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Method for catalytic synthesis of benzimidazole derivatives

A technology for benzimidazole derivatives and derivatives, which is applied in the field of catalytic synthesis of benzimidazole derivatives, can solve the problems of large usage and loss, complicated preparation process, difficult biodegradation, etc. Simple, inexpensive ingredients

Active Publication Date: 2015-05-13
平邑现代中药产业园有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to overcome the disadvantages of the prior art in the catalytic preparation of benzimidazole derivatives, such as large usage and loss of acidic ionic liquid, high preparation cost, complicated preparation process and difficult biodegradation, and provide a A degradable acidic ionic liquid that is relatively cheap to prepare, easy to biodegrade, has a small amount of loss during use, and can simplify the operation process is used as a catalyst to catalyze the preparation of benzimidazole derivatives under the condition of using a mixture of water and ethanol as a solvent. Methods

Method used

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  • Method for catalytic synthesis of benzimidazole derivatives
  • Method for catalytic synthesis of benzimidazole derivatives
  • Method for catalytic synthesis of benzimidazole derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Add 1mmol of benzaldehyde, 1mmol of o-phenylenediamine and 0.03mmol of degradable acidic ionic liquid catalyst to 4ml of water and ethanol mixture (V (water): V (ethanol)=1:1) with stirring Stir vigorously at room temperature for 7 minutes, followed by TLC (thin plate chromatography) detection. After the reaction, a large amount of solids precipitate out, crush the solids, let stand, and filter with suction. The resulting filter residue is vacuum-dried to obtain pure 2-benzene Base-1H-benzimidazole with a yield of 98%. The filtrate was directly added with benzaldehyde and o-phenylenediamine for repeated use.

[0024] 2-Phenyl-1H-benzimidazole: m.p.285~287℃; 1 H NMR (400MHz, DMSO-d 6 ): δ=7.18~7.27(m, 2H), 7.45~7.56(m, 4H), 7.66~7.77(m, 1H), 8.15~8.23(m, 2H), 12.94(s, 1H)

Embodiment 2

[0026] Add 1mmol of p-chlorobenzaldehyde, 1mmol of o-phenylenediamine and 0.04mmol of degradable acidic ionic liquid catalyst to the belt containing 5ml of water and ethanol mixture (V (water): V (ethanol) = 1:1). In a 25ml single-necked bottle with a stirrer, stir vigorously at room temperature for 8 minutes, TLC (thin-plate chromatography) tracking detection, after the reaction is completed, a large amount of solids are precipitated, crushed solids, left standing, and suction filtered, and the obtained filter residue is vacuum-dried to obtain pure 2 -(4-Chlorophenyl)-1H-benzimidazole, the yield was 98%. After directly adding p-chlorobenzaldehyde and o-phenylenediamine in the filtrate, it is reused.

[0027] 2-(4-Chlorophenyl)-1H-benzimidazole: m.p.291~292℃; 1 H NMR (400MHz, DMSO-d 6 ): δ=7.12~7.31(m, 2H), 7.46~7.73(m, 4H), 8.17(d, J=8.6Hz, 2H), 12.98(s, 1H)

Embodiment 3

[0029]Add 1mmol of m-nitrobenzaldehyde, 1mmol of o-phenylenediamine and 0.05mmol of degradable acidic ionic liquid catalyst to the tank containing 5ml of water and ethanol mixed solution (V (water): V (ethanol) = 1:1). In a 25ml single-necked bottle with a stirrer, stir vigorously at room temperature for 26min, TLC (thin plate chromatography) tracking detection, after the completion of the reaction, a large amount of solids precipitate out, crush the solids, stand still, and suction filter, the obtained filter residue is vacuum-dried to obtain pure 2-(3-nitrophenyl)-1H-benzimidazole, yield 97%. After directly adding m-nitrobenzaldehyde and o-phenylenediamine in the filtrate, it is reused.

[0030] 2-(3-nitrophenyl)-1H-benzimidazole: m.p.213~214℃; 1 H NMR (400MHz, DMSO-d 6 ): δ=7.29(s, 2H), 7.61(d, J=6.0Hz, 1H), 7.74(d, J=6.9Hz, 1H), 7.87(t, J=8.0Hz, 1H), 8.60~8.65 (m, 1H), 9.02~9.06(m, 1H), 13.28(s, 1H)

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Abstract

The invention discloses a method for catalytic synthesis of benzimidazole derivatives and belongs to the field of organic chemical synthesis. In the synthesis reaction, the molar ratio of aromatic aldehyde to o-phenylenediamine is 1: 1, the molar amount of biodegradable acidic ionic liquid catalyst is 3-5% of the use amount of aromatic aldehyde, the reaction time at room temperature is 7-30min, the volume of a reaction solvent, namely, a mixed solution of water and ethanol, is 4-6 times the molar amount of aromatic aldehyde, the reaction pressure is one atmospheric pressure, the suction filtration is performed after the reaction is completed, and obtained filter residue is dried in vacuum to obtain the pure benzimidazole derivatives. Compared with other preparation method, the method disclosed by the invention has the characteristics that the preparation process is simple, raw materials are relatively cheap, better biodegradability is achieved, the loss is low during the recycling process, the entire preparation process is environmental friendly and is simple and convenient to operate, and the industrial large-scale production is facilitated.

Description

technical field [0001] The invention belongs to the technical field of chemical material preparation, and in particular relates to a method for catalytically synthesizing benzimidazole derivatives. Background technique [0002] Benzimidazole derivatives are benzoheterocyclic compounds containing two nitrogen atoms, which have a variety of biological activities, such as antihypertensive, antiparasitic, anticancer, antibacterial, plant growth regulation, etc., and can be used as drug intermediates It is an important class of active substances in the fields of medicine and pesticides, which is of great significance; on the other hand, it also shows special and excellent performance in many fields such as materials and catalysis. Therefore, the synthesis of benzimidazole derivatives has been widely concerned. The traditional method for synthesizing benzimidazole derivatives is to use o-phenylenediamine compounds as raw materials and then condense them with aldehydes and carboxy...

Claims

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Application Information

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IPC IPC(8): C07D235/18B01J31/02
CPCC07D235/18
Inventor 岳彩波胡慧慧吴胜华郭涛张欣杨翠萍储昭莲
Owner 平邑现代中药产业园有限公司
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