Process for synthesizing aryl substituted N-aryl amide compounds

A compound and arylamide technology, which is applied in the field of preparation of N-aryl substituted arylamide compounds, can solve the problems of difficult aryl substitution to synthesize N-aryl substituted arylamide compounds, etc., and achieves high reaction selectivity and low cost. Low, economical effect

Inactive Publication Date: 2005-11-02
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These methods are difficult to be used in the synthesis of N-aryl substituted aromatic amides by aryl substitution on the N of the existing aromatic amides

Method used

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  • Process for synthesizing aryl substituted N-aryl amide compounds
  • Process for synthesizing aryl substituted N-aryl amide compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0016] In a 100mL stainless steel autoclave, add benzamide (15mmol), Se (0.5mmol), nitrobenzene (10mmol), DBU (10mmol), Et 3 N (10mmol) and toluene (10ml), after replacing three times with CO, raise the CO pressure to 3MPa, put it into an oil bath that has risen to 150°C and stir for 4 hours, cool to room temperature, open the kettle, and filter The resulting solid and mother liquor concentrate were separated and purified by column chromatography, the eluent was petroleum ether: ethyl acetate (7:3), the product was obtained by concentrating and removing the eluent, the product was N-phenylbenzamide, HPLC The analytical purity is above 99%, and the yield is 90.1%. The content determination adopts Waters high-performance liquid chromatography system, including two 515 pumps, 486 type UV detector, Spherisorb ODS-2 column (5μm, 4.6×250mm), using methanol-water as mobile phase, flow rate: 1mL / min, detection The wavelength of the detector is λmax of each compound, column temperatur...

Embodiment 2

[0018] The organic solvent is benzene, and the consumption is 10ml. Other experimental methods and conditions are the same as in Example 1. The HPLC analysis purity is more than 99%, and the actual yield is 75.4% (in terms of nitrobenzene).

Embodiment 3

[0020] The organic solvent was tetrahydrofuran, and the consumption was 10 ml. Other experimental methods and conditions were the same as in Example 1. The HPLC analysis purity was more than 99%, and the actual yield was 61.6% (in terms of nitrobenzene).

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Abstract

The present invention is synthesis process of N-aryl substituted aryl amide compound. Aryl amide and aromatic nitro compound are reacted in organic solvent inside high pressure reactor in the presence of CO with selenium as catalyst and DBU and triethylamine as co-catalyst, where, the substitutent on the aryl radical in the aromatic compound may be electron donor or acceptor group(s), the material molar ratio between aryl amide and aromatic nitro compound is 0.1-10, the molar consumption of selenium is 0.1-20 % of the less material, the molar consumption of triethylamine is 10-200 % of the less material, the molar ratio between the reactant and organic solvent is 0.02-1, the reaction period is 2-20 hr, reaction temperature is 50-200 deg.c, and CO pressure is 1-10 MPa gauge pressure. The present invention has simple operation, high selectivity, high yield, stable product quality and easy post separation.

Description

technical field [0001] The invention relates to a preparation method of N-aryl substituted aromatic amide compounds, in particular to a method for synthesizing N-aryl substituted aromatic amide compounds by catalytic reduction substitution reaction. Background technique [0002] N-aryl substituted aromatic amide compounds are an important class of fine chemicals, which can be directly used as pesticides and pharmaceuticals, and are also important intermediates of fine chemicals. Currently, methods for synthesizing such compounds include N-acylation, N-alkylation, C-acylation, addition, redox, and rearrangement reactions. Among them, the acylation reaction is widely used and researched deeply. N-acylation mainly has eight types of reactions: the first type is to use substituted benzoic acid and substituted arylamine for acylation reaction, and a molecule of water is removed to generate the target product; the second type is to use substituted benzoyl chloride and arylamine f...

Claims

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Application Information

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IPC IPC(8): C07C233/64
Inventor 梅建庭陈金铸凌冈陆世维
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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