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A method for preparing arylsulfonic acid compounds based on c-h activation of arylamines

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: 2019-04-09
ZHEJIANG UNIV OF TECH
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  • 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

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  • A method for preparing arylsulfonic acid compounds based on c-h activation of arylamines
  • A method for preparing arylsulfonic acid compounds based on c-h activation of arylamines
  • A method for preparing arylsulfonic acid compounds based on c-h activation of arylamines

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, and 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...

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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

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Application Information

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Patent Type & Authority Patents(China)
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
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