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Synthesis of 14 C‐labelled crotamiton
Author(s) -
Chaudhuri Naba K.,
Potdar Sudhakar V.,
Ball Thomas J.
Publication year - 1982
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.2580190110
Subject(s) - chemistry , sodium hydride , methyl iodide , iodide , medicinal chemistry , sodium iodide , iodine , organic chemistry
The synthesis of 14 C‐labelled crotamiton, which is a fungicide, an insecticide as well as a scabicide is described. Starting from 2‐bromonitrobenzene and Cu 14 CN, o ‐toluidine, labelled with 14 C at the methyl group was prepared by the following sequence of reactions: NO 2 ‐C 6 H 4 ‐Br → NO 2 ‐C 6 H 4 ‐ 14 CN → NO 2 ‐C 6 H 4 ‐ 14 COOH → NO 2 ‐C 6 H 4 ‐ 14 CH 2 OH → NO 2 ‐C 6 H 4 ‐ 14 CH 2 Br → NH 2 ‐C 6 H 4 ‐ 14 CH 3 . Labelled o ‐toluidine was then heated with crotonic anhydride to give crotonic acid o ‐toluidide which was then ethylated by treatment with sodium hydride and ethyl iodide to obtain labelled crotamiton.