Preparation method of bromo-substituted benzimidazole derivative

A technology of benzimidazole and derivatives, applied in the field of novel preparation of pharmaceutical intermediates, can solve problems such as difficulty in synthesis

Inactive Publication Date: 2015-02-25
湖南华腾制药有限公司
View PDF2 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of 5-bromo-1,6-dimethyl-1H-benzo[d]imidazole-2-carbaldehyde is difficult at present

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of bromo-substituted benzimidazole derivative
  • Preparation method of bromo-substituted benzimidazole derivative
  • Preparation method of bromo-substituted benzimidazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] (1) Synthesis of 4-bromo-5-methyl-1,2-phenylenediamine

[0023] Add 36g of 5-bromo-4-methyl-2-nitroaniline to 400ml of ethanol, add 3g of 10% palladium carbon, feed hydrogen, stir overnight, filter, collect the filtrate, concentrate to obtain 27g of 4-bromo-5 -Methyl-1,2-phenylenediamine.

[0024] (2) Synthesis of 5-bromo-2-(diethoxymethyl)-6-methyl-1H-benzo[d]imidazole

[0025] Add 28g of 4-bromo-5-methyl-1,2-phenylenediamine to 350ml of absolute ethanol, add 17g of sodium ethoxide, then add 32g of ethyl 2,2-diethoxyacetate, heat and reflux for 24 hours , cooled, concentrated, added water and ethyl acetate for extraction and separation, collected the organic phase, dried, and concentrated to obtain 19g of 5-bromo-2-(diethoxymethyl)-6-methyl-1H-benzo[ d] imidazole.

[0026] (3) Synthesis of 5-bromo-2-(diethoxymethyl)-1,6-dimethyl-1H-benzo[d]imidazole

[0027] 19g of 5-bromo-2-(diethoxymethyl)-6-methyl-1H-benzo[d]imidazole was added to 150ml of N,N-dimethylformamide,...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a preparation method of a bromo-substituted benzimidazole derivative 5-bromo-1,6-dimethyl-1H-benzo[d]imidazolyl-2-formaldehyde, which comprises the following steps: by using 5-bromo-4-methyl-2-nitroaniline as the initial raw material, carrying out reduction, cyclization, methylation and hydrolysis reaction to obtain the target product. The compound is an important drug intermediate.

Description

technical field [0001] The present invention relates to a novel preparation method of a pharmaceutical intermediate, in particular to the preparation of a bromine-substituted benzimidazole derivative 5-bromo-1,6-dimethyl-1H-benzo[d]imidazole-2-carbaldehyde method. technical background [0002] The compound 5-bromo-1,6-dimethyl-1H-benzo[d]imidazole-2-carbaldehyde has the structural formula: [0003] [0004] The compound 5-bromo-1,6-dimethyl-1H-benzo[d]imidazole-2-carbaldehyde and related derivatives are widely used in medicinal chemistry and organic synthesis. Currently, the synthesis of 5-bromo-1,6-dimethyl-1H-benzo[d]imidazole-2-carbaldehyde is difficult. Therefore, it is necessary to develop a synthetic method with easy-to-obtain raw materials, convenient operation, easy-to-control reaction and suitable overall yield. Contents of the invention [0005] The invention discloses a preparation method of bromine-substituted benzimidazole derivative 5-bromo-1,6-dimethyl...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/12
CPCC07D235/12
Inventor 陈芳军李书耘
Owner 湖南华腾制药有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap