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Method for preparing phenylamide compound

A technology for phenylamides and compounds is applied in the field of preparing phenylamides, and can solve the problems of polluted environment, high reaction temperature, long reaction time and the like

Inactive Publication Date: 2012-05-02
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The purpose of the present invention is to overcome the deficiencies in the prior art, to provide a method for preparing phenylamides, which overcomes the shortcomings of high copper-catalyzed coupling reaction temperature and long reaction time, and avoids the disadvantages of palladium-catalyzed coupling reaction. Defects of high cost and polluting the environment

Method used

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  • Method for preparing phenylamide compound

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Effect test

Embodiment 1

[0026] Embodiment one: a kind of preparation has N, the method for N-diphenylacetamide comprises the following process steps:

[0027] Add iodobenzene (201mg, 1.00mmol), acetanilide (178mg, 1.21mmol), cuprous iodide (9.5mg, 0.050mmol, 5.0mol%), 1,1'-bis(diphenyl Phosphine) ferrocene (27.7mg, 0.050mmol, 5.0mol%), potassium phosphate (318mg, 1.50mmol), adding 5.0mL N, N-dimethylformamide; the reaction solution was reacted at 110°C for 12h, and the resulting The reddish-brown solution is filtered through a sand core funnel to remove solid impurities, and then separated through a 200-300 mesh silica gel column (the eluent is 1:5 ethyl acetate / petroleum ether), and after removing the solvent, N,N-diphenyl Acetamide, the structural formula is: The yield was 80%. 1H NMR (400MHz, CDCl3): 2.08 (s, 3H), 7.01-7.32 (m, 6H), 7.69 (d, J=7.2Hz, 4H). MS (m / z): 211 (M+).

Embodiment 2

[0028] Embodiment two: a kind of method for preparing N-phenyl-N-(4-methylphenyl) acetamide comprises the following process steps:

[0029] Add p-bromotoluene (171mg, 1.00mmol), acetanilide (270mg, 2mmol), cuprous bromide (14.3mg, 0.100mmol, 10.0mol%), 1,1'-bis(diphenyl Phosphine) ferrocene (110mg, 0.200mmol, 20.0mol%), potassium phosphate (318mg, 1.50mmol), add 5.0mL N,N-dimethylformamide, react the reaction solution at 80°C for 24h, the resulting reddish-brown The solution is filtered through a sand core funnel to remove solid impurities, and then separated by a 200-300 mesh silica gel column (eluent is 1:5 ethyl acetate / petroleum ether), and after removing the solvent, N-phenyl-N-(4 -Methylphenyl) acetamide, structural formula is:

[0030] Yield: 75%. 1H NMR (400 MHz, CDCl3): 2.08 (s, 3H), 2.32 (s, 3H), 7.12-7.40 (m, 9H). MS (m / z): 225 (M+).

Embodiment 3

[0031] Embodiment three: a kind of preparation N, the method for N-bis (4-methylphenyl) acetamide comprises the following processing steps:

[0032] Add p-bromotoluene (171mg, 1.00mmol), p-methylacetanilide (149mg, 1.00mmol), cuprous iodide (3.8mg, 0.020mmol, 2.0mol%), 1,1'-bis (Diphenylphosphine)ferrocene (11.1mg, 0.020mmol, 2.0mol%), potassium phosphate (318mg, 2.00mmol), add 5.0mL dimethyl sulfoxide, and react the reaction solution at 50°C for 24h, resulting in dark red The solution is filtered through a sand core funnel to remove solid impurities, and then separated by a 200-300 mesh silica gel column (eluent is 1:5 ethyl acetate / petroleum ether), and after removing the solvent, N, N-di(4- Methylphenyl) acetamide, structural formula is: The yield was 70%. 1H NMR (400 MHz, CDCl3): 7.48-7.02 (m, 8H), 2.33 (s, 6H), 2.08 (s, 3H). MS (m / z): 239 (M+).

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Abstract

The invention relates to a method for preparing a phenylamide compound, which is characterized by comprising the following steps of: (1) adding aryl halide and amide or an amide derivative into a reaction vessel, adding cuprous halide and 1,1'-bis(diphenylphosphino)ferrocene serving as catalysts, adding alkali and an organic solvent, and reacting at the temperature of between 50 and 150 DEG C for 2 to 24 hours; and (2) filtering reaction liquid obtained in the step (1), purifying by using a silica gel column of 200 to 300 meshes, pre-leaching the silica gel column by using 20 to 50mL of petroleum ether, eluting by using a leacheate at a flow rate of 1 to 2mL / min for 3 to 6 hours, removing the solvent, and thus obtaining the phenylamide compound. By the method, the defects of high temperature and long reaction time of copper-catalyzed coupling reaction and high cost and environmental pollution of palladium-catalyzed coupling reaction are overcome.

Description

technical field [0001] The invention relates to a method for preparing phenylamide compounds, belonging to the technical field of chemical materials. Background technique [0002] Phenylamide compounds have been widely used as pharmaceutical intermediates, fungicides, marine antifouling agents, functional materials, etc., and new uses are constantly being developed. Research on a new method for the preparation of simple phenylamide compounds with low cost and high yield has a large market scenario. [0003] Halogenated benzene coupling amides to prepare the Goldberg reaction of phenylamides is a traditional method, which is the reaction of copper powder (or copper salt)-promoted amides and halogenated benzenes. The disadvantage is that the reaction temperature is high (180 ~ 250°C), long reaction time (tens of hours), part of the reaction requires one mole or more of copper to participate in the reaction, many side reactions, medium yield and cumbersome separation and purif...

Claims

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Application Information

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IPC IPC(8): C07C231/08C07C233/07C07C233/15
Inventor 丁玉强刘新芳张松林朱焯炜王婷
Owner JIANGNAN UNIV
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