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Method for synthesizing alpha-aryl-beta-sulfonyl amide

A technology for sulfonyl amide and sulfonyl acrylamide, which is applied in the field of synthesizing α-aryl-β-sulfonyl amide, can solve the problems of high reaction cost, many reaction steps, complicated production process and the like, and achieves convenient post-processing, Effects that are easy to operate and simple to synthesize

Inactive Publication Date: 2015-01-07
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although it is widely used, in the specific synthesis process, the production process is complicated and the reaction steps are many, which makes the cost of the reaction large.

Method used

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  • Method for synthesizing alpha-aryl-beta-sulfonyl amide
  • Method for synthesizing alpha-aryl-beta-sulfonyl amide
  • Method for synthesizing alpha-aryl-beta-sulfonyl amide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The molar ratio of N-phenylsulfonylacrylamide to p-toluenesulfonylhydrazide is 1:1.2, acetonitrile is used as solvent, and the amount of oxidant tert-butyl hydroperoxide is N-phenyl N-sulfonylacrylamide The molar ratio is 2 times.

[0028] Add 4.7g of N-phenylsulfonyl hydrazide acrylamide and 3.4g of p-toluenesulfonyl hydrazide to the round bottom flask, add 1.1g of copper trifluoromethanesulfonate, dissolve with acetonitrile and add the oxidant tert-butyl hydroperoxide 3.9 g, the above solution was reacted at 80°C for 3 hours.

[0029] Concrete reaction formula is as follows:

[0030]

[0031] After the reaction was completed, the product was separated and purified by column chromatography to obtain the corresponding α-phenyl-β-p-toluenesulfonylamide. The corresponding melting point was 177°C and the yield was 87%.

[0032] 1 H NMR (500MHz, CDCl 3 )δ7.52(d, J=8.3Hz, 2H), 7.31(d, J=7.5Hz, 2H), 7.26(t, J=8.1Hz, 3H), 7.17(dd, J=13.4, 8.2Hz, 4H), 7.07(dd, J=15.4, ...

Embodiment 2

[0034] The molar ratio of N-phenylsulfonyl hydrazide acrylamide to p-toluenesulfonyl hydrazide is 1:1.5, add raw materials into the flask and add 4.7g of N-phenylsulfonyl hydrazide acrylamide, p-toluenesulfonyl Hydrazine 4.2g, add copper trifluoromethanesulfonate 1.1g, after dissolving with acetonitrile, add oxidant tert-butyl hydroperoxide 3.9g, other operation is the same as embodiment 1.

[0035] After the reaction was completed, the product was separated and purified by column chromatography to obtain the corresponding α-phenyl-β-p-toluenesulfonylamide. The corresponding melting point was 177° and the yield was 84%.

Embodiment 3

[0037] The molar ratio of N-phenyl N-sulfonyl hydrazide acrylamide to p-toluenesulfonyl hydrazide is 1:2, add raw materials into the flask and add 4.7g of N-phenyl N-sulfonyl hydrazide acrylamide, p-toluene sulfonyl hydrazide Benzenesulfonyl hydrazide 5.6g, add copper trifluoromethanesulfonate 1.1g, add oxidant tert-butyl hydroperoxide 3.9g after dissolving with acetonitrile, other operations are the same as embodiment 1

[0038] After the reaction was completed, the product was separated and purified by column chromatography to obtain the corresponding α-phenyl-β-p-toluenesulfonylamide. The corresponding melting point was 177°, and the yield was 80%.

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Abstract

The invention discloses a method for synthesizing alpha-aryl-beta-sulfonyl amide. The method comprises the following steps: mixing N-phenyl N-sulfonyl acrylamide compounds with p-methyl benzenesulfonyl hydrazide to obtain a mixture; then, adding a catalyst into the mixture, adding an oxidant into the mixture after dissolving the catalyst with a solvent, and reacting for 1-10 hours at 0-150 DEG C; and after the reaction is completed, separating and purifying the mixture to obtain alpha-aryl-beta-sulfonyl amide, wherein a structural formula of the N-phenyl N-sulfonyl acrylamide compounds is as shown in formula (I) described in the specification, a structural formula of the alkyl sulfonyl hydrazine is as shown in formula (II) described in the specification and a structural formula of the alpha-aryl-beta-sulfonyl amide compound is as shown in formula (III) described in the specification, wherein Ar1, Ar2 and Ar3 are independently selected from alkyl or substituted alkyl; a substituent group on substituted alkyl is alkyl with a carbon number of 5-6, alkoxy with a carbon number of 3-6 or halogen.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing α-aryl-β-sulfonylamide. Background technique [0002] Looking at the application of antibacterial drugs in the past ten years, sulfonamide compounds have been widely used in clinical drug research due to their unique antibacterial properties, stable properties, easy use, and low price. At present, with the in-depth research of scientists, it has been found that sulfonamide compounds have a wider range of biological activities, such as anti-tumor, diuretic, anti-thyroid, anti-hypoglycemia, and treatment of cataracts. Although it is widely used, in the specific synthesis process, the production process is complicated and the reaction steps are many, which makes the cost of the reaction high. Contents of the invention [0003] The invention provides a method for synthesizing α-aryl-β-sulfonylamide, which utilizes catalytic oxidation reaction, has simple ...

Claims

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Application Information

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IPC IPC(8): C07C315/04C07C317/44
Inventor 李小青许响生胡培珠
Owner ZHEJIANG UNIV OF TECH
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