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A method for preparing 5-arymethylene-2,4-thiazoledione derivatives catalyzed by a degradable basic ionic liquid

A basic ion, arylmethylene technology, applied in the field of organic synthesis, can solve the problems such as large consumption loss, difficult biodegradation of ionic liquids, etc., and achieves the effects of simple and convenient operation, convenient industrialized large-scale production, and cheap raw materials

Active Publication Date: 2015-10-07
日照新睿招商发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to overcome the use of alkaline ionic liquids in the prior art to catalyze the preparation of 5-aryl methylene-2,4-thiazoledione derivatives in the process of alkaline ionic liquid consumption and the loss in recycling are very large , ionic liquids are not easy to biodegrade and other shortcomings, and provide a kind of alkaline ionic liquid with high alkalinity, low preparation cost and biodegradable as a catalyst, and use water as a solvent to catalyze the preparation of 5-aryl methylene-2 , the method of 4-thiazoldione derivatives

Method used

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  • A method for preparing 5-arymethylene-2,4-thiazoledione derivatives catalyzed by a degradable basic ionic liquid
  • A method for preparing 5-arymethylene-2,4-thiazoledione derivatives catalyzed by a degradable basic ionic liquid
  • A method for preparing 5-arymethylene-2,4-thiazoledione derivatives catalyzed by a degradable basic ionic liquid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 2mmol of benzaldehyde, 2mmol of 2-thio-2,4-thiazolidinedione and 0.6mmol of degradable basic ionic liquid were added to 6ml of water in a 50ml single-necked bottle with a stirring bar and a condenser tube. Reflux reaction for 35 minutes under vigorous stirring, TLC (thin plate chromatography) detection, the raw material point disappeared, cooled to room temperature, suction filtered, and the dried filter residue was recrystallized with absolute ethanol to obtain pure 5-benzylidene-2,4- Thiazoledione 0.42g, the yield is 95%. Add benzaldehyde and 2-thio-2,4-thiazolidinedione directly to the filtrate for repeated use.

[0026] 5-benzylidene-2,4-thiazoledione: m.p.201~203℃; 1 H NMR (400MHz, CDCl 3 ): δ=7.52~7.63(m, 5H, C 6 h 5 ), 7.69 (s, 1H, CH), 13.91 (br, 1H, NH)

Embodiment 2

[0028] Add 2mmol of 2-chlorobenzaldehyde, 2mmol of 2-thio-2,4-thiazolidinedione and 0.8mmol of degradable basic ionic liquid into a 50ml single-necked bottle containing 6ml of water with a stirring bar and a condenser tube. Under vigorous stirring, reflux reaction for 52 minutes, TLC (thin plate chromatography) detection, the raw material point disappeared, cooled to room temperature, suction filtration, and the dried filter residue was recrystallized with absolute ethanol to obtain pure 5-[(2-chloro)benzylidene Base]-2,4-thiazoledione 0.48g, yield is 93%. Add 2-chlorobenzaldehyde and 2-thio-2,4-thiazolidinedione directly to the filtrate for repeated use.

[0029] 5-[(2-Chloro)benzylidene]-2,4-thiazoledione: m.p.186~188℃; 1 H NMR (400MHz, CDCl 3 ): δ=7.52~7.67(m, 4H, C 6 h 4), 7.70 (s, 1H, CH), 13.97 (br, 1H, NH)

Embodiment 3

[0031] Add 2mmol of 4-chlorobenzaldehyde, 2mmol of 2-thio-2,4-thiazolidinedione and 0.6mmol of degradable basic ionic liquid into a 50ml single-necked bottle containing 7ml of water with a stirring bar and a condenser tube. Under vigorous stirring, reflux reaction for 27 minutes, TLC (thin plate chromatography) detection, the raw material point disappeared, cooled to room temperature, suction filtration, and the dried filter residue was recrystallized with absolute ethanol to obtain pure 5-[(4-chloro)benzylidene Base]-2,4-thiazoledione 0.49g, yield is 96%. Add 4-chlorobenzaldehyde and 2-thio-2,4-thiazolidinedione directly to the filtrate for repeated use.

[0032] 5-[(4-Chloro)benzylidene]-2,4-thiazoledione: m.p.225~227℃; 1 H NMR (400MHz, CDCl 3 ): δ=7.59(s, 4H, ArH), 7.71(s, 1H, CH), 13.93(br, 1H, NH)

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Abstract

The invention provides a method for preparing a 5-arylmethylene-2, 4-thiazolidinedione derivative through the catalysis of a degradable basic ionic liquid, belonging to the technical field of organic synthesis. The molar ratio of aromatic aldehyde to 2-sulfo-2, 4-thiazolidinedione in preparation reaction is 1:1, the molar weight of a degradable basic ionic liquid catalyst is 30-50% of the molar weight of aromatic aldehyde, and the dosage (ml) of water as a reaction solvent is 3-5 times as much as the molar weight (mmol) of aromatic aldehyde. After the reaction is ended, a reactant is cooled to the room temperature, and filter residues obtained through suction filtration and drying are re-crystallized by using absolute ethyl alcohol, so that the corresponding 5-arylmethylene-2, 4-thiazolidinedione derivative is obtained. Compared with a method for preparing the 5-arylmethylene-2, 4-thiazolidinedione derivative by taking the other ionic liquid as a catalyst, the method provided by the invention is good in catalytic activity, low in catalyst dosage, relatively low in loss in recycling, green and economic in the whole reaction process, simple and convenient in operation and convenient for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for preparing 5-arymethylene-2,4-thiazoledione derivatives by catalyzing a degradable alkaline ionic liquid. Background technique [0002] 5-arymethylene-2,4-thiazoledione derivatives are a class of heterocyclic compounds with high pharmacological activity, which can be used as analgesics, fungicides, insecticides, anticancer drugs and so on. Such compounds are usually synthesized in organic solvents such as toluene, acetic acid, ethanol, DMF, and benzene, but these methods have disadvantages such as long reaction time, low yield, many side reactions, and difficult post-treatment. In addition, the use of a large amount of volatile organic solvents also brings environmental pollution. Based on this, green solvents and solvent-free preparation methods have recently appeared, but this synthesis method is also limited to a certain extent. For example,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/36
CPCC07D277/36
Inventor 岳彩波朱琳吴胜华杜勤杰陆良俊储昭莲
Owner 日照新睿招商发展有限公司