Premium
Synthesis of 14 C‐labelled polychlorobiphenyls derived from the labelled 4‐chloro‐, 2,5‐dichloro‐, 3,4‐dichloro‐, 2,3‐dichloro‐2,4,5‐trichloro‐ and 2,3,6‐trichloroanilines
Author(s) -
Bergman Å.,
Bamford I.,
Wachtmeister C. A.
Publication year - 1981
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580180713
Subject(s) - aniline , chemistry , acetanilide , medicinal chemistry , dichloromethane , benzene , chlorine , chloride , hydrolysis , nuclear chemistry , organic chemistry , solvent
[ 14 C] Aniline hydrogen sulphate was acetylated, and the acetanilide obtained was chlorinated with N‐chlorosuccinimide to 2‐chloro, 4‐chloro‐ and 2, 4‐dichloroacet[ 14 C] anilide. The labelled 2‐ and 4‐chloroacet[ 14 C] 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 [ 14 C] aniline. The labelled 2, 3‐dichloro‐ and 2,3, 6‐trichloroanilines were obtained as minor products from the chlorination of 2‐chloro [ 14 C] aniline, likewise 2,4, 5‐trichloroaniline was obtained from 4‐chloro [ 14 C] aniline. The [ 14 C] 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[ 14 C]biphenyl. 3, 4‐Dichloro [ 14 C] aniline and biphenyls prepared from this aniline were found to be contaminated by bromoanalogues. The origin of these have been studied.