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Method for preparing 2,4-thiazolidinedione

A technology of thiazolidinedione and thiazolidinedione, which is applied in the field of preparation of pharmaceutical intermediates, can solve the problems of low yield, difficult recrystallization, poor product purity and the like, and achieves simple operation, easy recrystallization and easy control of conditions. Effect

Active Publication Date: 2014-02-05
SHANDONG JINCHENG PHARMACEUTICAL GROUP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The purpose of the present invention is to provide a high-purity, high-yield 2,4-thiazolidinedione preparation method to overcome the problems of poor product purity, low yield, and difficult recrystallization that are ubiquitous in the prior art.

Method used

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  • Method for preparing 2,4-thiazolidinedione

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Embodiment 1

[0024] Add 800kg of water to the drying reactor, turn on the stirring, add 100kg of sulfuric acid, and then add 410kg of chloroacetic acid. Stir for 15min. After complete dissolution, add 300kg of thiourea, start to heat up to about 102°C, and keep warm for 3 hours. After the reaction, take a sample point plate for inspection. After the reaction is complete, cool down to 19°C, discharge, filter, and weigh.

[0025] After adding water, add the crude product for refining. Raise the temperature to about 80°C until completely dissolved. Perform hot filtration. Then cool down and crystallize to 15°C, and filter by centrifugation.

[0026] After inspection: the product has a purity of 99.9%, a yield of 90%, and a pH of 2. Pack and seal after drying.

Embodiment 2

[0028] Add 400kg of water to the drying reactor, turn on the stirring, add 50kg of sulfuric acid, and then add 205kg of chloroacetic acid. Stir for 15min. After complete dissolution, add 150 kg of thiourea, start to heat up to about 95°C, and keep warm for 4 hours. After the reaction, take a sample and spot the plate for detection. The developing agent is n-hexane: ethyl acetate = 1:1. After the reaction is complete, The temperature was lowered to 15°C, and solid 2,4-thiazolidinedione was precipitated, which was discharged, filtered, and weighed.

[0029] After adding water, add the crude product for refining. Raise the temperature to about 80°C until completely dissolved. Perform hot filtration. Then cool down and crystallize to 19°C, and filter by centrifugation.

[0030] After inspection: the product 2,4-thiazolidinedione has a purity of 99.8%, a yield of 87%, a pH of 3, and is packaged and sealed after drying.

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Abstract

The invention in particular relates to a method for preparing 2,4-thiazolidinedione. The method comprises the following steps: (1) dissolving chloroacetic acid into an aqueous solution with the pH value of 0.5 to 2, adding thiourea, controlling the pH value to be 0.5 to 2, keeping the temperature and reacting, performing sampling point plate detection, after the reaction is accomplished, and cooling down so as to separate out a crude thiazole diketone product; (2) dissolving the crude thiazole diketone product into water, performing thermal filtration, cooling down, crystallizing, growing crystal, and filtering so as to obtain high-purity 2,4-thiazolidinedione crystal. The method is short in synthesis method, simple to operate, easy to control the condition, easy to recrystalize, high in yield and high in product purity, and has certain reference values for industrial production.

Description

technical field [0001] The present invention relates to a preparation method of a pharmaceutical intermediate, in particular to a preparation method of 2,4-thiazolidinedione. Background technique [0002] Thiazolidinedione drugs (TZDs) are a new class of drugs that increase insulin sensitivity. Its development has gone through two generations. The first-generation drug troglitazone has been eliminated due to its liver toxicity; The second generation mainly includes rosiglitazone and pioglitazone. TZDs can not only effectively protect the function of islet cells and improve blood sugar, but also have cardiovascular protection and good safety. [0003] Thiazolidinedione (rIZD) insulin sensitizers have achieved great success in clinical practice, and have been marketed abroad as a new generation of oral and powerful diabetes treatment drugs, and research on such drugs has also begun in China. The typical feature of non-insulin-dependent diabetes mellitus (NIDDM) is that the s...

Claims

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Application Information

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IPC IPC(8): C07D277/34
CPCC07D277/34
Inventor 侯乐伟房正薇孙智源蔡会敏赵奇李珊珊
Owner SHANDONG JINCHENG PHARMACEUTICAL GROUP CO LTD