Unprecedented "In Water" imidazole carbonylation: paradigm shift for preparation of urea and carbamate

Org Lett. 2012 Jun 1;14(11):2814-7. doi: 10.1021/ol301009d. Epub 2012 May 18.

Abstract

The first "In Water" imidazolecarbonylation of amine is described. A one pot reaction of carbonylimidazolide in water with a nucleophile provides an efficient and general method for the preparation of urea, carbamates and thiocarbamates. Use of an anhydrous solvent and an inert atmosphere could be avoided. Product precipitate out from the reaction mixture and can be obtained in high purity by filtration, resulting in a simple and scalable method.

MeSH terms

  • Amines / chemistry*
  • Carbamates / chemical synthesis*
  • Carbamates / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Imidazoles / chemistry*
  • Molecular Structure
  • Thiocarbamates / chemical synthesis*
  • Thiocarbamates / chemistry
  • Urea / analogs & derivatives*
  • Urea / chemical synthesis*
  • Urea / chemistry
  • Water / chemistry*

Substances

  • Amines
  • Carbamates
  • Imidazoles
  • Thiocarbamates
  • Water
  • Urea