hydroxylamine-O-sulfonic acid → (5-Bromo-1,3-thiazol-2-yl)methanesulfonamide

Participants

Reaction Steps

The product of Step 3 (1.244 g, 3.79 mmol) was taken up in THF (50 mL) at room temperature, and NaOMe (25% in MeOH, 0.819 g, 3.79 mmol) was added. After 30 min at room temperature, the suspension was evaporated to dryness, providing a yellow solid. The solid was taken up in water (25 mL), and a solution of NaOAc (1.710 g, 20.85 mmol) and hydroxylamine-O-sulfonic acid (2.143 g, 18.95 mmol) in water (12.5 mL) was added while cooling the reaction (0° C.). The reaction was vigorously stirred at room temperature overnight. The reaction was extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated. Flash chromatography (dry load, 10-100% EtOAc/hexanes) afforded 1-(5-bromo-1,3-thiazol-2-yl)methanesulfonamide (470 mg, 48%) as a colorless solid. MS ESI: [M+H]+ m/z 256.9/258.9.

Provenance & Evidence