled off and water is added to the residue to obtain crystals of 2-(N-cyanoimino)-3-cyanoethylthiazolidine. This stuff is pure enough. Yield 14.2 g (,78.8%). Melting point: 86°C.

ＩＲνｍａＸ（Ｎｕｊｏｌ）：２２４４．２１８３．１
５８０．１４５０．１３６５．１２６０．１　０　６　
５（Ｃ＋ａ　＋）　。IRνmaX(Nujol):2244.2183.1
580.1450.1365.1260.1 0 6
5(C+a+).

代理人　弁理士　宮　崎　新八部Agent: Patent Attorney Shinhachibe Miyazaki

Claims (1)

【特許請求の範囲】[Claims] （１）Ｎ−シアノイミノチアゾリジンとアクリロニｌ−
ＩＪルを、溶媒中、塩基の存在下に反応させることを特
徴とする２−（Ｎ−シアノイミノ）−３−シアノエチル
チアプリジンの製造法。(1) N-cyanoiminothiazolidine and acryloni l-
A method for producing 2-(N-cyanoimino)-3-cyanoethylthiapridine, which comprises reacting IJ1 in a solvent in the presence of a base.
JP15854583A 1983-08-30 1983-08-30 Preparation of 2-(n-cyanoimino)-3-cyanoethylthiazolidine Granted JPS6051186A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP15854583A JPS6051186A (en) 1983-08-30 1983-08-30 Preparation of 2-(n-cyanoimino)-3-cyanoethylthiazolidine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP15854583A JPS6051186A (en) 1983-08-30 1983-08-30 Preparation of 2-(n-cyanoimino)-3-cyanoethylthiazolidine

Publications (2)

Publication Number Publication Date
JPS6051186A true JPS6051186A (en) 1985-03-22
JPH0477749B2 JPH0477749B2 (en) 1992-12-09

Family

ID=15674044

Family Applications (1)

Application Number Title Priority Date Filing Date
JP15854583A Granted JPS6051186A (en) 1983-08-30 1983-08-30 Preparation of 2-(n-cyanoimino)-3-cyanoethylthiazolidine

Country Status (1)

Country Link
JP (1) JPS6051186A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56174192U (en) * 1980-05-27 1981-12-22
JPS57897U (en) * 1980-05-29 1982-01-05
JPS63307857A (en) * 1987-06-09 1988-12-15 Nippon Tokushu Noyaku Seizo Kk Cyanoalkyl-heterocyclic compound and insecticide

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56174192U (en) * 1980-05-27 1981-12-22
JPS57897U (en) * 1980-05-29 1982-01-05
JPS6224363Y2 (en) * 1980-05-29 1987-06-22
JPS63307857A (en) * 1987-06-09 1988-12-15 Nippon Tokushu Noyaku Seizo Kk Cyanoalkyl-heterocyclic compound and insecticide

Also Published As

Publication number Publication date
JPH0477749B2 (en) 1992-12-09

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