SYNTHESIS OF C-14-LABELED POLYCHLOROBIPHENYLS DERIVED FROM THE LABELED 4-CHLORO-ANILINES, 2,5-DICHLORO-ANILINES, 3,4-DICHLORO-ANILINES, 2,3-DICHLORO-ANILINES, 2,4,5-TRICHLORO-ANILINES, AND 2,3,6-TRICHLOROANILINES
[14C] Aniline hydrogen sulphate was acetylated, and the acetanilide obtained was chlorinated with Nâchlorosuccinimide to 2âchloro, 4âchloroâ and 2, 4âdichloroacet[14C] anilide. The labelled 2â and 4âchloroacet[14C] anilides were hydrolyzed and treated with aluminium chloride, hydrogen chloride and chlorine in dry dichloromethane to give the major products 2, 5âdichloroâ and 3, 4âdichloro [14C] aniline. The labelled 2, 3âdichloroâ and 2,3, 6âtrichloroanilines were obtained as minor products from the chlorination of 2âchloro [14C] aniline, likewise 2,4, 5âtrichloroaniline was obtained from 4âchloro [14C] aniline. The [14C] anilines prepared were coupled with benzene, 1, 4âdichloroâ, 1, 2âdichloro or 1, 3âdichlorobenzene to give 4âchloroâ, 2, 3â²,4â², 5âtetrachloroâ, 2, 3, 3â², 4â² â tetrachloroâ, 3,3â², 4,4â²âtetrachloroâ, 2, 2â², 5,5â²âtetrachloroâ, 2, 2â², 3,3â²âtetrachloroâ, 2, 2â², 3, 5â², 6âpentachloroâ, 2, 2â², 4, 4â², 5âpentachloroâ and 2, 3â²,4, 5, 5â²âpentachloro[14C]biphenyl. 3, 4âDichloro [14C] aniline and biphenyls prepared from this aniline were found to be contaminated by bromoanalogues. The origin of these have been studied. Copyright © 1981 John Wiley & Sons, Ltd.
radioisotope; 2,3,6 trichloroaniline c 14; 2,4,5 trichloroaniline c 14; 4 chloroaniline c 14; dichloroaniline c 14; drug analysis; drug synthesis; gas chromatography; in vitro study; liquid chromatography; mass spectrometry; polychlorinated biphenyl c 14; theoretical study; thin layer chromatography