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Synthesis of N‐(Mercaptomethyl)‐Phthalimide‐Carbonyl‐ 14 C‐S‐( O,O ‐Dimethylphosphorodithioate)
Author(s) -
Leaffer M. A.,
Skinner W. A.,
Menn J. J.,
McBain J. B.,
Fancher L. W.
Publication year - 1967
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590030406
Subject(s) - phthalimide , phthalic acid , chemistry , aqueous solution , thionyl chloride , hydroxymethyl , medicinal chemistry , ammonium chloride , nuclear chemistry , formaldehyde , organic chemistry , chloride , polymer chemistry
N‐ (mercaptomethyl) ‐phthalimide‐carbonyl‐ 14 C‐S‐ (O,O‐Dimethylphosphorodithioate) has been synthesized. The starting material was carboxyl labelled o‐toluic acid which was oxidized to o‐phthalic acid. Phthalimide (carbonyl‐ 14 C) was prepared from o‐phthalic acid by subliming the ammonium salt of the acid. When 14 C phthalimide was reacted with aqueous formaldehyde, N‐hydroxymethyl phthalimide was formed. The final product was obtained when the N‐hydroxymethyl derivative was reacted with thionyl chloride, followed by reaction with sodium dimethyl phosphorodithioate.