Hydrochloric Acid → N-(4-(N-(5-(hydroxymethyl)-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)acetamide

Participants

Reaction Steps

To a solution of p-acetamidobenzenesulfonyl chloride (510 mg, 2.18 mmol) in pyridine (6 mL) was added 2-amino-5-hydroxymethyl-1,3,4-thiadiazole (260 mg, 1.98 mmol). The reaction mixture was stirred at room temperature for 4.5 h, then 2 M HCl (20 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (4×50 mL). The organic extracts were washed with water (40 mL), brine (40 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography on silica gel (70-230 mesh) eluted with CH2Cl2:methanol 9:1 to give the product as a solid, mp 101-102° C., in 82% yield (533 mg, 1.62 mmol); 1H NMR (300 MHz, DMSO-d6) δ 2.07 (s, 3H), 4.56 (d, 2H, J=5.1 Hz), 6.09 (t, 1H, J=4.8 Hz), 7.73 (m, 4H); 13C NMR (75 MHz, DMSO-d6) δ 24.8, 59.1, 119.3, 127.7, 136.2, 143.5, 161.7, 168.1, 169.6; MS (LCQ, ESI+) Calcd for C11H13N4O4S2 329.0. found 329.1 (M+H)+. HRMS (ESI+, m/z) Calcd for C11H13N4O4S2 329.0378. found 329.0376 (M+H)+.

Provenance & Evidence