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Method for preparing sulfonamide and derivatives thereof

A technology of derivatives and sulfonamides, which is applied in the field of preparation of sulfonamides and their derivatives, can solve the problems of poor tolerance of functional groups, harsh reaction conditions, and contamination of transition metals, and achieve mild reaction conditions, simple operation, and easy purchase Effect

Inactive Publication Date: 2015-04-08
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these experiments have made great progress in the synthesis of sulfonamide compounds, there are still many shortcomings, such as the danger of raw materials (mutagenic sulfonyl chloride and pretreatment organic azide), harsh reaction conditions, and long reaction time , poor functional group tolerance and the use of transition metals that may lead to contamination, etc.

Method used

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  • Method for preparing sulfonamide and derivatives thereof
  • Method for preparing sulfonamide and derivatives thereof
  • Method for preparing sulfonamide and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) Add sodium benzenesulfinate (1mmol) and I in a round bottom flask 2 (0.5mmol), the mixed solution was stirred at room temperature for 20 minutes, then acetonitrile (2ml) and aniline (0.5mmol) were added, and the mixed solution was stirred at room temperature for 18h.

[0026] (2) After the reaction was completed, 10% concentration of sodium thiosulfate (20ml) was added. Ethyl acetate (20 mL*3) was added to the reaction solution to extract the aqueous phase, and the organic phase was dried over anhydrous sodium sulfate.

[0027] (3) The organic phase was spin-dried by a rotary evaporator, and the product was purified by a silica gel column. The isolated yield of the product N-phenylbenzenesulfonamide was 60%.

Embodiment 2

[0029] (1) Add sodium benzenesulfinate (1mmol) and I in a round bottom flask 2 (0.5mmol), the mixed solution was stirred at room temperature for 20 minutes, then dichloromethane (2ml) and aniline (0.5mmol) were added, and the mixed solution was stirred at room temperature for 18h.

[0030] Steps (2) and (3) are the same as in Example 1, and the isolated yield of the product N-phenylbenzenesulfonamide is 69%.

Embodiment 3

[0032] (1) Add sodium benzenesulfinate (1mmol) and I in a round bottom flask 2 (0.5mmol), the mixed solution was stirred at room temperature for 20 minutes, then water (2ml) and aniline (0.5mmol) were added, and the mixed solution was stirred at room temperature for 18h.

[0033] Steps (2) and (3) are the same as in Example 1, and the isolated yield of the product N-phenylbenzenesulfonamide is 73%.

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Abstract

The invention discloses a method for preparing sulfonamide and derivatives thereof. The method comprises the following step of in the absence of a metal catalyst and in the presence of iodine serving as a catalyst and an oxidant, reacting sodium sulfinate and derivatives of sodium sulfinate with amine and derivatives of amine or ammonia water to form corresponding sulfonamide and derivatives of sulfonamide. According to the method, by adopting the characteristics of mild reaction conditions and no addition of transition metals, alkali, ligand and additives, sulfonamide and derivatives thereof are efficiently prepared, and the method has the advantages of broad substrate range and universality, inexpensive raw materials and mild conditions, easiness for treatment and safety, so that the reaction has good practicability and wide application.

Description

technical field [0001] The invention relates to chemical synthesis, in particular to a preparation method of sulfonamide and derivatives thereof. Background technique [0002] Since sulfonamide compounds are a common structural unit in biologically active ingredients and drug active molecules, they are well known in the fields of anticonvulsants, antibacterial agents, anticancer agents, antitumor agents, anti-inflammatory agents, and inhibition of HIV protease activity. Has a wide range of applications. In addition, due to its easy removal, sulfonamide compounds are also a good amino protecting group. Therefore, many research directions are devoted to the synthesis of sulfonamide compounds. The traditional synthesis method of sulfonamide compounds is derived from sulfonyl chloride and amino compound, and then reacts the primary sulfonamide with aryl halide or aryl boronic acid under transition metal catalyzed conditions. [0003] Recently, the copper-catalyzed reaction of...

Claims

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Application Information

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IPC IPC(8): C07B45/04C07C303/36C07C311/21C07D213/76C07C311/16C07D295/26C07C311/18C07D235/22C07C311/19C07D215/36C07C311/29C07C311/14C07C311/03
Inventor 宋秋玲杨凯
Owner HUAQIAO UNIVERSITY
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