Supercharge Your Innovation With Domain-Expert AI Agents!

Method for synthesizing 2-cyano-5-aryl-1H-imidazole compound

A compound and imidazole technology, applied in the field of pesticide technical and intermediate synthesis, can solve the problems of complex treatment process, harsh reaction conditions, and many waste water, etc., and achieve the effects of high yield and simple operation.

Pending Publication Date: 2020-05-05
XIAN MODERN CHEM RES INST
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw material n-butyllithium used in this method is expensive, and the reaction requires a low temperature of -70°C, the reaction conditions are harsh, and there is a lot of wastewater in the butyllithium treatment process, causing water pollution; The method of introducing cyano group at the 2-position of imidazole ring by imine structure
The raw material 1-methoxy-1-imino-2,2-diethoxyethane used in this method is not easy to prepare, perishable, and expensive; , and then using the aldoxime group to introduce the cyano group at the 2-position of the imidazole ring, the synthesis of the intermediate 4(5)-chloro-2-cyano-5(4)-(4'-methylphenyl)imidazole adopts Sulfur monochloride is used as chlorinating agent and reducing agent, and the particle size of the sulfur produced by the reaction is extremely fine, and the treatment process is more complicated. In the reaction, N,N-dimethylformamide is used as the solvent, and the solvent cannot be recovered
The above methods have disadvantages such as expensive raw materials, harsh operating conditions or unrecoverable solvents.

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 synthesizing 2-cyano-5-aryl-1H-imidazole compound
  • Method for synthesizing 2-cyano-5-aryl-1H-imidazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 27.8g of α,α-dibromophenylethanone, 139g of methanol, 34.7g of 60% aqueous solution of 2,2-dimethoxyacetaldehyde, 30.4g of triethylamine, and 29.6g of ammonium acetate were added with a thermometer, refluxing In a three-necked round-bottomed flask of a condenser and a stirring device; heat up to 40°C under stirring, stir the reaction, monitor the reaction by TLC, the raw material α,α-dibromophenylethanone disappears to complete the reaction (about 10h); add water at 40°C 139g was stirred for 1h, a large amount of solid was formed, and the crude product was obtained by filtration; the above-mentioned filtered solid was beaten with 50g of warm water at 40°C, stirred for 1h, filtered, and dried to obtain the product 2-(dimethoxymethyl)-5-phenyl-1H-imidazole 19.2g, yield 91%, content 96.3%.

Embodiment 2

[0026] 18.9g of α,α-dichlorophenylethanone, 139g of methanol, 34.7g of 60% aqueous solution of 2,2-dimethoxyacetaldehyde, 30.4g of triethylamine, and 29.6g of ammonium acetate were added in sequence with a thermometer, refluxing In the three-necked round-bottomed flask of the condenser and stirring device; heat up to 40°C under stirring, stir the reaction, monitor the reaction by TLC, the raw material α,α-dichlorophenylethanone disappears to complete the reaction (about 16h); add water at 40°C 139g was stirred for 1h, a large amount of solid was formed, and the crude product was obtained by filtration; the above-mentioned filtered solid was beaten with 50g of warm water at 40°C, stirred for 1h, filtered, and dried to obtain the product 2-(dimethoxymethyl)-5-phenyl-1H-imidazole 18.4g, yield 84.3%, content 95.8%.

Embodiment 3

[0028] 27.8g of α,α-dibromophenylethanone, 139g of methanol, 34.7g of 60% aqueous solution of 2,2-dimethoxyacetaldehyde, 30.4g of triethylamine, and 19.2g of ammonium carbonate were added in sequence with a thermometer, refluxing In a three-necked round-bottomed flask of a condenser and a stirring device; heat up to 40°C under stirring, stir the reaction, monitor the reaction by TLC, the raw material α,α-dibromophenylethanone disappears to complete the reaction (about 10h); add water at 40°C 139g was stirred for 1h, a large amount of solid was formed, and the crude product was obtained by filtration; the above-mentioned filtered solid was beaten with 50g of warm water at 40°C, stirred for 1h, filtered, and dried to obtain the product 2-(dimethoxymethyl)-5-phenyl-1H-imidazole 19.7g, yield 90.2%, content 96.1%.

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 synthesizing a 2-cyano-5-aryl-1H-imidazole compound. According to the method, [alpha], [alpha]-dihalogen aryl ethanone and 2, 2-dialkoxy acetaldehyde are used as raw materials and subjected to ring closing with a nitrogen source under the action of an acid-binding agent to synthesize a 2-(dialkoxymethyl)-5-aryl-1H-imidazole compound, and then oximation, dehydration and other reactions are performed to prepare the 2-cyano-5-aryl-1H-imidazole compound. The yield of the 2-(dialkoxymethyl)-5-aryl-1H-imidazole prepared by adopting the synthesis method is as highas 91%, the product purity is 98.0% or above, the yield of the 2-cyano-5-aryl-1H-imidazole compound synthesized by four steps is greater than or equal to 82%, and the method disclosed by the invention is simple in process, mild in reaction condition and cheap and easily available in raw materials. The method is mainly applied to synthesis of medical and pesticide intermediates.

Description

technical field [0001] The invention belongs to the field of pesticide technical and intermediate synthesis, in particular to a method for synthesizing 2-cyano-5-aryl-1H-imidazole compounds. Background technique [0002] 2-(Dialkoxymethyl)-5-aryl-1H-imidazole compounds can form a bare aldehyde group by acidifying and removing the acetal protection at the 2-position dialkoxymethyl group. The aldehyde group has high reactivity and can be easily The conversion reaction of the functional group generates derivatives such as carboxyl, primary alcohol, amide, imine, cyano, etc. Similar derivatives can be used as intermediates to synthesize a variety of biologically active molecules, such as 2-cyano-5-p-tolyl- 1H-imidazole is an important intermediate in the synthesis of 4-chloro-2-cyano-N,N-dimethyl-5-p-tolylimidazole-1-sulfonamide, 4-chloro-2-cyano-N,N -Dimethyl-5-p-tolylimidazole-1-sulfonamide is a new type of imidazole fungicide developed by Japan Ishihara Sangyo Co., Ltd. It h...

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): C07D233/90
CPCC07D233/90
Inventor 杨翠凤陈涛徐泽刚苏天铎戎豪杰宁斌科卫天琪毛明珍张媛媛
Owner XIAN MODERN CHEM RES INST
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com