Alkylation of ethylenethiourea with alcohols: a convenient synthesis of S-alkyl-isothioureas without toxic alkylating agents

S-Alkyl isothioureas were obtained in high yields with alcohols replacing carcinogenic and toxic alkylating agents. The alkylation of ethylenethiourea with alcohols and aqueous acids (HCl, HBr, and HI) allows the synthesis of the respective S-alkyl-isothioureas in high yield and purity. Consistently...

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Bibliographic Details
Published in:Tetrahedron letters 2005-10, Vol.46 (44), p.7597-7599
Main Authors: Denk, Michael K., Ye, Xuan
Format: Article
Language:English
Subjects:
Alkylation
S-Alkyl-isothiourea
Thiourea
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Summary:S-Alkyl isothioureas were obtained in high yields with alcohols replacing carcinogenic and toxic alkylating agents. The alkylation of ethylenethiourea with alcohols and aqueous acids (HCl, HBr, and HI) allows the synthesis of the respective S-alkyl-isothioureas in high yield and purity. Consistently high yields (91–98%) were obtained with 56% HI, the yields for 48% HBr (48–93%) and 37% HCl (36–85%) were lower and varied with the type of alcohol. The method is a convenient low-cost alternative to the use of alkyl iodides and an easy access to the S- tert-butyl isothiourea.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.08.150