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Industrialized preparation method of using 2-bromothiazole for compounding thiazole-2-methanamide in a one-boiler mode

A technology of bromothiazole and formamide, which is applied in the field of industrial preparation, can solve the problems of high raw material cost, safety, and low yield, and achieve the effects of low preparation cost, easy reaction control, and simple process

Active Publication Date: 2012-06-27
上海药明康德新药开发有限公司 +1
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Problems solved by technology

[0021] The technical problem to be solved in the present invention is: solving the problems of high cost of raw materials in the existing thiazole-2-carboxamide preparation process, potential safety hazards in large-scale production, and low yield; providing a low-cost, high-yield Higher, safe one-pot synthesis of thiazole-2-carboxamides for industrial production

Method used

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  • Industrialized preparation method of using 2-bromothiazole for compounding thiazole-2-methanamide in a one-boiler mode
  • Industrialized preparation method of using 2-bromothiazole for compounding thiazole-2-methanamide in a one-boiler mode
  • Industrialized preparation method of using 2-bromothiazole for compounding thiazole-2-methanamide in a one-boiler mode

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Embodiment 1

[0034] 1000 mL of methyl tert-butyl ether was added to a 3 L three-necked flask, stirred, cooled to -75° C., and 220 mL of n-butyllithium in n-hexane solution (2.5 mol / L) was added. A solution of 2-bromothiazole (82.01 g) in methyl tert-butyl ether (500 mL) was added dropwise, the temperature was controlled at -70°C to -75°C, and stirring was continued for 0.5 hours after the dropwise addition was completed.

[0035] Dry carbon dioxide gas was introduced into the above obtained mixture, and the temperature was controlled at -70°C to -75°C until the reaction was completed. The temperature was slowly raised to 25° C. and concentrated to dryness to obtain 76 g of solid, namely lithium thiazole-2-carboxylate, the weight content of which was 65.2%, and the yield was 73.4%.

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Abstract

The invention relates to an industrialized preparation method of using 2-bromothiazole for compounding thiazole-2-methanamide in a one-boiler mode, which uses cheap and easily-obtained 2-bromothiazoleas a raw material to obtain thiazole-2-methanamide after carbonyl-inserting reaction, chlorination and ammonolysis. The reaction formula is as below. The invention solves the problems of environmental pollution, safety danger in production, high cost, low yield, and the like in the prior art, the intermediate product is not required to be purified, the target product can be obtained in one step, the operation is simple, and the large-scale industrialized production can be realized.

Description

Technical field: [0001] The invention relates to an industrialized preparation method for synthesizing thiazole-2-carboxamide by one-pot method from 2-bromothiazole. Background technique: [0002] Thiazole-2-carboxamide is an important pharmaceutical intermediate, but so far there is no effective industrial synthesis method for the preparation of this product. [0003] Two methods for the preparation of thiazole-2-carboxamides have been reported in the literature. [0004] In the first method, thiazole-2-carboxylic acid is used as a raw material, and the carboxyl group is activated under the action of C1COOEt, and then thiazole-2-carboxamide is prepared by ammonia water. (Acta Chem. Scand.; 21; 1967; 389-396.) [0005] Literature synthesis route: [0006] [0007] The reason why this method is not suitable for industrial production is: the raw material thiazole-2-carboxylic acid is expensive and the production cost is high; the use of ethyl chloroformate, which is more...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/56
Inventor 尤旭东杨成武何大荣周盛峰郭劲松顾虹唐苏翰李革
Owner 上海药明康德新药开发有限公司
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