Reactions of hexachloroacetone with primary diamines: Synthesis and characterization of N,N'-ethylenebistrichloroacetamide

CHED 317

Jin Bakalis, jshin@qcc.cuny.edu and Jun H. Shin, jshin@qcc.cuny.edu. Department of Chemistry, Queensborough Community College, 222-05, 56th Avenue, S-445, Bayside, NY 11364
The reaction of hexachloroacetone (HCA) with ethylenediamine gave N,N'-ethylenebistrichloroacetamide as a white solid at room temperature in high yield. The molecular structure of the white solid has been determined by X-ray diffraction, confirming that the ethylene group is bridging two trichloroacetamido units. The same reactivity was also observed with aromatic amines such as aniline and phenylenediamines as well as hexamethylenediamine. For example, a reaction between HCA and aniline gave N-phenyltrichloroacetamide at 80°C.