A. Bergman, I. Bamford, C. Wachtmeister
Jul 1, 1981
Citations
0
Influential Citations
8
Citations
Journal
Journal of Labelled Compounds and Radiopharmaceuticals
Abstract
[14C] Aniline hydrogen sulphate was acetylated, and the acetanilide obtained was chlorinated with N-chlorosuccinimide to 2-chloro, 4-chloro- and 2, 4-dichloroacet[14C] anilide. The labelled 2- and 4-chloroacet[14C] anilides were hydrolyzed and treated with aluminium chloride, hydrogen chloride and chlorine in dry dichloromethane to give the major products 2, 5-dichloro- and 3, 4-dichloro [14C] aniline. The labelled 2, 3-dichloro- and 2,3, 6-trichloroanilines were obtained as minor products from the chlorination of 2-chloro [14C] aniline, likewise 2,4, 5-trichloroaniline was obtained from 4-chloro [14C] aniline. The [14C] anilines prepared were coupled with benzene, 1, 4-dichloro-, 1, 2-dichloro or 1, 3-dichlorobenzene to give 4-chloro-, 2, 3′,4′, 5-tetrachloro-, 2, 3, 3′, 4′ - tetrachloro-, 3,3′, 4,4′-tetrachloro-, 2, 2′, 5,5′-tetrachloro-, 2, 2′, 3,3′-tetrachloro-, 2, 2′, 3, 5′, 6-pentachloro-, 2, 2′, 4, 4′, 5-pentachloro- and 2, 3′,4, 5, 5′-pentachloro[14C]biphenyl. 3, 4-Dichloro [14C] aniline and biphenyls prepared from this aniline were found to be contaminated by bromoanalogues. The origin of these have been studied.