Synthesis

Preparation of mono-, di-, and trisubstituted ureas by carbonylation of aliphatic amines with S, S-dimethyl dithiocarbonate

E Artuso, I Degani, R Fochi, C Magistris

Index: Artuso, Emma; Degani, Iacopo; Fochi, Rita; Magistris, Claudio Synthesis, 2007 , # 22 p. 3497 - 3506

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Citation Number: 29

Abstract

Abstract General procedures are reported to prepare N-alkylureas, N, N′-dialkylureas (both symmetrical and unsymmetrical), and N, N, N′-trialkylureas by carbonylation of aliphatic amines, employing S, S-dimethyl dithiocarbonate (DMDTC) as a phosgene substitute. All reactions were carried out in water. Symmetrical disubstituted ureas were prepared directly working at 60 C with a molar ratio of DMDTC: amine= 1: 2, preferably under nitrogen. ...

~85%

~96%

~94%

~94%

~84%

~95%

~98%

~97%

~89%

~92%

Conversion of carbonimidodithioates to carbamates

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Geometrical isomerism in the S-alkyl thiohydroximate series:...

[Davies,J.H. et al. Journal of the Chemical Society [Section] C: Organic, 1968 , p. 431 - 435]