Dimethylformamide → HCID 67062707, compound

Participants

Reaction Steps

To a stirred solution of 5-chloro-1,2,4-thiadiazol-3-amine (0.93 g, 6.9 mmol) and BOC2O (2.9 mL, 12 mmol) in DMF (10 mL, 129 mmol) was added sodium hydride (60%) (0.55 g, 14 mmol) at 0° C., and the resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was carefully diluted with aqueous NH4Cl and water (20 mL each) and diluted with EtOAc (15 mL). The separated aqueous layer was extracted with EtOAc (15 mL×2) and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give a residue which was purified with flash column chromatography (ISCO Combiflash system, pure hexanes→10% EtOAc in hexanes) to obtain the desired product (0.87 g, 54%) as an off-white solid. LCMS (API-ES) m/z (%): 180.6 (100%, (M++H)-tert-Bu); 1H NMR (400 MHz, CD3OD) δ ppm (1.55, s, 9H).\

Provenance & Evidence