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2,2,2-trifluoro-n-(2-arylsulf)-a rylamide derivatives and preparing method

A technology of aryl acetamide and derivatives, applied in 2 fields, can solve the problems of metal palladium catalyst air instability, high ligand toxicity, high price, etc., and achieve the effects of easy post-processing, small environmental impact, and mild conditions

Inactive Publication Date: 2007-11-14
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0021] The 5th and 6th methods all obtain products in the transition metal catalyzed next step reaction, the conditions are relatively mild, and the yield is very high, but the ligand used is highly toxic, the metal palladium catalyst is unstable to air, and the price is very expensive. These shortcomings are certain. To a certain extent, the use of these two methods in a wider range is limited

Method used

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  • 2,2,2-trifluoro-n-(2-arylsulf)-a rylamide derivatives and preparing method
  • 2,2,2-trifluoro-n-(2-arylsulf)-a rylamide derivatives and preparing method
  • 2,2,2-trifluoro-n-(2-arylsulf)-a rylamide derivatives and preparing method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: 2,2,2-trifluoro-N-(2-p-methylphenylthiophenyl)acetamide. Add 2ml 1,2-dimethoxyethane, 0.5mmol 2,2,2-trifluoro-N-(2-iodophenyl)acetamide, 1.1 equivalent p-methylthiophenol to the sealed tube , 2.0 equivalents of potassium carbonate, 0.05mmol cuprous iodide, 0.1mmol L-proline, under nitrogen protection, stirred at 60°C for 40h. Add 10 ml of water and 20 ml of ethyl acetate to the reaction system cooled to room temperature, stir, filter the insoluble matter, and extract the water layer with 10 ml of ethyl acetate each time until thin layer chromatography shows that there is no product in the water layer. The organic layers were combined, and most of the organic solvent was removed by distillation under reduced pressure, and the residue was separated by silica gel column chromatography (petroleum ether: ethyl acetate=40:1) to obtain the product 2,2,2-trifluoro-N-(2 - p-methylphenylthiophenyl)acetamide.

[0034] The structure is:

[0035]

[0036] Molecular ...

Embodiment 2

[0045]Example 2: 2,2,2-trifluoro N-(4-nitro-2-p-tolylthiophenyl)acetamide, add 3ml of 1,2-dimethoxyethane into the sealed tube, 1.0mmol 2,2,2-trifluoro N-(4-nitro-2-iodophenyl)acetamide, 2.0 equivalents of p-methylthiophenol, 2.5 equivalents of potassium carbonate, 0.10mmol cuprous iodide, 0.20 mmol L-proline, under nitrogen protection, stirred at 60°C for 40h. Add 5 ml of water and 10 ml of ethyl acetate to the reaction system cooled to room temperature, stir, filter the insoluble matter, and extract the water layer with 15 ml of ethyl acetate each time until thin layer chromatography shows no product in the water layer. The organic layers were combined, and most of the organic solvent was removed by distillation under reduced pressure, and the residue was separated by silica gel column chromatography (petroleum ether: ethyl acetate=40:1) to obtain the product 2,2,2-trifluoro-N-(4 -nitro-2-p-tolylthiophenyl)acetamide.

[0046] The structure is:

[0047]

[0048] Molecul...

Embodiment 3

[0057] Example 3: 2,2,2-trifluoro-N-(2-phenylthiophenyl)acetamide, add 2.5ml 1,2-dimethoxyethane into the sealed tube, 0.5mmol 2 , 2,2-trifluoro-N-(2-iodophenyl)acetamide, 1.5 equivalents of thiophenol, 2.5 equivalents of potassium carbonate, 0.05 mmol cuprous iodide, 0.1 mmol L-proline, under nitrogen protection, Stir at 60°C for 40h. Add 10 ml of water and 20 ml of ethyl acetate to the reaction system cooled to room temperature, stir, filter the insoluble matter, and extract the water layer with 10 ml of ethyl acetate each time until thin layer chromatography shows that there is no product in the water layer. The organic layers were combined, and most of the organic solvent was removed by distillation under reduced pressure, and the residue was separated by silica gel column chromatography (petroleum ether: ethyl acetate=80:1) to obtain the product 2,2,2-trifluoro-N-(2 -phenylthiophenyl)acetamide.

[0058] The structure is:

[0059]

[0060] Molecular formula: C 14 h ...

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Abstract

The present invention involves a 2,2,2-trifluoromethyl-N-(2-aryl-thio) aryl-acetamide and preparation methods. Figure structure of the compounds, which, R1, R2, R3 for methyl, methoxy, trifluoromethyl, methoxycarbonyl, and amino. Preparation of the compound: 2,2,2 -trifluoromethyl-N-(2-iodine-aryl) acetamide, aryl thiophenol, potassium carbonate, cuprous iodide and L-proline by 1.0:1.1 -2.0:2.0:0.1:0.2 molar ratio dissolved in 1,2 - dimethoxyethane, at the 55 deg.C to 65 deg.C temperature takes closure reaction for 40 to 45 h; cooling the reaction system to room temperature, adding water and ethyl acetate to dissolve undissolved, after filtration, exteacting water layer with ethyl acetate; organic layer through vacuum distillation to remove most organic solvents, and residual substances is separated by silica gel column chromatography, get product 2,2,2-trifluoromethyl-N-(2- aryl-thio) aryl acetamide. This invention is simple, mild conditions, high yield.

Description

technical field [0001] The invention relates to a 2,2,2-trifluoro-N-(2-arylthio)aryl acetamide derivative and a preparation method thereof. Background technique [0002] As a structural unit, 2-arylthioarylamines widely exist in many natural products, synthetic drugs and luminescent materials with important physiological and pharmacological activities, and some 2-arylthioarylamines themselves have potential Antibacterial and anti-inflammatory effect. For example, excessive biosynthesis of inflammatory mediator prostaglandins in patients with arthritis can lead to redness, swelling and pain at the site of inflammation. Compound 1 containing 2-arylthioarylamine structure can effectively block the metabolism of arachidonic acid into prostaglandins process, thereby relieving the patient’s pain and improving the symptoms of joint redness and swelling; another example is that compound 2 is a newly developed drug for the treatment of Chagas disease (a parasitic disease with a high...

Claims

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Application Information

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IPC IPC(8): C07C323/41C07C319/14
Inventor 张慧曹卫国陈杰
Owner SHANGHAI UNIV
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