Preparation method of sulfonamide

A technology of sulfonamide and sulfinic acid, which is applied in the preparation of sulfonate amide, organic chemistry, etc., can solve the problems of high activity, sensitivity, and difficulty in storage of sulfonated reagents, and achieve easy industrial production, improved reaction system, and stable properties Effect

Active Publication Date: 2012-09-19
JIANGSU REPONT PESTICIDE FACTORY
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

But also there are some deficiencies in some systems: (1) need to add monophosphine or diphosphine ligand in the reaction to improve yield; (2) need to add a large amount of hygroscopic cesium

Method used

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  • Preparation method of sulfonamide
  • Preparation method of sulfonamide
  • Preparation method of sulfonamide

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Embodiment Construction

[0020] The present invention uses sulfinic acid or sulfinate and nitro compounds in the presence of catalysts and without any additives under an inert gas atmosphere, using transition metals or transition metal compounds as catalysts, and the reaction temperature is 20°C- Heating at 200°C for 3 to 30 hours produces sulfonamides without substantially producing transitional acylation by-products.

[0021]

[0022] The reaction formula of sulfinic acid salt of the present invention and nitro compound

[0023] The technical scheme of the present invention is realized in the following manner: the preferred catalyst is selected from Pd, Ni, Fe, Au, Rh, Pt, Ru, Ir, Ag, Cu, Mn, Co. The metals can optionally be used in elemental form, as complexes or as salts. Particular preference is given to using palladium compounds, also particular preference to copper compounds, more particularly preferably cuprous chloride or cuprous bromide.

[0024] The reaction may optionally be carried o...

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Abstract

The invention discloses a preparation method of sulfonamide, which comprises the step of: under an atmosphere of inert gas, heating sulfinic acid or sulfinate and a nitro compound for 3 to 30 hours at the reaction temperature from 20 DEG C to 200 DEG C by using transition metal or translation metal compound as a catalyst, so as to generate sulfonamide. The preparation method disclosed by the invention has the following technical effects of an improved reaction system and stable properties, low cost and high availability of nitro compound; in this method, the nitro compound is directly used as starting material, thus avoiding the step of selectively reducing nitro into an amino compound; sulfinate is more stable and easier to store than other sulfonating agents; and simultaneously, the reaction system is simple and easy for industrial production. The method disclosed by the invention is safer and more economical and effective than the existing methods, and is also safer in used catalyst; and normally, the method disclosed by the invention can realize the conversion of nitrobenzene raw material into sulfonamide at a conversation rate of 90%, typically above 95%.

Description

technical field [0001] The present invention relates to a method for preparing sulfonamides. Background technique [0002] N-(Substituted phenyl)sulfonamide compounds are important constituents of functional materials, drugs, etc. [ . There are many methods for synthesizing these compounds, which can be roughly classified into two categories: one is the reaction of halogenated aromatic hydrocarbons (or pseudohalogenated aromatic hydrocarbons) and sulfonamides. [ ; One is the reaction of aniline and sulfonated reagent [ . For example, the sulfonamides reported as herbicides in the patent US4,818,275 are by reacting the corresponding arylamine with methanesulfonyl chloride and excess triethylamine in dichloromethane, and then treating the resulting sulfonic acid with sodium hydroxide Amide derivatives. However, when the reaction is carried out on a large scale, the excess triethylamine must be recovered, recycled or disposed of as part of the process, and such recovery / re...

Claims

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Application Information

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IPC IPC(8): C07C311/21C07C311/29C07C311/08C07C303/36
Inventor 邓国军罗佳英周先伢肖福红
Owner JIANGSU REPONT PESTICIDE FACTORY
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