Lawesson's reagent → tert-Butyl (1-carbamothioylcyclopropyl)carbamate

Participants

Reaction Steps

To a suspension of (1-carbamoyl-cyclopropyl)-carbamic acid tert-butyl ester (1.00 g, 4.99 mmol) in 6 mL of THF was added Lawesson's reagent (1.01 g, 2.50 mmol). The pale yellow cloudy reaction mixture was stirred at room temperature for 6 h and then partitioned between 40 mL of ethyl acetate and 15 mL of 0.5 M NaOH solution. The organic phase was washed with 15 mL each of water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude was purified by flash chromatography on silica gel, eluting with 20-60% EtOAc/hexanes, to give 864 mg (80%) of (1-thiocarbamoyl-cyclopropyl)-carbamic acid tert-butyl ester as a white solid.

Provenance & Evidence