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A production process for 2-n-propyl-4-methyl-6-(1-methylbenzimidazole-2-yl)benzimidazole

A technology of methyl benzimidazole and benzimidazole, applied in directions such as organic chemistry, can solve problems such as high cost, high consumption, poor effect, etc., and achieve the effects of rapid synthesis, high yield and cost reduction

Active Publication Date: 2015-04-29
开封缘润药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The color of the intermediate of bis-imidazole will have a major impact on the subsequent production. In addition, in the various production links of the project, there are constantly discolored substances, especially in the synthesis of 2-n-propyl-4-methyl-6 (1- In the case of methylbenzimidazol-2-yl)-benzimidazole, in order not to involve patent issues, N-methyl o-phenylenediamine hydrochloride was used as a synthetic raw material in China, so how the color can meet the requirements has also become a problem for many manufacturers. Manufacturers have a headache. The method of solvent washing and recrystallization is generally used. This method is costly, consumes a lot, and has poor results.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The production technology of 2-n-propyl-4-methyl-6 (1-methylbenzimidazol-2-yl)-benzimidazole comprises the following steps:

[0027] Intermediate b and intermediate c are dehydrated and ring-closed in polyphosphoric acid at 145°C, then subjected to water analysis, alkalized with 30% liquid alkali by mass, extracted with isopropanol, and finally precipitated Crystallization to obtain 2-n-propyl-4-methyl-6(1-methylbenzimidazol-2-yl)-benzimidazole;

[0028] The preparation steps of intermediate b:

[0029] a. Reduction step: the intermediate a is dissolved in methanol, reduced by adding hydrogen at 0.2mpa pressure and 75°C, and then precipitated to obtain methyl 3-methyl-4-butyrylamide-5-aminobenzoate;

[0030] b. Cyclization step: the 3-methyl-4-butyrylamide-5-aminobenzoic acid methyl ester obtained in the above reduction step is dissolved in toluene, then p-toluenesulfonic acid is added, and dehydrated at 105°C under reflux Cyclization into 2-n-propyl-4-methylbenzimida...

Embodiment 2

[0043] The production technology of 2-n-propyl-4-methyl-6 (1-methylbenzimidazol-2-yl)-benzimidazole comprises the following steps:

[0044] Intermediate b and intermediate c are dehydrated and ring-closed in polyphosphoric acid at 150°C, followed by water analysis, basified with 30% liquid alkali by mass, extracted with isopropanol, and finally precipitated Crystallization to obtain 2-n-propyl-4-methyl-6(1-methylbenzimidazol-2-yl)-benzimidazole;

[0045] The preparation steps of intermediate b:

[0046] a. Reduction step: intermediate a is dissolved in methanol, reduced by adding hydrogen at 0.3mpa pressure and 80°C, and then precipitated to obtain 3-methyl-4-butyrylamino-5-aminobenzoic acid methyl ester;

[0047] b. Cyclization step: the 3-methyl-4-butanylamino-5-aminobenzoic acid methyl ester obtained in the above reduction step is dissolved in toluene, then p-toluenesulfonic acid is added, and dehydrated under reflux at 110°C Cyclization into 2-n-propyl-4-methylbenzimidaz...

Embodiment 3

[0060] The production technology of 2-n-propyl-4-methyl-6 (1-methylbenzimidazol-2-yl)-benzimidazole comprises the following steps:

[0061] Intermediate b and intermediate c are dehydrated and ring-closed in polyphosphoric acid at 155°C, followed by water analysis, basified with 30% liquid alkali by mass, extracted with isopropanol, and finally precipitated Crystallization to obtain 2-n-propyl-4-methyl-6(1-methylbenzimidazol-2-yl)-benzimidazole;

[0062] The preparation steps of intermediate b:

[0063] a. Reduction step: the intermediate a is dissolved in methanol, reduced by adding hydrogen at 0.4mpa pressure and 85°C, and then precipitated to obtain 3-methyl-4-butyrylamino-5-aminobenzoic acid methyl ester;

[0064] b. Cyclization step: the 3-methyl-4-butanylamino-5-aminobenzoic acid methyl ester obtained in the above reduction step is dissolved in toluene, then p-toluenesulfonic acid is added, and dehydrated under reflux at 115°C Cyclization into 2-n-propyl-4-methylbenzim...

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Abstract

The invention relates to a production process for 2-n-propyl-4-methyl-6-(1-methylbenzimidazole-2-yl)benzimidazole. The production process comprises steps of subjecting an intermediate b and an intermediate c to a dehydration cyclization reaction in polyphosphoric acid at a temperature of 145-155 DEG C; elutriating, alkalizing by using a caustic soda liquid having a concentration of 30 m%, and extracting by using isopropanol; and removing solvent and crystallizing to obtain 2-n-propyl-4-methyl-6-(1-methylbenzimidazole-2-yl)benzimidazole. The production process has advantages of simple process, rapid synthesis, mild reaction conditions, easily available raw materials, reduced cost, high yield, reduced waste acid and gas discharges, and reduced non-acid waste water discharges.

Description

technical field [0001] The invention relates to a production process of 2-n-propyl-4-methyl-6(1-methylbenzimidazol-2-yl)-benzimidazole, which belongs to the field of chemical industry. Background technique [0002] Benzimidazole compounds have a wide range of biological activities, such as anti-cancer, anti-fungal, anti-inflammatory, etc. They are used as new curing agents for epoxy resins, catalysts, and surface treatment agents for certain metals. They can also be used as intermediates in organic synthesis reactions, etc. . [0003] Many synthesis methods have been reported, mainly through the condensation reaction of o-phenylenediamine, carboxylic acid and their derivatives under conditions such as strong acid. Carboxylic acid and lipid are usually prepared from aldehydes, which require a long route and a long reaction time, requiring special catalysts and Solvent, few sources of raw materials. [0004] The color of the intermediate of bis-imidazole will have a major im...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/20
Inventor 王力倪协屏孙乐达黄达张少伟
Owner 开封缘润药业有限公司