A convenient method for the preparation of primary and symmetrical N,N '-disubstituted thioureas

A convenient process for the preparation of both primary thioureas 2 and symmetrical N,N'-disubstituted thioureas 6 based on the condensation of amine hydrohalides 5 with potassium thiocyanate has been developed. This approach tolerates sterically bulky primary amine substrates (both chiral and...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 11; pp. 1569 - 1574
Main Authors Herr, RJ, Kuhler, JL, Meckler, H, Opalka, CJ
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 2000
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACID
ANTAGONIST
amine hydrohalide
symmetrical thioureas
ANALOGS
REVERSE-TRANSCRIPTASE
SULFONAMIDES
potassium thiocyanate
POTENT
primary thioureas
CHEMISTRY
INHIBITORS
DERIVATIVES
CAPSAICIN
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Summary:A convenient process for the preparation of both primary thioureas 2 and symmetrical N,N'-disubstituted thioureas 6 based on the condensation of amine hydrohalides 5 with potassium thiocyanate has been developed. This approach tolerates sterically bulky primary amine substrates (both chiral and achiral), and the products can usually be isolated by a simple filtration of the reaction mixture. This method is an especially attractive alternative for the synthesis of thioureas when the corresponding isothiocyanates are unavailable, or difficult to prepare. It is also worth noting that a wide variety of amine hydrohalides, which are used in this procedure, are commercially available.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2000-7607