Water → tert-butyl N-(thiophen-3-yl)carbamate

Participants

Reaction Steps

Thiophene-3-carboxylic acid (2.50 g, 19.5 mmol), diphenylphosphoryl azide (4.62 mL, 21.5 mmol), triethylamine (3.26 mL, 23.4 mmol) were dissolved in tert-butanol (50 mL), and the solution was stirred for 3.5 hours under reflux. Water was added to the reaction solution at 0° C., which was then extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=10:1), and the title compound (3.33 g, 16.7 mmol, 86%) was obtained as a white solid.

Provenance & Evidence