Premium
Labelled organophosphorus pesticides. III. Synthesis of carbon‐14 labelled o‐(2,6‐dichloro‐4‐methylphenyl) O,O‐dlmethyl phosphorothioate
Author(s) -
Yoshitake Akira,
Kanamaru Hiroshi,
Shono Fumiaki,
Nakatsuka Iwao
Publication year - 1979
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.2580160314
Subject(s) - chemistry , phenol , yield (engineering) , catalysis , aryl , medicinal chemistry , potassium cyanide , cyanide , organic chemistry , chlorine , carbon 14 , ring (chemistry) , potassium , alkyl , materials science , physics , quantum mechanics , metallurgy
O‐ (2,6‐Dichloro‐4‐methylphenyl) O,O‐dimethyl phosphorothioate (5‐3349) ( 1 ), a fungicide in soil, was labelled with carbon‐14 individually at the aryl methyl and the phenyl ring for use in metabolic studies. The synthetic procedures are illustrated in Fig. 1. 4‐Cyano‐ 14 C‐phenol was quantitatively converted to 4‐methyl‐ 14 C‐Phenol ( 3a ) by catalytic hydrogenation using 10% Pd‐C as a catalyst. Dichlorination of 3a with chlorine gave 2,6‐di‐chloro‐4‐methyl‐ 14 C‐phenol ( 4a ). Condensation of 4a with O,O‐dimethyl phosphorochloridothioate gave S‐3349‐(aryl methyl‐ 14 C) ( 1a ) in the overall yield of 22% from potassium cyanide‐ 14 C. By the similar procedures, 4‐methylphenol‐ 14 C 6 ( 3b ) was converted to S‐3349‐(Phenyl‐ 14 C 6 ) ( 1b ) in 70% yield.