Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing 2-aminobenzimidazole derivative

A technology for aminobenzimidazole and derivatives, which is applied in the field of preparation of 2-aminobenzimidazole derivatives, can solve the problems of long route, hindering the practical application of the reaction, and difficulty in obtaining reaction raw materials, etc., and achieves the effect of high synthesis yield

Inactive Publication Date: 2011-05-18
TSINGHUA UNIV
View PDF0 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The preparation method of 2-aminobenzimidazole has at present: 1) S N Ar reaction, this reaction mainly utilizes 2-chlorobenzimidazole and amine to generate nucleophilic substitution reaction, usually requires high temperature and high pressure, although the metal palladium catalysis developed later has improved this reaction, but this reaction raw material is difficult to obtain, greatly hinders the practical application of the reaction
2) The polymerization method of o-phenylenediamine and cyanamide, the mixture of o-phenylenediamine and cyanamide is irradiated with microwaves, and NaOH is used as a catalyst. This method is green and environmentally friendly but can only prepare one type of aminoimidazole
Three) the o-fluoronitrobenzene method utilizes the strong electron-withdrawing effect of nitro, first introduces a compound of o-phenylenediamines, and then synthesizes 2-aminobenzimidazoles compounds through a series of reductive cyclization reactions. Methods tend to have longer routes and lower final yields

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
  • Method for preparing 2-aminobenzimidazole derivative
  • Method for preparing 2-aminobenzimidazole derivative
  • Method for preparing 2-aminobenzimidazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1, N, the preparation of 1-dicyclohexyl-2-aminobenzimidazole

[0024] To a 20mL reactor, add 2-bromoaniline (0.5mmol, 86mg), cuprous iodide (0.05mmol, 10mg), sodium tert-butoxide (1.0mmol, 96mg), N,N-dicyclohexyl carbon Dicyclohexylcarbodiimide (DCC) (0.5 mmol, 103 mg), and finally 1 mL of NMP was added as a solvent, the reactor was sealed, and reacted at 110° C. for 24 h. After the reaction system was cooled, 2 mL of water and 5 mL of ethyl acetate were added and stirred for 30 min, then extracted three times with 15 mL of ethyl acetate, and the organic phases were combined. The organic phase was washed with saturated brine, and finally dried with anhydrous magnesium sulfate for 2 h. After filtration, the organic phase was rotary evaporated to obtain a crude product. The crude product was separated by column chromatography with petroleum ether: ethyl acetate=3:1 (v / v) as the eluent and silica gel as the adsorption phase to obtain a light brown solid product...

Embodiment 2

[0027] Embodiment 2, N, the preparation of 1-dicyclohexyl-6-methyl-2-aminobenzimidazole

[0028]Into a 20mL reactor, add 4-methyl-o-bromoaniline (0.50mmol, 62μL), CuI (0.05mmol, 10mg), sodium tert-butoxide (1.0mmol, 96mg), N,N-dicyclohexyl carbon Dicyclohexylcarbodiimide (DCC) (0.50 mmol, 103 mg), and finally 1 mL of NMP was added as a solvent, the reactor was sealed, and reacted at 110° C. for 24 h. After the reaction system was cooled, 2 mL of water and 5 mL of ethyl acetate were added and stirred for 30 min, then extracted three times with 15 mL of ethyl acetate, and the organic phases were combined. The organic phase was washed with saturated brine, and finally dried with anhydrous magnesium sulfate for 2 h. After filtration, the organic phase was rotary evaporated to obtain a crude product. The crude product was separated by column chromatography with petroleum ether: ethyl acetate=3:1 (v / v) as the eluent and silica gel as the adsorption phase to obtain a light brown sol...

Embodiment 3

[0031] Embodiment 3, N, the preparation of 1-dicyclohexyl-6-fluoro-2-aminobenzimidazole

[0032] To a 20mL reactor, add 4-fluoro-o-bromoaniline (0.50mmol, 57μL), CuI (0.05mmol, 10mg), sodium tert-butoxide (1.0mmol, 96mg), N,N-dicyclohexylcarbodi Dicyclohexylcarbodiimide (DCC) (0.50 mmol, 103 mg), and finally 1 mL of NMP was added as a solvent, the reactor was sealed, and reacted at 110° C. for 16 h. After the reaction system was cooled, 2 mL of water and 5 mL of ethyl acetate were added and stirred for 30 min, then extracted three times with 15 mL of ethyl acetate, and the organic phases were combined. The organic phase was washed with saturated brine, and finally dried with anhydrous magnesium sulfate for 2 h. After filtration, the organic phase was rotary evaporated to obtain a crude product. The crude product was separated by column chromatography with petroleum ether: ethyl acetate=3:1 (v / v) as the eluent and silica gel as the adsorption phase to obtain a light brown soli...

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 method for preparing a 2-aminobenzimidazole derivative. The method comprises the following steps that: in the presence of a copper catalyst and an alkaline compound, 2-halogen phenylamine and carbodiimide are reacted to form the 2-aminobenzimidazole derivative. In the method, the copper catalyst is any of CuI, CuBr and CuCI; and the alkaline compound is tBuONa. The method for preparing the 2-aminobenzimidazole derivative, which is provided by the invention, is scientific and reasonable, the 2-aminobenzimidazole derivative with various substituent groups, which cannot be synthesized by the other method, can be synthesized and obtained, and the method also has the characteristics that synthesis yield is high and a product is easy to purify.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to a method for preparing 2-aminobenzimidazole derivatives. Background technique [0002] 2-aminobenzimidazole (2-aminobenzimidazole, referred to as 2-AB), also known as N, N'-o-phenylene guanidine. White crystal, melting point 231-232℃, is a kind of fine chemical raw material with wide application value. In terms of pesticides, it has strong bactericidal and antibacterial effects on bacteria, fungi, viruses, microorganisms, mites, etc., and can promote the metabolism of cotyledons and roots on asexual plants. In addition, it can also be used as a seed disinfectant. In terms of medicine, because the imidazole ring and benzimidazole heterocycle contained in benzimidazole have anti-parasitic, anti-bacterial, anti-inflammatory, anti-cancer, sedative, diuretic and other drug activities, it is of great significance to coordinate physiological balance. In addition, it also lowers blood pre...

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
IPC IPC(8): C07D235/30
Inventor 席婵娟王飞
Owner TSINGHUA UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com