Pyridine → 1,1-Dimethylethyl N-(aminosulfonyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To chlorosulfonyl isocyanate (2.45 mL, 28 mmol) in toluene (38 mL) at −10° C. (ice/methanol bath) was added t-butyl alcohol (2.66 mL, 28 mmol) dropwise. The resulting solution was stirred at 0° C. (ice bath) for 20 min. Pyridine (5.0 mL, 62 mmol) was added dropwise with the ice/methanol bath at −15° C. to −10° C. The resulting mixture was stirred with ice bath at 0° C. for 40 min. Ammonium hydroxide (28%, 10 mL, 163 mmol) was then added dropwise with the ice/methanol bath at −10° C., followed by H2O (3 mL). The resulting mixture resulting was stirred with ice bath at 0° C. for 2.5 h. The resulting two layers were separated. The aqueous layer was washed with toluene (15 mL). The combined toluene layers were extracted with H2O (13 mL). The combined aqueous layers were acidified with 24% H2SO4 to pH 2. The resulting precipitate was filtered, washed with H2O (2×13 mL) and dried to yield the title compound as a white solid.

Provenance & Evidence