tert-Butanol → tert-butyl N-(chlorosulfonyl)carbamate

Participants

Reaction Steps

To a stirred solution of chlorosulfonyl isocyanate (3.20 mL, 36.0 mmol) in benzene (15.0 mL) in a water bath at rt was added tert-butyl alcohol (3.50 mL, 36.2 mmol) dropwise via syringe under an atmosphere of nitrogen. After 2 h, the mixture was diluted with hexanes (30.0 mL) and the resulting white precipitate was filtered and washed with hexanes (3×20 mL). The collected solid was dried in a vacuum desiccator under house vacuum for 10 min to afford the title compound as a white solid (5.08 g, 65%). The product was stored under nitrogen in a freezer. 1H NMR (300 MHz, CDCl3, δ): 8.44 (br s, 1H), 1.57 (s, 9H) ppm. LC/MS: Rt=0.939 min, ES+ 215 (AA standard). Reference: F. Hirayama et al., Biorg. Med. Chem., 2002, 10, 1509-1523.

Provenance & Evidence