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Synthesis of N-(Mercaptomethyl)-Phthalimide-Carbonyl-14C-S-(O,O-Dimethylphosphorodithioate)

✍ Scribed by M. A. Leaffer; W. A. Skinner; J. J. Menn; J. B. McBain; L. W. Fancher

Publisher
John Wiley and Sons
Year
1967
Tongue
French
Weight
245 KB
Volume
3
Category
Article
ISSN
0022-2135

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✦ Synopsis

N -(mercaptomethyl) -phthalimide-carbonyl-14C-S-(0,O-

Dimethylphosphorodithioate)

has been synthesized. The starting material was carboxyl labelled o-toluic acid which was oxidized to o-phthalic acid. Phthalimide (carbonyl-W) was prepared from o-pkthalic acid by subliming the ammonium salt of the acid. When 14C 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.

INTRODUCTION.

The biological activity of N-(Mercaptolhethy1)phthalimide-S-(0,O-dimethylphosphorodithioate) (VI) was reviewed in a paper by Menn et al. (l). Studies on the metabolism of VI were conducted in plants by Menn and McBain (8), in rats by Ford et al. (3), in a steer by Chamberlain (4) and in This paper reports the synthesis of VI labeled with I4C in one of the insects by Menn et al. ( 5 ) . k. 4 carbonyl groups.

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