FIELD: pharmacology.
SUBSTANCE: invention relates to a method for preparation of N1-[2-amino-4-(trifluoromethyl) phenyl]-N1phenyl-4-(trifluoromethyl)benzene-1,2-diamine and its derivatives of the general formula (I). The derived compounds can be used for synthesis of aromatic polyimides, finding application in various advanced technologies for semiconductor packages, electronic circuits, fuel cells, liquid crystal displays (LCD), for gas separation using polymeric membranes. Methods for preparation of N1-[2-amino-4-(trifluoromethyl)phenyl]-N1-phenyl-4-(trifluoromethyl)benzene-1,2-diamine and its derivatives of the general formula , where R=H, Br, Cl, F, CH3, includes a nucleophilic substitution of the chlorine atom in the 4-nitro-2-(trifluoromethyl)chlorobenzene when interacting with aniline or its corresponding derivative in solvent medium for 2.5 hours at 80°C and molar ratio of 2-nitro-4-(trifluoromethyl)chlorobenzene : 4-R-aniline = 2:1 and recovery of the resulting 2-nitro-N-[2-nitro-4-(trifluoromethyl)phenyl]-N-(4-(R)-phenyl)-4-(trifluoromethyl)aniline. Here, nucleophilic substitution is carried out by ultrasound in DMSO as the organic solvent, in the presence of tributylamine. Recovery of 2-itro-N-[2-nitro-4-(trifluoromethyl)phenyl]-N-(4-(R)-phenyl)-4-(trifluoromethyl)anilines is performed in a mixture of alcohol and 9% hydrochloric acid in volumetric ratio of 1:1, using electric current in a diaphragm cell in galvano-static mode in the presence of TiCl3, taken in the molar ratio of catalyst-carrier: dinitrosubstrate of 0.05:1, at a temperature of 40°C on lead cathode, while a passing a charge 12 F for 0.6 h through electrolytic cell, at current density of 9.45 A/dm2, 10% solution of sulfuric acid is used as the anolyte, platinum is used as the anode. The desired product is isolated.
EFFECT: method allows to obtain products with a high yield in a shorter time, carry out a nucleophilic substitution reaction in homogeneous conditions and is more economical sue to elimination of expensive agents and reduced amount of harmful waste.
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Authors
Dates
2018-03-01—Published
2016-06-29—Filed