Method for ultrasound-assisted synthesis of N-arylsulfonamide

An aryl sulfonamide, ultrasonic-assisted technology, applied in the preparation of sulfonic acid amide, organic chemistry, etc., can solve the problems of complex reaction conditions, inability to prepare N-aryl fatty sulfonamide, and limit industrial application, and achieve reaction efficiency High, low cost, low price effect

Active Publication Date: 2018-11-16
CENT SOUTH UNIV
View PDF3 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The method has complex reaction conditions, uses toxic and explosive dimethyl sulfoxide as an organic solvent, and cannot prepare N-aryl fatty sulfonamides, which severely limits its industrial application

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 ultrasound-assisted synthesis of N-arylsulfonamide
  • Method for ultrasound-assisted synthesis of N-arylsulfonamide
  • Method for ultrasound-assisted synthesis of N-arylsulfonamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Preparation of N-phenylbenzenesulfonamide (N-phenylbenzenesulfonamide):

[0052]In a 25mL round bottom flask, add 1.23g of nitrobenzene, 2.64g of benzenesulfonyl chloride, 1.96g of iron powder, and 10mL of water in sequence, and react the resulting mixture in a 35W / 40KHz ultrasonic stirring (600 rpm) reaction device for 60 minutes . The reactant was extracted with ethyl acetate and recrystallized to obtain 2.26 g of the corresponding N-phenylbenzenesulfonamide, with a yield of 97%.

Embodiment 2

[0054] Replace 35W / 40KHz ultrasonic stirring with 45W / 40KHz ultrasonic stirring:

[0055] In a 25mL round bottom flask, add 1.23g of nitrobenzene, 2.64g of benzenesulfonyl chloride, 1.96g of iron powder, and 10mL of water in sequence, and react the resulting mixture in a 45W / 40KHz ultrasonic stirring (600 rpm) reaction device for 60 minutes . The reactant was extracted with ethyl acetate and recrystallized to obtain 2.26 g of the corresponding N-phenylbenzenesulfonamide, with a yield of 97%.

Embodiment 3

[0057] Replace 35W / 40KHz ultrasonic stirring with 25W / 40KHz ultrasonic stirring:

[0058] In a 25mL round bottom flask, add 1.23g of nitrobenzene, 2.64g of benzenesulfonyl chloride, 1.96g of iron powder, and 10mL of water in sequence, and react the resulting mixture in a 25W / 40KHz ultrasonic stirring (600 rpm) reaction device for 60 minutes . The reactant was extracted with ethyl acetate and recrystallized to obtain 1.98 g of the corresponding N-phenylbenzenesulfonamide, with a yield of 85%.

[0059] From Examples 1, 2 and 3, it can be known that adjusting the power of ultrasound can affect the yield of the product. Research has found that the yield of the product can be further improved at a power of 35W or above.

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 ultrasound-assisted synthesis of N-arylsulfonamide. N-arylsulfonamide compound is synthesized by series reaction of nitro reduction/sulfonyl chloride reduction/sulfonamidation with taking aromatic nitro compounds, sulfonyl chloride and iron powder as raw materials under ultrasonic stirring conditions. Water is used as a reaction medium and a hydrogen source inthe reaction. The method has the advantages of cheap and easily obtained raw materials, simple and mild reaction conditions, environmental friendliness, saving energy, high reaction selectivity and high yield, excellent compatibility of substrate functional groups and high application value.

Description

technical field [0001] The invention relates to a method for synthesizing N-aryl sulfonamides, in particular to a method for synthesizing N-aryl sulfonamides under ultrasonic stirring conditions, and belongs to the technical field of organic intermediate synthesis. Background technique [0002] Sulfonamide compounds are a very important class of heteroatom compounds, which not only have a wide range of pharmacological activities, but also are important synthetic intermediates in organic synthesis. The nucleophilic reaction between aromatic amine compounds and sulfonyl chlorides is the most important method for the synthesis of N-aryl sulfonamide compounds, but most aromatic amine compounds are prepared by hydrogenation reduction of aromatic nitro compounds, and the functional group tolerance is affected to a certain extent. lead to an increase in product cost. [0003] In 2015, Professor Luo Meiming from Sichuan reported the only case of the direct preparation of N-aryl ary...

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): C07C303/36C07C311/21C07D333/34C07D213/71C07C311/08C07D213/76
CPCC07C303/36C07D213/71C07D213/76C07D333/34C07C311/21C07C311/08
Inventor 肖芳曾明关岚肖元元
Owner CENT SOUTH UNIV
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