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: 2009-10-07
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] Add 1000mL of methyl tert-butyl ether into a 3L three-necked flask, stir, cool to -75°C, and add 220mL of n-butyl lithium in n-hexane (2.5mol / L). 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] Pass dry carbon dioxide gas into the mixture obtained above, and control the temperature at -70°C to -75°C until the reaction is complete. Slowly raise the temperature to 25°C and concentrate to dryness to obtain 76g of solid, namely lithium thiazole-2-carboxylate, with a weight content of 65.2% and a yield of 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-bromothiazole as a raw material to obtain thiazole-2-methanamide after carbonyl-inserting reaction, chlorination and ammonolysis. The reaction formula is as above. 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 industrial preparation method for synthesizing thiazole-2-carboxamide from 2-bromothiazole in one pot. Background technique: [0002] Thiazole-2-carboxamide is an important pharmaceutical intermediate, but so far there is no effective industrial synthesis method for preparing this product. [0003] Two methods for the preparation of thiazole-2-carboxamides have been reported in the literature. [0004] Method 1, thiazole-2-carboxylic acid is used as a raw material, the carboxyl group is activated under the action of ClCOOEt, 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 that: the raw material thiazole-2-carboxylic acid is expensive and the production cost is high; the highly toxic ethyl chloroformate is used, which is not conducive to env...

Claims

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Application Information

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Patent Type & Authority Applications(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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