SU1525154A1 - Method of obtaining 3,3ъ-disubstituted 5-(2ъ-thionthiazolidon-4ъ-iliden-5ъ)-2-thionthiazolidons-4 - Google Patents

Abstract

This invention relates to heterocyclic compounds, in particular to the preparation of 3.3'-disubstituted 5- (2'-thionthiazolidene-4'-ylidene-5') -2-thionthiazolidon-4 of the formula @ , chlorocarbonyl lower alkyl, lower alkoxycarbonyl lower alkyl or (3-phenyl) -pyrrolidinylcarbonyl lower alkyl, which can be used in the synthesis of drugs, analysis reagents, dyes. In order to increase the yield and quality, as well as expand the range of target products, the reaction of rhodanine of the formula S-CH ₂ -C / O / -N / R ₁ / -CHS, where R _{1 is} lower alkyl, benzyl, or carboxy-lower alkyl with thionyl chloride, is carried out during boiling in CCL ₄ and, if necessary, the resulting product, where R is chlorocarbonyl lower alkyl, is subjected to subsequent treatment with water or an alcohol of the formula R ₂ OH, where R ₂ is lower alkyl or allyl, at boiling, or 3-phenylpyrrolidine at boiling in solvent. 1 tab.

Description

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The invention relates to organic chemistry, in particular to a new method of producing the known and novel 3,3-disubstituted 5- (2-thionthiazolidone-4-ylidene-5) -2-thionthiazolidone-4 derivatives, and can be used in chemical and pharmaceutical industries to produce intermediates for drug synthesis, analysis reagents, organic dyes, photosensitizers.

The purpose of the invention is to increase output and quality, as well as the expansion

product range.

This goal is achieved by the fact that the corresponding rhodanine is reacted with thionyl chloride at boiling in carbon tetrachloride and, if necessary, followed by reaction with water or alcohol at boiling or 3-fei

3

nnlpyrrolidine when boiling in a solvent,

Example 1, Preparation of 3,3-dimethyl-5- (2-thionthiazolidone-4-ylide-5) -2-thionthiazolizone-4 (compound 1).

Boil t 0.2 mol 3-methylrodanine from 0.4 mol SOClj in 90 MP CC14 5h. The precipitate is filtered hot, washed with CCl i and dried. Mass Spectra m / z 290.

Example 2. Preparation of 3,3-di benzyl-5- (2-thio-thiazolidone-4-yl-den-5) -2-thionthiazolidone-4 (compound 2).

0.2 mol of 3-benzylrodanine is dissolved in 100 ml of CC with heating, 0.4 mol of SOClj is added and the reaction mixture is boiled for 2 hours. The precipitate is hot, washed with CC1 and dried. Crystal powder red.

Example 3. Preparation of dichloro-anhydride 3, (p-carboxyethyl) -5- {2 -thio-thia-thiazolidone-4-ylidene-3) -2-thionthiazolidone-4 (compound 3).

0.1 mol of Sp-carboxyethyl-rhodanine is boiled with 0.3 mol of SOCl2 in 100 ml of CCli for 10 hours. The precipitate is filtered off.

hot, washed with CCl and dried. Crystalline powder brown.

Example 4. Preparation of 3.3-d- (B-carboxyethyl) -5- (2 -thio-thiazido lidon-4-ylidene-z) -2-thionthiazolidone-4 (compound 4).

Boil t of 20 mmol of 3,3-di- (L-carboxyethyl) -5- (2-thionthiazalidon-4-ylidene-5) - (2-thionthiazolididone-4) dichloride; and 50 ml of water for 1 h, the precipitate is filtered hot, washed with water and dried. Crystalline powder brown. Mass spectrum: m / z 406.

Example 5. Preparation of 3,3-di - ((5-carboxyethyl-5- (2-thio-thiazolidone-4-ylidene-5) -2-thionthiazolidone-4) diallyl ester) (compound 5).

Boil 2 mmoles of 3,3-di- (b-carboxyethyl) -5- (2-thionthiazolidone-4-ylidene-5) -2-thiontiazolidone-4 dichlorohydride in 10 ml of anhydrous allyl alcohol for 1 hour, precipitate filtered hot, washed with allyl alcohol, ether. Crystal powder red-orange color.

Example 6. The preparation of 3,3-di- (3-p-carboxyethyl diethyl ester

l-

44

-5 (2-thiontazolidon-4-ylidene-5) -2-thiontiazolidone-4 (compound 6).

Boil t of 2.5 mmol of 3,3-di (- carboxyethyl) -5- (2-thio-thiathazolidone-4-ylidene-5) -2-thionthia-zag1IDone-4 dichloride and 20 ml of anhydrous ethanol for 1 h, the precipitate is filtered off hot, washed with anhydrous ethanol and dried. Crystalline powder of red-orange color. Mass spectrum: m / z 462.

Example 7. Obtaining 3,3- -di- (3-phenylpyrrolid-1) -3,3- -di- ((-carboxyethyl) -5- (2 -thionolsolidon-4-ylidene-5) -2- thiontiazolidone-4 (compound 7).

To a hot solution of 20 mmol of 3,3-di- (| 3-carboxyethyl) -5- (2-thio-thiazolidon-4-ylidene-5) -2-thionthiazolidone-4-dichloride dichloride is added a solution of 30 ml of p-xylene. 40 mmol of 3-phenylpyrrolidine in 10 ml of p-xylene and boiled for 10 minutes. The reaction mixture is cooled, the precipitate is filtered off, washed with hexane and dried. Crystalline powder orange.

Constants and outputs of compounds 1-7 are given in the table.

Dimethyl and diisopropyl and dibenzyl esters of 3,3-di (p-carboxyethyl) -5- (2 - -thio-thiazolidone-4-ylidene-5) -2-thion-thiazolidone-4 (compounds 8-10) are obtained in a similar way.

Thus, the proposed method allows to improve the yield and quality of the known target products and to obtain new derivatives of the thiontiazolidone series.

Claims (1)

Invention Formula The method of obtaining 3,3-disubstituted 5- (2 -thio-tiatazolidon-4-ylidene-3-d) -2-thiontiazolidone-4 of formula R. one N-. 55 where R is lower alkyl, benzyl, allyloxycarbonyl lower alkyl, carboxy lower alkyl, chlorocarbonyl lower alkyl, lower alkoxycarbonyl lower alkyl or (3-phenyl) -pyrrolidinylcarbonyl lower alkyl. 51 due to the fact that, in terms of the yield and quality of the expansion of the range of cereals, rhodamine a common form ABOUT Lx where R is lower alkyl, benzyl or carboxy-lower alkyl, is reacted with thionyl 52515D boiling in four, carbon chloride and, if necessary, the resulting product,. where R is chlorocarbonyl alkyl, subjected to subsequent treatment with water or alcohol of the general formula , where R is lower alkyl or allyl, at boiling, or 3-phenylpyrrolidine at boiling in a solvent.