tert-Butanol → tert-butyl N-(1,3-thiazol-4-yl)carbamate

Participants

Reaction Steps

5.80 ml (41.84 mmol) of triethylamine and subsequently, with ice-bath cooling, 9.10 ml (42.19 mmol) of diphenyl azidophosphate are introduced into a solution of 4.85 g (37.55 mmol) of 4-thiazolecarboxylic acid in 180 ml of tert-butanol under nitrogen, and the reaction mixture is heated under reflux for 16 h. The solvent is removed in vacuo, the residue is taken up in dichloromethane and washed twice with water and saturated NaCl solution. The organic phase is dried over sodium sulfate, evaporated in vacuo, and the residue is purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1/1), giving 7.07 g (35.30 mmol, 94%) of tert-butyl N-(1,3-thiazol-4-yl)carbamate as beige crystals; ESI-MS: m/e: 201 ([M+H]+).

Provenance & Evidence