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Method for preparing 3,4-diamino-benzenesulfonamide

A technology for diaminobenzenesulfonamide and o-nitroaniline is applied in the field of preparing 3,4-diaminobenzenesulfonamide, and can solve the problems of difficulty in industrialization, complicated operation, slow reaction rate and the like

Inactive Publication Date: 2014-02-05
ZHENGZHOU SIGMA CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The traditional method for synthesizing 3,4-diaminobenzenesulfonamide is complicated in operation, slow in reaction rate, expensive in raw materials, and cumbersome in post-treatment process. From the perspective of safety and cost, it is difficult to realize industrialization

Method used

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  • Method for preparing 3,4-diamino-benzenesulfonamide

Examples

Experimental program
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Effect test

Embodiment 1

[0018] ① Add 100g of chlorosulfonic acid into the reaction bottle, stir and control the temperature at 0°C, slowly add 30g of o-nitroaniline in batches, control the system temperature at 0°C and continue to stir for 2 hours. After the reaction is completed, pour the reaction product into ice water and stir for 0.5 Filtrate after h to obtain 51.4g of solid intermediate a, then slowly add intermediate a in batches to 300g of ammonia water with a concentration of 30% by mass, control the temperature at 5°C and stir for 0.5h, and steam out the reaction solution after the reaction is completed After filtering and drying the precipitated solids, 45.7 g of intermediate b was obtained for use (yield: 96%).

[0019] ② Add 45.7g of intermediate b, 0.5g of ferric chloride, 2.74g of activated carbon, and 274g of ethanol in sequence in a reaction flask with a reflux device, and heat up to 70°C to condense and reflux. At the beginning of reflux, slowly add hydrazine hydrate dropwise, while ...

Embodiment 2

[0021] ①Add 100g of chlorosulfonic acid into the reaction bottle, stir and control the temperature at 5°C, slowly add 25g of o-nitroaniline in batches, control the system temperature at 0°C and continue to stir for 2h. After the reaction is completed, pour the reaction product into ice water and stir for 0.5 Filtrate after h to obtain 42.8g of solid intermediate a, then slowly add intermediate a in batches to 400g of ammonia water with a concentration of 25% by mass, control the temperature at 10°C and stir for 0.5h, and steam out the reaction solution after the reaction is completed The water and the precipitated solid matter were filtered and dried to obtain 38 g of intermediate b for use (yield: 96%).

[0022] ② Add 38g of intermediate b, 0.38g of ferric chloride, 1.9g of activated carbon, and 190g of ethanol in sequence in a reaction flask with a reflux device, and heat up to 60°C to condense and reflux. For reaction, 38g of hydrazine hydrate was added dropwise, and the r...

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Abstract

The invention discloses a method for preparing 3,4-diamino-benzenesulfonamide, and belongs to the field of organic synthesis. The method comprises the following steps: 1, reacting a chlorosulfonic acid with ortho-nitroaniline to prepare an intermediate a, and reacting the intermediate a with ammonia water to prepare an intermediate b for later use; 2, reacting the intermediate b with iron chloride and hydrazine hydrate to prepare a 3,4-diamino-benzenesulfonamide product. The method is safe, simple, easy to operate, low in cost and less in environment pollution, and has high industrial value.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing 3,4-diaminobenzenesulfonamide. technical background [0002] Sulfonamide drugs have the structure of p-aminobenzenesulfonamide, which can be used to prevent and treat bacterial infectious diseases. It has good chemical treatment efficacy in purulent infections such as eye, ear, nose and throat, so that bacterial infectious diseases with high mortality rate have been controlled, creating a new era of chemical treatment. Among them, 3,4-diaminobenzenesulfonamide is a sulfonamide drug intermediate with extremely high pharmaceutical value, which has received more and more attention. [0003] The traditional method for synthesizing 3,4-diaminobenzenesulfonamide is complex in operation, slow in reaction rate, expensive in raw materials, cumbersome in post-treatment process, and difficult to realize industrialization in terms of safety and cost. Ther...

Claims

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Application Information

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IPC IPC(8): C07C311/39C07C303/40
Inventor 杨勇王建莉石田丽徐亚娟段显英
Owner ZHENGZHOU SIGMA CHEM
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