Synthesis method of 5-methyl-2-aminothiazole

The technology of an aminothiazole and a synthesis method, which is applied in the direction of organic chemistry and the like, can solve the problems of harsh preparation conditions of 2-chloropropionaldehyde, difficult separation and purification, and high requirements for production conditions, and achieves low cost of raw materials, stable intermediates, and high raw materials. easy-to-get effect

Pending Publication Date: 2022-03-18
天象生物药业邢台有限责任公司
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Problems solved by technology

[0004] 5-Methyl-2-aminothiazole is an important intermediate for the synthesis of meloxicam. The synthetic method reported in the literature is mainly through the reaction of thiourea and 2-halopropanal, but the preparation of 2-chloropropanal Harsh conditions, difficult separation and purification, and easy to be oxidized, high requirements for production conditions, difficult to scale up production

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  • Synthesis method of 5-methyl-2-aminothiazole
  • Synthesis method of 5-methyl-2-aminothiazole

Examples

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Embodiment 1

[0032] Dissolve 12.3g of methyl 2-chloropropionate and 8.0g of thiourea in 100mL of DMF, slowly heat to 80°C, keep for 5 hours, then cool down to room temperature, add 100mL of distilled water, a bright yellow precipitate precipitates, filter, and 20mL of ice water Wash the filter cake, place the filter cake in an oven, and dry it at 60° C. to constant weight to obtain 12.1 g of bright yellow powder 5-methyl-2-amino-4(5H)thiazolone (I), with a yield of 93%.

Embodiment 2

[0034] Dissolve 12.3g of methyl 2-chloropropionate and 8.0g of thiourea in 100mL of DMF, cool to 0°C, keep for 5 hours, add 100mL of distilled water, precipitate a bright yellow precipitate, filter, wash the filter cake with 20mL of ice water, and The filter cake was placed in an oven and dried at 60°C until constant weight to obtain 10.9 g of bright yellow powder with a yield of 83%.

Embodiment 3

[0036] Dissolve 12.3g of methyl 2-chloropropionate and 11.5g of thiourea in 100mL of DMF, slowly heat to 100°C, keep for 5 hours, then cool down to room temperature, add 100mL of distilled water, a bright yellow precipitate precipitates, filter, 20mL of ice water Wash the filter cake, place the filter cake in an oven, and dry at 60°C until constant weight to obtain 10.2 g of bright yellow powder 5-methyl-2-amino-4(5H)thiazolone (I), with a yield of 76.9%.

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Abstract

The invention relates to the technical field of synthesis of drug intermediates, and provides a synthesis method of 5-methyl-2-aminothiazole, which comprises the following steps: S1, reacting 2-halogenated alkyl propionate with thiourea in an organic solvent system to prepare an intermediate I; s2, the intermediate I is subjected to a chlorination reaction, and an intermediate II is obtained; s3, the intermediate II is subjected to hydrogenation catalysis through a catalyst, and 5-methyl-2-aminothiazole is obtained. According to the technical scheme, the problems that a synthesis method in the prior art is high in separation and purification difficulty, and production is not easy to amplify are solved.

Description

technical field [0001] The invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to a synthesis method of 5-methyl-2-aminothiazole. Background technique [0002] Meloxicam is an enol nonsteroidal anti-inflammatory drug with anti-inflammatory, analgesic and antipyretic effects. Selectively inhibits cyclooxygenase-2 (COX-2), and has a weak inhibitory effect on cyclooxygenase-1, so there are few adverse reactions such as the digestive system. [0003] [0004] 5-Methyl-2-aminothiazole is an important intermediate for the synthesis of meloxicam. The synthetic method reported in the literature is mainly through the reaction of thiourea and 2-halopropanal, but the preparation of 2-chloropropanal The conditions are harsh, separation and purification are difficult, and it is easy to be oxidized. It requires high production conditions and is not easy to scale up production. Contents of the invention [0005] The present invention ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/40
CPCC07D277/40
Inventor 于秀芹李林郭军臣梅玉龙
Owner 天象生物药业邢台有限责任公司
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