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Zur Kenntnis der Substitutionsprodukte der (2H)-Imidazol-4(3H)-thione und 2H-Imidazol-4(3H)-one
Authors:Prof. Dr. Friedrich Asinger  Alfons Saus  E. Fichtner  H. -J. Gräber  W. Leuchtenberger
Affiliation:1. Institut für Technische Chemie und Petrolchemie der Rheinisch-Westf?lischen Technischen Hochschule Aachen, Alte Maastrichter Stra?e 2, D-5100, Aachen, Bundesrepublik
Abstract:2H-Imidazole-4(3H)-thiones (a), available from methyl alkyl and methyl aryl ketones with sulfur and ammonia, react via their corresponding N-sodium compounds or in presence of tert. amines with alkyl and aryl carboxylic acid chlorides to give the corresponding intensely coloured (orange to violett) cryst. 3-acyl-2H-imidazole-4(3H)-thiones4 a-q and6–26. With dicarboxylic acid dichlorides the colourless cryst. N,N′-diacyl-bis-3-imidazoline-5-thiones5 a-d and27–32 are obtained. With carbamic acid chlorides and chloroformic acid esters the corresponding urea (33–35) and urethane derivatives36, 37 are formed. In an analogous way 2H-imidazol-4(3H)-ones react with acid chlorides to 3-acyl-2-imidazol-4(3H)-ones (44–50), which can also be obtained by treating the corresponding 3-acyl-2H-imidazole-4(3H)-thione with KMnO4.
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