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Sulfamide benzylation method

A technology of sulfonamide benzyl and sulfonamide, applied in the field of organic chemical synthesis, can solve the problems of unfavorable industrial production, high reaction temperature, high production cost, etc., and achieve the effects of convenient industrial production, high yield and good product quality

Inactive Publication Date: 2014-02-05
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] (1) The reaction temperature is as high as 200°C, with high energy consumption and high production cost
[0005] (2) The method takes a long time to react, which is unfavorable for suitability for industrialized production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] A kind of method of sulfonamide benzylation, its concrete steps are as follows:

[0025] (1) Taking benzyl alcohol and p-toluenesulfonamide as raw materials, boron trifluoride ether as a reagent, and chloroform as a solvent, according to the millimoles of benzyl alcohol: millimoles of p-toluenesulfonamide: BF 3 ·OEt 2 The ratio of millimole: chloroform milliliter is 1: 1.8: 1.2: 2, add benzyl alcohol (108.1mg, 1.0mmol), p-toluenesulfonamide (308.2mg, 1.8mmol) and trichloromethane successively in the reactor Methane (2.0mL), under stirring, added BF 3 ·OEt 2 (151 μL, 1.2 mmol), after the addition was complete, the stirring reaction was continued at 80° C. for 2 hours.

[0026] (2) After step (1) is completed, the reaction solution of benzylsulfonamide prepared in step (1) is concentrated by rotary evaporation, and the concentrated solution is collected; the concentrated solution is purified by silica gel column chromatography, and the eluent After elution, the efflue...

Embodiment 2

[0029] A kind of method of sulfonamide benzylation, its concrete steps are with embodiment 1, wherein:

[0030] In step (1), take benzyl alcohol and benzenesulfonamide as raw materials, boron trifluoride ether is reaction reagent, and chloroform is made solvent, according to benzyl alcohol mmol: benzenesulfonamide mmol: BF 3 ·OEt 2 Millimoles: The ratio of chloroform milliliters is 1:1.8:1.2:2 ratio, successively add benzyl alcohol (108.1mg, 1.0mmol), benzenesulfonamide (282.9mg, 1.8mmol) and chloroform in the reactor (2.0mL), under stirring, add BF 3 ·OEt 2 (151 μL, 1.2 mmol), after the addition was complete, the stirring reaction was continued at 80° C. for 2 hours.

[0031] In step (2), the eluent was a mixture of ethyl acetate:petroleum ether with a volume ratio of 1:(2-40), and N-benzylbenzenesulfonamide (171 mg, yield 69%) was obtained as a white solid.

Embodiment 3

[0033] A kind of method of sulfonamide benzylation, its concrete steps are with embodiment 1, wherein:

[0034] In step (1), benzyl alcohol and methanesulfonamide are used as raw materials, boron trifluoride ether is a reagent, and chloroform is used as a solvent. 3 ·OEt 2 The ratio of millimoles: chloroform milliliters is 1: 1.8: 1.2: 2, successively add benzyl alcohol (108.1mg, 1.0mmol), methanesulfonamide (171.2mg, 1.8mmol) and chloroform in the reactor (2.0mL), under stirring, add BF 3 ·OEt 2 (151 μL, 1.2 mmol), after the addition was complete, the stirring reaction was continued at 80° C. for 2 hours.

[0035] In step (2), the eluent was a mixture of ethyl acetate:petroleum ether with a volume ratio of 1:(2-40), and N-benzylmethanesulfonamide (144 mg, yield 78%) was obtained as a white solid.

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Abstract

The invention relates to a sulfamide benzylation method. According to the sulfamide benzylation method, a finished product is obtained through reaction, concentration and purification by taking various benzyl alcohols and sulfamide as raw materials, boron trifluoride diethyl etherate as a reaction reagent and trichloromethane as a solvent. The sulfamide benzylation method disclosed by the invention has the characteristics of simple method, easiness and convenience for operation, no metal participating reaction, high yield, convenience for application and popularization, and the like, greatly reduces the synthesis cost by taking low-cost benzyl alcohol as a benzylation reagent, can be used for preparing benzyl sulfonamide products with high output rate and multiple varieties and can be widely applied to the industrialized production of benzyl sulfonamides; the product prepared through the sulfamide benzylation method disclosed by the invention can be widely applied to the fields of medicines, pesticides, dyes, engineering plasticizing agents, sterilizing agents, chemical raw materials, and the like and meets the requirements for wide range and large number of the market.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a method for benzylation of sulfonamide. Background technique [0002] Sulfonamide is an important pharmaceutical and pesticide pharmacophore, and its derivatives are often biologically active compounds. In recent years, sulfonamide derivatives have been widely used in production and life, such as: weed control, sterilization, insecticide, anti-cancer, anti-diabetes, etc. In addition, sulfonamide derivatives are also used as plasticizers and dyes for engineering materials. [0003] Existing methods for benzylation of sulfonamides, such as the 2012 publication number CN102617259A "A Method for Dehydration of Alcohol and Amine to Synthesize Amine Compounds" patent, the method disclosed in this patent is to use sulfonamide and alcohol as raw materials, The aldehyde corresponding to the reactant alcohol and the alkali metal salt are used as catalysts,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/36C07C311/16C07C311/03
Inventor 熊燕马航凌学戈何超黄若峰张晓慧潘静李加强
Owner CHONGQING UNIV
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