An Updated Synthesis of the Diazo-Transfer Reagent Imidazole-1-sulfonyl Azide Hydrogen Sulfate

J Org Chem. 2016 Apr 15;81(8):3443-6. doi: 10.1021/acs.joc.6b00177. Epub 2016 Mar 29.

Abstract

Imidazole-1-sulfonyl azide and salts thereof are valuable reagents for diazo-transfer reactions, most particularly conversion of primary amines to azides. The parent reagent and its HCl salt present stability and detonation risks, but the hydrogen sulfate salt is significantly more stable. An updated procedure for the large-scale synthesis of this salt avoids isolation or concentration of the parent compound or HCl salt and will facilitate the use of hydrogen sulfate salt as the reagent of choice for diazo transfer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aza Compounds / chemical synthesis*
  • Aza Compounds / chemistry
  • Azides / chemical synthesis*
  • Azides / chemistry
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Indicators and Reagents / chemical synthesis*
  • Indicators and Reagents / chemistry
  • Molecular Structure
  • Sulfones / chemical synthesis*
  • Sulfones / chemistry

Substances

  • Aza Compounds
  • Azides
  • Imidazoles
  • Indicators and Reagents
  • Sulfones
  • imidazole-1-sulfonyl azide