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Preparation method of α-cyanoaryl vinyl benzimidazole

A technology of vinylbenzimidazole and cyanomethylbenzimidazole is applied in the field of preparation of α-cyanoarylvinylbenzimidazole, which can solve the problems of long time consumption, harsh reaction conditions, cumbersome post-processing and the like, and achieves The effect of convenient post-processing, few side reactions and wide application range

Active Publication Date: 2021-07-20
HUAIYIN TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] This method needs to be catalyzed by a strong base, and the reaction conditions are harsh and time-consuming
After the reaction is over, the reaction system needs to be neutralized to neutral, and the post-treatment is cumbersome
At the same time, due to the use of basic catalysts, it is not suitable for the preparation of products containing alkali-sensitive functional groups

Method used

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  • Preparation method of α-cyanoaryl vinyl benzimidazole
  • Preparation method of α-cyanoaryl vinyl benzimidazole
  • Preparation method of α-cyanoaryl vinyl benzimidazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Step 1) Add 2-cyanomethylbenzimidazole (1.0mmol), 3,5-dimethoxybenzaldehyde (1.0mmol), carbon tetrabromide (0.1mmol) and absolute ethanol in a 25mL round bottom flask 2mL, react under reflux for 10 minutes;

[0019] Step 2) After the reaction is completed, cool to room temperature, a large amount of product precipitates, filter with suction, and wash the crude product with ethanol to obtain the pure product 2-(1H-benzo[d]imidazole)-3-(3,5-dimethoxy Phenyl)-acrylonitrile,

[0020]

[0021] Yield: 74%; Pale yellow solid; H NMR spectrum (DMSO-d 6 , 400MHz) (δ, ppm): 13.09(s, 1H), 8.28(s, 1H), 7.70(d, J=8.0Hz, 1H), 7.56(d, J=8.0Hz, 1H), 7.29-7.24 (m, 2H), 7.17 (d, J=2.0Hz, 2H), 6.74 (s, 1H), 3.83 (s, 6H).

Embodiment 2

[0023] Step 1) add 2-cyanomethylbenzimidazole (1.0mmol), 4-methylbenzaldehyde (1.0mmol), carbon tetrabromide (0.1mmol) and absolute ethanol 2mL in 25mL round bottom flask, under reflux Under the conditions, react for 9 minutes;

[0024] Step 2) After the reaction is finished, cool to room temperature, a large amount of product is precipitated, filtered with suction, and the crude product is washed with ethanol to obtain the pure product 2-(1H-benzo[d]imidazole)-3-(4-methylphenyl)- Acrylonitrile,

[0025]

[0026] Yield: 79%; yellow solid; H NMR spectrum (DMSO-d 6 , 400MHz) (δ, ppm): 13.06(s, 1H), 8.31(s, 1H), 7.90(d, J=8.4Hz, 2H), 7.69(d, J=7.6Hz, 1H), 7.55(d , J=7.6Hz, 1H), 7.42(d, J=8.4Hz, 2H), 7.30-7.21(m, 2H), 2.41(s, 3H).

Embodiment 3

[0028] Step 1) Add 2-cyanomethylbenzimidazole (1.0mmol), benzaldehyde (1.0mmol), carbon tetrabromide (0.1mmol) and absolute ethanol 2mL in a 25mL round bottom flask, and react under reflux for 8 minute;

[0029] Step 2) After the reaction is completed, cool to room temperature, a large amount of product is precipitated, suction filtered, and the crude product is washed with ethanol to obtain pure product 2-(1H-benzo[d]imidazole)-3-phenylacrylonitrile,

[0030]

[0031] Yield: 91%; Pale yellow solid; H NMR spectrum (DMSO-d 6 , 400MHz) (δ, ppm): 13.12 (s, 1H), 8.37 (s, 1H), 8.02-8.00 (m, 2H), 7.70-7.57 (m, 5H), 7.27 (s, 2H).

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Abstract

The invention discloses a preparation method of α-cyanoarylvinylbenzimidazole, which comprises putting aromatic aldehyde, 2-cyanomethylbenzimidazole, carbon tetrabromide and solvent ethanol into a reactor, and After the reaction, cool to room temperature, the product is precipitated, and the crude product is obtained by suction filtration; the crude product is washed with ethanol to obtain the pure product of α-cyanoaryl vinyl benzimidazole. The reaction raw materials of the invention are cheap and easy to obtain, mild reaction conditions, less side reactions, short time consumption, high yield, low cost, energy saving, easy purification, convenient post-treatment, environmental friendliness, and easy industrial production.

Description

technical field [0001] The present invention relates to a preparation method of α-cyanoaryl vinyl benzimidazole. Background technique [0002] α-Cyanoarylvinylbenzimidazoles have excellent anticancer (Journal of Medicinal Chemistry, 2004, 47, 3438) and anti-HIV-1 virus (European Journal of Medicinal Chemistry, 2015, 95, 500) activities. The development of simple and efficient methods for the synthesis of such compounds is of great significance for the development and research of new drugs. [0003] At present, the preparation method of the α-cyanoaryl vinyl benzimidazole of bibliography mainly contains following two kinds: [0004] 1) Aromatic aldehyde and 2-cyanomethyl benzimidazole are used as raw materials, ethanol is used as a solvent, and piperidine is used as a catalyst to react under reflux conditions to obtain α-cyanoaryl vinyl benzimidazole. [0005] [0006] This method requires the use of flammable, highly toxic and volatile organic base piperidine as a react...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/16
CPCC07D235/16
Inventor 王翔陈平胡华友支三军韦长梅
Owner HUAIYIN TEACHERS COLLEGE