Synthesis method of 4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide

A kind of technology of oximinylmethine imidazole and methyl phenyl, which is applied in 4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole- In the field of synthesis of 1-sulfonamide, it can solve the problems of complex post-treatment process, severe exotherm, and long reaction time.

Active Publication Date: 2014-07-23
XIAN MODERN CHEM RES INST
View PDF5 Cites 16 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the use of sulfur chloride in this method, and the exothermic heat in the reaction is severe, the re

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
  • Synthesis method of 4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] 1) Synthesis of 2-carbonyl-2-p-benzyl acetaldehyde

[0014] Add 36.6g (0.33mol) of selenium dioxide, 150ml of dioxane, and 10ml of distilled water into a 250ml four-neck flask equipped with a thermometer, a stirrer and a reflux condenser, stir and heat up to 50°C, add 40.4g (0.3mol) For p-methylacetophenone, heat up to 110°C for 5 hours, cool to room temperature, remove the filter residue by filtration, concentrate the filtrate to dryness under reduced pressure, add 80ml of petroleum ether for beating, filter to obtain a reddish-brown solid, use petroleum ether:ethyl acetate= 10 (volume ratio) recrystallized to obtain a purity of 98.5% and a yield of 82.3%.

[0015] 2) Synthesis of 4-hydroxy-4(5)-(4-methylphenyl)-2-oximinomethymidazolium-3-oxo

[0016] Add 44.4g (0.3mol) 2-carbonyl-2-p-benzyl acetaldehyde, 104.3g (1.50mol) hydroxylamine hydrochloride, 200ml methanol and 100ml of water, heated to reflux, reacted for 2 hours, then added 47.9g (0.33mol) 40% glyoxal aqueo...

Embodiment 2

[0028] 1) Synthesis of 2-carbonyl-2-p-benzyl acetaldehyde

[0029] Add 50.0g (0.45mol) of selenium dioxide, 150ml of dioxane, and 10ml of distilled water into a 250ml four-neck flask equipped with a thermometer, a stirrer and a reflux condenser, heat up to 50°C under vigorous stirring, and add 40.4g (0.3mol) mol) p-methyl acetophenone, warming up to 110°C for 5 hours reaction, then cooling the reaction solution to room temperature, filtering to remove the selenium generated, concentrating the filtrate to dryness under reduced pressure, adding 80ml of petroleum ether for beating, and filtering to obtain a reddish-brown solid, Recrystallized with petroleum ether: ethyl acetate = 10 (volume ratio), the purity was 98.5%, and the yield was 83.2%.

[0030] 2) Synthesis of 4-hydroxy-4(5)-(4-methylphenyl)-2-oximinomethymidazolium-3-oxo

[0031] Add 44.4g (0.3mol) 2-carbonyl-2-p-benzyl acetaldehyde, 104.3g (1.50mol) hydroxylamine sulfate, 200ml methanol and 100ml of water, heated to ...

Embodiment 3

[0038] The method is basically the same as in Example 2, except that the solvent in step 3) is replaced by dichloroethane and N,N-dimethylformamide. Based on p-methyl acetophenone, the total yield of cyafamid was 45.7%, and the purity was 89.2%.

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 synthesis method of 4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide (cyazofamid). According to the synthesis method, methylacetophenone is taken as a raw material, selenium dioxide is used for oxidation to prepare an intermediate, namely 2-carbonyl-2-p-benzyl aldehyde, then N,N-dimethylformamide and the like are taken as solvents, thionyl chloride is taken as a chlorinating agent and reducing agent for preparing the intermediate, and then intermediate further reacts with N,N-dimethyl sulfonamide chloride to synthesize the cyazofamid. Compared with the prior art, the synthesis method has the advantages that the reaction period is shortened, the post-treatment process is simplified and the synthesis method is suitable for mass industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing 4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide (cyazofamid). Background technique [0002] 4-Chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide (cyanazifazol) was developed by Japan Ishihara Sangyo Co., Ltd., The new generation of imidazole fungicides jointly developed with BASF is mainly used to prevent and control diseases caused by oomycete pathogens, such as: potato late blight, tomato late blight, grape downy mildew, cucumber downy mildew, etc. It has very good protective activity, long residual effect, and is resistant to rain erosion. It can be used for both soil treatment and foliar spray, and has very low toxicity and good environmental compatibility. European Patent EP0705823A1 discloses a preparation method of Cyazofamid, which uses 2,2-dichloro-4'-methylacetophenone as raw material, first cyclizes with hydroxylamine and glyoxal, and then...

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): C07D233/90
CPCC07D233/90
Inventor 陈涛杨翠凤苏天铎宁斌科张建功王列平林双政王月梅
Owner XIAN MODERN CHEM RES INST
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