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1,2-disubstituted benzimidazole compound preparation method

A technology of benzimidazole and aldehyde compounds, which is applied in the field of preparation of benzimidazole compounds, can solve the problems of unsuitable recovery of catalysts, limited scope of application, increase of dangerous types, etc., and achieve high raw material utilization, convenient operation, and reaction The effect of mild conditions

Inactive Publication Date: 2013-12-11
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still many defects in this preparation method: if some need to add an oxidizing agent, which increases the risk of operation, some use expensive catalysts that are not suitable for recovery, some have low selectivity, and the scope of application is not wide, thus limiting its use. applicability

Method used

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  • 1,2-disubstituted benzimidazole compound preparation method
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  • 1,2-disubstituted benzimidazole compound preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: Compound (I-1)

[0022] O-phenylenediamine (0.1080g, 1mmol), benzaldehyde (233.5ul, 2.2mmol), nano-zinc oxide (purchased from Aladdin Reagent Company, particle size 30±10nm) (0.0082g, 0.1mmol) in 1, Mixed with 1,2,2-tetrachloroethane (2 mL), stirred in an oil bath at 60°C for reaction, followed by TLC, and the reaction was complete in 1 hour. After the reaction, extract with ethyl acetate (10mL×3), wash with saturated brine, combine the organic phases, dry over anhydrous sodium sulfate, filter, concentrate, the concentrate is separated by column chromatography, and the volume of petroleum ether and ethyl acetate Ratio = 8:1 mixed solvent as eluent, collect R f The eluate with a value of 0.3-0.35 was evaporated under reduced pressure to remove the solvent, and dried to obtain 0.2095 g of the target compound (I-1), with a yield of 73.7%.

[0023]

[0024] 1 H NMR (500MHz, CDCl 3 ):δ7.91(d,J=7.9Hz,1H),7.76–7.67(m,2H),7.51–7.46(m,3H),7.38–7.31(m,4H),7.27–7...

Embodiment 2

[0026] Change the solvent to CHCl 3 (0.5ml), other operation is with embodiment 1, and yield is 74.4%.

Embodiment 3

[0028] The solvent was replaced with water, the reaction time was 1.5h, other operations were the same as in Example 1, and the yield was 67.3%.

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Abstract

The present invention discloses a preparation method of a 1,2-disubstituted benzimidazole compound represented by a formula (I). The preparation method comprises: mixing an aldehyde compound represented by a formula (II) and o-phenylene diamine represented by a formula (III), carrying out a stirring reaction in an inert organic solvent or water at a temperature of 10-150 DEG C under a nanometer zinc oxide catalyst effect, carrying out TLC tracking detection until the reaction is completed, and carrying out a post-treatment on the reaction solution after completing the reaction to obtain the 1,2-disubstituted benzimidazole compound represented by the formula (I). According to the present invention, nanometer zinc oxide is adopted as the catalyst, reaction conditions are mild, operations are convenient, and a yield is high.

Description

(1) Technical field [0001] The invention relates to a preparation method of 1,2-substituted benzimidazole compounds. (2) Background technology [0002] Benzimidazole ring compounds have various biological activities such as anti-HIV-1, anti-tumor, anti-cell proliferation, anti-parasite, anti-inflammation, anti-oxidation and anti-epileptic. The traditional synthesis method of 1,2-substituted benzimidazoles is mainly prepared by the dehydration ring-closure reaction of two molecules of aldehydes and o-phenylenediamine. However, there are still many defects in this preparation method: if some need to add an oxidizing agent, which increases the risk of operation, some use expensive catalysts that are not suitable for recovery, some have low selectivity, and the scope of application is not wide, thus limiting its use. applicability. (3) Contents of the invention [0003] The purpose of the present invention is to improve the defects of the prior art, and provide a catalyst th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/18C07D235/08
Inventor 崔冬梅朱观明张辰
Owner ZHEJIANG UNIV OF TECH
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