The synthetic method of 2-n-propyl-4-methylbenzimidazole-6-carboxylic acid

A technology of methylbenzimidazole and dimethylbenzimidazole, applied in the field of synthesis of telmisartan intermediate 2-n-propyl-4-methylbenzimidazole-6-carboxylic acid, achieving less pollution , easy to obtain raw materials, simple operation

Inactive Publication Date: 2019-12-31
HUBEI UNIV OF TECH
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Problems solved by technology

However, the catalytic carbonyl insertion reaction requires a temperature of 100 ° C, a high pressure of carbon monoxide pressure of 1.5 MPa and heavy metal palladium catalysis

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  • The synthetic method of 2-n-propyl-4-methylbenzimidazole-6-carboxylic acid
  • The synthetic method of 2-n-propyl-4-methylbenzimidazole-6-carboxylic acid

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Embodiment Construction

[0019] The synthetic method of the present invention is carried out in four steps:

[0020] In the first step, 3,5-dimethylnitrobenzene is used as raw material, nitrated by nitric acid / concentrated sulfuric acid, hydrolyzed, and filtered to generate intermediate product II 3,5-dimethyl-1,2-dinitrobenzene.

[0021] Specifically: prepare a mixed acid with 95% fuming nitric acid and 98% concentrated sulfuric acid, and store it at 0°C; add 98% concentrated sulfuric acid and 3,5-dimethylnitrobenzene into the reaction vessel, and cool it under stirring To -10°C, add dropwise the mixed acid prepared by 95% fuming nitric acid and 98% concentrated sulfuric acid, and control the feeding rate so that the reaction temperature is not higher than -5°C. After the dropwise addition, continue to stir in the ice bath for 3 hours, slowly add the reaction mixture to crushed ice for hydrolysis, keep the temperature not exceeding 5°C, and stir vigorously until a large amount of light yellow solid p...

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Abstract

The invention relates to a synthetic method of 2-n-propyl-4-methylbenzimidazole-6-carboxylic acid. The synthetic method comprises the following steps: through nitric acid / concentrated sulfuric acid nitrification reaction of 3,5-dimethylnitrobenzene, generating an intermediate product II, namely 3,5-dimethyl-1,2-dinitrobenzene; performing Pd / C catalytic hydrogenation reaction on the intermediate product II in an ethanol solution to obtain an intermediate product III, namely 3,5-dimethyl-1,2-phenylenediamine; enabling the intermediate product III to react with N-butyric acid in a polyphosphoric acid solution to obtain an intermediate product IV, namely 2-n-propyl-4,6-dimethylbenzimidazole; performing cobalt salt air liquid-phase oxidation reaction on the intermediate product IV in an acetic acid solution to obtain a product V, namely the 2-n-propyl-4-methylbenzimidazole-6-carboxylic acid. The synthetic method provided by the invention has the benefits that the operation is simple, raw materials are easy to obtain, a used solvent can be recycled, the product content can reach 95 percent or above, the yield is up to 73.2 percent, the pollution is less, and the suitability for industrial production is realized.

Description

technical field [0001] The invention belongs to the technical field of chemical pharmacy, and in particular relates to a synthesis method of telmisartan intermediate 2-n-propyl-4-methylbenzimidazole-6-carboxylic acid. Background technique [0002] Telmisartan (telmisartan), as a new type of angiotensin Ⅱ receptor antagonist antihypertensive drug, its unique new bisbenzimidazole structure ensures high receptor affinity and superior pharmacokinetic properties, At the same time, it has many advantages such as advanced mechanism of action, stable blood pressure reduction, no rebound, long-acting and high-efficiency, good tolerance, targeted selection, small side effects, good adaptability, etc. Hypertensive patients have good curative effect. [0003] Over the past 20 years, domestic and foreign scholars have done a lot of research on the production process and technology of telmisartan, and proposed many new processes and technologies, mainly using toluene derivatives and benz...

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/08
CPCC07D235/08
Inventor 徐保明张克陈坤胡传群唐强毛仁群许庆博徐思思时爽张家辉张弘李俊李志鹏
Owner HUBEI UNIV OF TECH
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