Benzimidazole and its derivative synthetic method

A benzimidazole and material technology, applied in the field of synthesizing benzimidazole and its derivatives, can solve the problems of phosphoric acid and polyphosphoric acid systems polluting the environment, consuming acid and alkali, and poor catalytic effect, achieving high yield and protection environment, easy-to-achieve effects

Inactive Publication Date: 2003-11-12
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the hydrochloric acid catalyst cannot obtain the corresponding benzimidazole product for the reaction of carboxylic acid with high boiling point and o-phenylenediamine, the catalytic effect of phosphoric acid is relatively poor, and the catalytic effect of polyphosphoric acid is better, but phosphoric acid and polyphosphoric acid system poll

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Synthesis of 2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazole

[0023] In a 100ml three-neck flask equipped with a reflux tube and an electromagnetic stirring device, add 50ml 1,2-propanediol, 0.05mol N-methyl o-phenylenediamine, 0.05mol 2-n-propyl-4-methyl-6- Carboxybenzimidazole, in N 2 Under gas protection, stirred and refluxed for 20 hours, the reaction solution was dark green at first, and then turned orange-yellow. After the reaction, 1,2-propanediol was evaporated under reduced pressure, and the residue was dissolved in 80ml of ethanol, decolorized by activated carbon, filtered, and the filtrate poured into 400ml of distilled water, a white solid was precipitated, suction filtered, washed with water, dried, and recrystallized with 60% ethanol to obtain a white crystal 2-n-propyl-4-methyl-6-(1-methylbenzimidazole- 2-yl)benzimidazole, yield 76%, melting point 132-134°C. Mass spectrum (m / Z): 303 (M, base peak). nuclear magnetic resonance 1 H NMR (δ...

Embodiment 2

[0025] Synthesis of 2-n-Propylbenzimidazole

[0026] In a 100ml three-necked flask equipped with a reflux tube and an electromagnetic stirring device, add 50ml of 1,2-propanediol, 0.05mol of o-phenylenediamine, and 0.05mol of n-butyric acid. 2Under gas protection, stirred and refluxed for 14 hours, the reaction solution was pink. After the reaction, 1,2-propanediol was evaporated under reduced pressure, and the residue was dissolved in 50ml of ethanol, decolorized by activated carbon, filtered, and the filtrate was poured into 150ml of distilled water to precipitate white The solid was suction filtered, washed with water, dried, and recrystallized with 60% ethanol to obtain white crystals of 2-n-propylbenzimidazole with a yield of 88% and a melting point of 162-163°C. Mass spectrum (m / Z): 160 (M, base peak). nuclear magnetic resonance 1 H NMR (δ, DMSO): 0.94 (t, 3H), 1.78 (m, 2H), 2.50 (t, 2H), 7.11 (m, 2H), 7.45 (m, 2H), 12.18 (yes, H). IR (cm -1 ): 3083~2627 (broad peak)...

Embodiment 3

[0028] Synthesis of 2-Trifluoromethylbenzimidazole

[0029] In a 100ml three-necked flask equipped with a reflux tube and an electromagnetic stirring device, add 50ml 1,3-propanediol, 0.05mol o-phenylenediamine, 0.05mol trifluoroacetic acid, and 2 Under air protection, stirred and reacted at 70°C for 10h, the reaction solution was a colorless transparent solution, after the reaction, cooled, added 100ml of cold distilled water, a white solid was precipitated, washed with water, dried, and recrystallized with 60% ethanol to obtain a white crystal 2 - Trifluoromethylbenzimidazole 7.44 g, yield 80%, melting point: 208-210°C. Mass spectrum (m / Z): 186 (M, base peak). nuclear magnetic resonance 1 H NMR (δ, DMSO): 8.2 (s, 1H), 7.7 (m, 2H), 7.4 (m, 2H).

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Abstract

The method for preparing benzimidazole and its derivative is characterized by that it uses o-phenylenediamine and its derivative and organic carboxylic acid as raw material, uses the alcohol substances of 1,2-propanediol, etc. as solvent of reaction system and cyclization catalyst, under the condition of a certain temp. makes them produce reaction to prepare the invented product. Said method is applicable to general organic carboxylic acid, and the 1,2-propanediol and other alcohol substances can be recovered and circularly used.

Description

technical field [0001] The invention relates to a method for synthesizing benzimidazole and its derivatives using 1,2-propanediol and other alcohols with a boiling point greater than 150°C as reaction catalysts and solvent systems, o-phenylenediamine and its derivatives, and organic carboxylic acids. The invention belongs to a new synthesis method in the field of chemical industry. Background technique [0002] Benzimidazoles Benzimidazole heterocyclic compounds have a wide range of biological activities such as anticancer, antifungal, treatment of hypoglycemia and physiological disorders and so on. Benzimidazole derivatives are also widely used as ligands in radiopharmaceuticals, and have high anti-inflammatory activity. For the reaction of preparing benzimidazoles from o-phenylenediamine and its derivatives, organic carboxylic acids and carboxylic acid derivatives, the commonly used catalysts are: hydrochloric acid [c(HCl)=4mol / L], phosphoric acid, poly Polyphosphoric ac...

Claims

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Application Information

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IPC IPC(8): C07D235/08
Inventor 周智明余伟发章军余从煊
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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