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Monatshefte für Chemie / Chemical Monthly

, Volume 106, Issue 6, pp 1449–1460 | Cite as

Zur Kenntnis der Substitutionsprodukte der (2H)-Imidazol-4(3H)-thione und 2H-Imidazol-4(3H)-one

Über die gemeinsame Einwirkung von elementarem Schwefel und gasförmigem Ammoniak auf Ketone, 88. Mitt.
  • Friedrich Asinger
  • Alfons Saus
  • E. Fichtner
  • H. -J. Gräber
  • W. Leuchtenberger
Organische Chemie und Biochemie

Substitution products of 2H-imidazole-4(3H)-thiones and 2H-imidazol-4(3H)-ones. On the joint action of elemental sulfur and gaseous ammonia upon ketones, 88

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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Literatur

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Copyright information

© Springer-Verlag 1975

Authors and Affiliations

  • Friedrich Asinger
    • 1
  • Alfons Saus
    • 1
  • E. Fichtner
    • 1
  • H. -J. Gräber
    • 1
  • W. Leuchtenberger
    • 1
  1. 1.Institut für Technische Chemie und Petrolchemie der Rheinisch-Westfälischen Technischen Hochschule AachenAachenBundesrepublik

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