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Synthesis 2010(7): 1113-1122  
DOI: 10.1055/s-0029-1219226
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Facile, Safe and Inexpensive Preparation of S-Methyl Arylcarbamothioates by Methylthiocarbonylation of Primary Arylamines with O,S-Dimethyl ­Carbonodithioate

Iacopo Degani, Rita Fochi*, Claudio Magistris
Dipartimento di Chimica Generale e Chimica Organica, Università degli Studi di Torino, C.so M. D"Azeglio 48, 10125 Torino, Italy
e-Mail: rita.fochi@unito.it;
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Publikationsverlauf

Received 19 November 2009
Publikationsdatum:
20. Januar 2010 (online)

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Abstract

O,S-Dimethyl carbonodithioate is proposed as a suitable and safely handled reagent that can be used in the methylthiocarbonylation of primary arylamines to give S-methyl arylcarbamothioates. Optimal conditions involved a one-step procedure that was carried out at 45 ˚C in a solvent-free system, in the presence of triethyl(methyl)ammonium S-methyl carbonodithioate as a reaction promoter. The title products were obtained pure in yields that, with one exception, varied between 72 and 91% (average yield of the 12 considered examples was 83%). The by-product S,S-dimethyl carbonodithioate is also a valuable reagent.

Key words

O,S-dimethyl carbonodithioate - arylcarbamothioates - thiocarbonylation - S,S-dimethyl carbonodithioate - toluene-2,4-dithiocarbamic acid S,S-dimethyl ester

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1

Professor Emeritus, University of Turin, Italy.

23

Oxon Italia S.p.A., 20016 Pero (Milano), Italy.