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

Method for preparing aryl sulfonic acid compound based on C-H activated arylamine

An arylsulfonic acid and compound technology, which is applied in the field of copper-catalyzed arylamines to prepare arylsulfonic acid compounds, can solve the problems of long reaction time, increased research cost and difficulty, harsh reaction conditions and potential safety hazards, and achieves simple operation process. Effect

Active Publication Date: 2017-06-09
ZHEJIANG UNIV OF TECH
View PDF1 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The traditional sulfonation reaction requires the use of oleum or concentrated sulfuric acid, and the reaction time is long and heating is required. The reaction conditions are harsh and there are safety hazards
The existence of these difficulties has greatly reduced the progress of the research on sulfonation reaction, and increased its research cost and difficulty

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 aryl sulfonic acid compound based on C-H activated arylamine
  • Method for preparing aryl sulfonic acid compound based on C-H activated arylamine
  • Method for preparing aryl sulfonic acid compound based on C-H activated arylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 2-(Benzenesulfonic acid)aniline

[0023]

[0024] Add 0.5mmol of aniline (1a) into 4mL of water, add 0.125mmol of copper acetate, 1.0mmol of sodium benzenesulfinate, and 1.0mmol of hydrogen peroxide, and react at room temperature for 2 hours. After the reaction, add saturated NaCl to the reaction solution The aqueous solution was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness at 60°C under reduced pressure to obtain the crude compound represented by the formula (2a). The crude compound represented by the formula (2a) was subjected to silica gel column chromatography, and a solution with a volume ratio of ethyl acetate and petroleum ether of 1:2 was used as the mobile phase, and the eluent with an Rf value of 0.3-0.5 was tracked and collected by TLC. The obtained eluent was desolventized under reduced pressure and dried to obtain 55 mg of the pure compound represented by formula (2a),...

Embodiment 2

[0027] 2-Methyl-6-(benzenesulfonic acid)aniline

[0028]

[0029] Add 0.5mmol of o-toluidine (1b) into 4mL of water, add 0.125mmol of copper acetate, 1.0mmol of sodium benzene sulfinate, and 1.0mmol of hydrogen peroxide, and react at room temperature for 2 hours. After the reaction, add Saturated NaCl aqueous solution was extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness at 60°C under reduced pressure to obtain the crude compound represented by the formula 2b. The crude compound shown in formula 2b was subjected to silica gel column chromatography, with a solution of ethyl acetate and petroleum ether at a volume ratio of 1:2 as the mobile phase, and the eluent with an Rf value of 0.3-0.5 was tracked and collected by TLC, and the obtained The solvent was removed from the eluent under reduced pressure and dried to obtain 51 mg of the pure compound represented by formula 2b, with a yield of 41%.

[...

Embodiment 3

[0032] 4-Methyl-2-(benzenesulfonic acid)aniline

[0033]

[0034] Add 0.5mmol p-toluidine (1c) to 4mL of water, add 0.125mmol copper acetate, 1.0mmol sodium benzene sulfinate, 1.0mmol hydrogen peroxide, and react at room temperature for 2 hours. After the reaction, add Saturated NaCl aqueous solution was extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness at 60°C under reduced pressure to obtain the crude compound represented by the formula (2c). The crude compound represented by formula (2c) was subjected to silica gel column chromatography, using a solution with a volume ratio of ethyl acetate and petroleum ether of 1:2 as the mobile phase, followed by TLC to collect the eluent with an Rf value of 0.3-0.5, and collected The obtained eluent was desolventized under reduced pressure and dried to obtain 49 mg of the pure compound represented by formula (2c), with a yield of 40%.

[0035] 1 H NMR (50...

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 belongs to the technical field of organic chemistry and particularly relates to a method for preparing an arylamine sulfonic acid compound from C-H activated arylamine. The method comprises the following steps: with anhydrous copper acetate as a reaction catalyst and hydrogen peroxide as an oxidizing agent, adding an aniline compound and sodium benzene sulfinate into water; reacting at room temperature for two hours; extracting with ethyl acetate; performing vacuum concentration to obtain a corresponding crude product of arylamine sulfonic acid compound; and performing column chromatographic isolation and purification to obtain a corresponding pure product. The method provided by the invention has the characteristics of easy operation, mild reaction conditions, short reaction time and environmental friendliness.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a method for preparing arylsulfonic acid compounds from arylamines catalyzed by copper. Background technique [0002] Aminobenzenesulfonic acid substances are mainly used in the preparation of dyes (azo dyes), spices, etc., and are also used as pesticides for the prevention and treatment of wheat rust. They are also used in chromatographic analysis reagents in organic synthesis, and are an important chemical synthesis intermediate. body. [0003] The traditional sulfonation reaction requires the use of oleum or concentrated sulfuric acid, and the reaction time is long and heating is required. The reaction conditions are harsh and there are safety hazards. The existence of these difficulties has greatly reduced the progress of the research on sulfonation reaction, and increased its research cost and difficulty. Therefore, it is necessary to find a simple an...

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): C07C315/02C07C317/36
CPCC07C315/02C07C317/36
Inventor 朱勍方红梨朱伸孙宗国
Owner ZHEJIANG UNIV OF TECH
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