Ammonium Chloride → HCID 71621924, compound

Participants

Reaction Steps

A mixture of 5-amino-3-(4-nitrophenyl)isothiazole-4-carboxamide (63 mg, 0.24 mmol), 12 drops saturated aqueous NH4Cl, and catalytic Zn powder in 4 mL MeOH was rapidly stirred at rt. After 1.5 hours additional saturated aqueous NH4Cl (6 drops) and catalytic Zn powder was added and the reaction heated at 55° C. Then additional solid NH4Cl and catalytic Zn powder was added to push the reaction to completion. At 4 hours the reaction was filtered using Celite and the solids rinsed with MeOH and EtOAc, the filtrate evaporated and treated to an aqueous workup using EtOAc and saturated aqueous NaHCO3 to give a yellow gummy solid. This material was triturated with 20% EtOAc/hexane to give the title compound as a yellow-beige solid (53 mg, 94%).

Provenance & Evidence