Synthesis of Dichlorobenzamide Derivatives: Crystal Structures of 3,5-Dichloro-N-(2-chlorophenyl)benzamide and 3,5-Dichloro-N-(4-chlorophenyl)benzamide

Reactions of 3,5-dichlorobenzoyl chloride and arylamine compounds in N,N '-dimethylformamide solution at 60 degrees C afforded a series of dichlorobenzamide derivatives 4-14 in good yields. These new compounds and accompanying intermediates were characterized and confirmed by nuclear magnetic resonance and infrared spectroscopy, of which structures of compounds 4 and 6 were established by X-ray crystallography. Compound 4 crystallizes in triclinic space group Pi, with a = 5.047 (18), b = 10.28 (4), c = 13.36 (5) angstrom, alpha = 107.59 (5)degrees, beta = 93.55 (5)degrees, gamma = 98.34 (5)degrees, and Z = 2. The unit cell of 6 has a monoclinic Pn symmetry with the cell parameters a = 9.581 (3), b = 12.217 (4), c = 11.072 (3) angstrom, beta = 92.584 (4)degrees, and Z = 4. [GRAPHICS] . A series of 3,5-dichlorobenzamide compounds were synthesized from reactions of arylamine compounds with 3,5-dichlorobenzoyl chloride, which was prepared from 3,5-dichlorobenzonitrile.

Automated summary

Reactions of 3,5-dichlorobenzoyl chloride and arylamine compounds in N,N'-dimethylformamide solution at 60 degrees C led to the synthesis of a series of dichlorobenzamide derivatives 4-14, with compounds 4 and 6 having their structures confirmed by X-ray crystallography.