Ammonium Chloride → HCID 86689233, compound

Participants

Reaction Steps

A mixture of 5-amino-3-(3-nitrophenyl)isothiazole-4-carboxamide (150 mg, 0.57 mmol), 0.5 mL saturated aqueous NH4Cl, and catalytic Zn powder in 6 mL MeOH was rapidly stirred at rt. After 1.5 hours additional saturated aqueous NH4Cl and catalytic Zn powder was added several times to push the reaction to completion. At 20 hours the reaction was heated at 55° C. for 6 hours, then stirred overnight at rt. The reaction was filtered using Celite and the solids rinsed with MeOH, the filtrate evaporated and treated to an aqueous workup using EtOAc and aqueous Na2CO3 to give a pale yellow solid. The solid was triturated with EtOAc/hexane to give 94 mg of faint yellow solid. Then the filtrate lot and the 94 mg of solid were separately chromatographed eluting with hexane/acetone and combined to give the title compound as an off-white solid (96 mg, 72%).

Provenance & Evidence