JPS6051185A - Preparation of n-cyanoiminothiazolidine derivative - Google Patents

Preparation of n-cyanoiminothiazolidine derivative

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Publication number
JPS6051185A
JPS6051185A JP15854483A JP15854483A JPS6051185A JP S6051185 A JPS6051185 A JP S6051185A JP 15854483 A JP15854483 A JP 15854483A JP 15854483 A JP15854483 A JP 15854483A JP S6051185 A JPS6051185 A JP S6051185A
Authority
JP
Japan
Prior art keywords
cyanoiminothiazolidine
formula
solvent
base
anhydride
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.)
Pending
Application number
JP15854483A
Other languages
Japanese (ja)
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 JP15854483A priority Critical patent/JPS6051185A/en
Publication of JPS6051185A publication Critical patent/JPS6051185A/en
Pending 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 a specific acid anhydride in a solvent in the presence of a base. CONSTITUTION:N-Cyanoiminothiazolidine shown by the formula I is reacted with an acid anhydride (e.g., acetic anhydride, benzoic anhydride, etc.) shown by the formula R-CO-O-CO-R (R is alkyl, or aryl) in a solvent (preferably acetone, chloroform) in the presence of a base (preferably triethylamine, or pyridine) preferably at room temperature - under reflux, to give the desired compound shown by the formula II.

Description

【発明の詳細な説明】 本発明は、下式器で示されるＮ−シアノイミノチアゾリ
ジン誘導体の製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing an N-cyanoiminothiazolidine derivative shown in the following formula.

Ｌ式中、Ｒはアルキル、またはアリールを表わす］。In the L formula, R represents alkyl or aryl].

上記化合物器は、例えばＨ２−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。The above compound is useful as a synthetic raw material for, for example, H2-receptor antagonists and anthelmintics.

本発明によれば、式［月： で示されるＮ−シアノイミノチアゾリジンと、式％式％
］ ［式中、Ｒは前記と同じ］ で示される酸無水物とを、溶媒中、触媒として塩基の存
在下に反応させることにより目的化合物器を得る。According to the present invention, an N-cyanoiminothiazolidine represented by the formula [month:
] [In the formula, R is the same as above] The target compound is obtained by reacting the acid anhydride represented by the following in a solvent in the presence of a base as a catalyst.

溶媒は、例えばアセトン、クロロホルムなどであり、塩
基としては、トリエチルアミン、ピリジンなどが好まし
く用いられる。反応は、室温ないし還流下に効率よく達
成される。The solvent is, for example, acetone, chloroform, etc., and the base is preferably triethylamine, pyridine, etc. The reaction is efficiently accomplished at room temperature to reflux.

反応液を減圧留去して残液に水を加えれば、化合物［１
１１１の結晶が得られる。これを適当な溶媒から再結晶
するか、またはクロロホルムなどの非水溶媒に再溶解し
、分液後、有機相を乾燥、濃縮することにより十分な純
品として目的化合物叫を得ることができる。If the reaction solution is distilled off under reduced pressure and water is added to the residual solution, compound [1
111 crystals are obtained. The target compound can be obtained as a sufficiently pure product by recrystallizing it from a suitable solvent or redissolving it in a nonaqueous solvent such as chloroform, separating the layers, and drying and concentrating the organic phase.

化合物［１１，ＩＪにおけるＲの例として、アルキルに
法メチル、エチル、イソプロピル、アリールには、フェ
ニル、置換フェニルが挙ケられる。Examples of R in compound [11, IJ] include methyl, ethyl, and isopropyl for alkyl, and phenyl and substituted phenyl for aryl.

実施例 ２−（Ｎ−シアノイミノ）−３−アセチルチアゾリジン
の製造： 無水酢酸５０ｍ１にＮ−シアノイミノチアゾリジン５ｙ
（０，０４モル）を懸濁させる。ついでトリエチルアミ
ン４．Ｏｆ　（０，０４モル）を加えると発熱して液が
均一になる。Example 2 - Production of (N-cyanoimino)-3-acetylthiazolidine: 5y of N-cyanoiminothiazolidine in 50ml of acetic anhydride
(0.04 mol) is suspended. Then triethylamine 4. When Of (0.04 mol) is added, heat is generated and the liquid becomes uniform.

１時間後反応液を留去して水を加えると結晶が得られる
。これをエタノールとエーテルで逐次洗浄して、２−（
Ｎ−シアノイミノ）−３−アセチルチアゾリジンを得る
。５．８ｇ（８７，２％）。融点１４３〜１４５°Ｃ。After 1 hour, the reaction solution is distilled off and water is added to obtain crystals. This was washed successively with ethanol and ether, and 2-(
N-cyanoimino)-3-acetylthiazolidine is obtained. 5.8g (87.2%). Melting point 143-145°C.

元素分析値（Ｃ６Ｈ７Ｎ３０Ｓ二１６９．２０６として
）計算値（％）：Ｃ４２，５９、Ｈ４１７、Ｎ２４．８
３実測値（％）：Ｃ４２，６２、Ｈ４，，０８、Ｎ２４
．８１゜実施例２ ２−（Ｎ−シアノイミノ）−３−ベンゾイルチアゾリジ
ンの製造： クロロホルム５０ｍ１にＮ−シア／イミノチアゾリジン
５ｇ（０，０４モル）を懸濁させる。ついでトリエチル
アミン４．０９　（０，０４モル）と無水安息香酸９ｇ
（０，０４モル）を加え一夜還流する。Elemental analysis value (as C6H7N30S2169.206) Calculated value (%): C42.59, H417, N24.8
3 Actual measurements (%): C42, 62, H4, 08, N24
．． 81° Example 2 Preparation of 2-(N-cyanoimino)-3-benzoylthiazolidine: 5 g (0.04 mol) of N-cya/iminothiazolidine are suspended in 50 ml of chloroform. Then 4.09 (0.04 mol) of triethylamine and 9 g of benzoic anhydride
(0.04 mol) and refluxed overnight.

反応液を留去し残渣に水を加えると結晶が得られる。そ
の結晶をクロロホルムに溶解し、分液後クロロホルム相
を乾燥留去して、十分純品として、２−（Ｎ−シアノイ
ミノ）−３−ベンゾイルチアゾリジンを得る。収量７．
２９（７７，８％）融点１９１〜１９３　Ｃ Ｃ目Ｈ９ＮＢＯ５＝　２３１．２７８として理論値（％
）Ｃ：５７．１８　Ｈ：３．９２　Ｎ：１８．１７実測
値（％）Ｃ：　５８．０９　Ｈ：３．８８　Ｎ：　１８
．２８０代理人　弁理士　宮　崎　新八部When the reaction solution is distilled off and water is added to the residue, crystals are obtained. The crystals are dissolved in chloroform, and after separation, the chloroform phase is dried and distilled off to obtain 2-(N-cyanoimino)-3-benzoylthiazolidine as a sufficiently pure product. Yield 7.
29 (77.8%) Melting point 191-193 C C H9NBO5 = 231.278, theoretical value (%
) C: 57.18 H: 3.92 N: 18.17 Actual value (%) C: 58.09 H: 3.88 N: 18
．． 280 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、式：％式％ 〔式中、Ｒはアルキル、またはアリールを表わす］ で示される酸無水物とを、溶媒中、塩基の存在下に反応
させて、式： 〔式中、Ｒは前記と同じ１ で示されるＮ−シアノイミノチアゾリジン誘導体の製造
法。(1) N-cyanoiminothiazolidine and an acid anhydride represented by the formula: %formula% [wherein R represents an alkyl or aryl] are reacted in a solvent in the presence of a base, : [Method for producing an N-cyanoiminothiazolidine derivative represented by the formula 1, in which R is the same as above.
JP15854483A 1983-08-30 1983-08-30 Preparation of n-cyanoiminothiazolidine derivative Pending JPS6051185A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP15854483A JPS6051185A (en) 1983-08-30 1983-08-30 Preparation of n-cyanoiminothiazolidine derivative

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP15854483A JPS6051185A (en) 1983-08-30 1983-08-30 Preparation of n-cyanoiminothiazolidine derivative

Publications (1)

Publication Number Publication Date
JPS6051185A true JPS6051185A (en) 1985-03-22

Family

ID=15674023

Family Applications (1)

Application Number Title Priority Date Filing Date
JP15854483A Pending JPS6051185A (en) 1983-08-30 1983-08-30 Preparation of n-cyanoiminothiazolidine derivative

Country Status (1)

Country Link
JP (1) JPS6051185A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61211699A (en) * 1985-03-14 1986-09-19 防衛庁技術研究本部長 Tracer-point detector

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4891064A (en) * 1972-02-08 1973-11-27
JPS5687573A (en) * 1979-12-19 1981-07-16 Mitsubishi Yuka Yakuhin Kk 2-aryl-3-acylthiazolidine derivative

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4891064A (en) * 1972-02-08 1973-11-27
JPS5687573A (en) * 1979-12-19 1981-07-16 Mitsubishi Yuka Yakuhin Kk 2-aryl-3-acylthiazolidine derivative

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61211699A (en) * 1985-03-14 1986-09-19 防衛庁技術研究本部長 Tracer-point detector

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