Hydrochloric Acid → HCID 118059637, compound

Participants

Reaction Conditions

Reaction Steps

A solution of chlorosulfonylisocyanate (6.96 mL, 80 mmol) in dichloromethane (120 mL) was cooled to 0° C. 2,2,2-trichloroethanol (7.67 mL, 80.0 mmol, 1.0 equiv.) was added via addition funnel at 0° C. This mixture was stirred at 0° C. for 1.5 h. To this mixture was then added a solution of aminoacetaldehyde dimethyl acetal (8.76 mL, 80.0 mmol, 1.0 equiv.) and triethylamine (TEA, 33.4 mL, 240 mmol, 3.0 equiv.) in dichloromethane (DCM, 120.0 mL) added drop-wise via addition funnel at 0° C. The reaction was warmed to room temperature and stirred at room temperature overnight. The reaction was treated with 0.1 N hydrochloric acid and the collected organic phase was washed with brine, dried over Na2SO4, and concentrated to give the desired product (28.01 g, 97%) as a crude off-white solid, which was used in the subsequent reaction without further purification. 1H NMR (300 MHz, DMSO-d6) δ 11.79 (s, 1H), 8.08 (t, 1H, J=5.9 Hz), 4.90 (s, 2H), 4.37 (t, 1H, J=5.5 Hz), 3.23 (s, 6H), 3.00 (dd, 2H, J=5.7 Hz).

Provenance & Evidence