Hydrochloric Acid → N-(4-(((5-Methyl-1,3,4-thiadiazol-2-yl)amino)sulphonyl)phenyl)acetamide

Participants

Reaction Conditions

Reaction Steps

2-Amino-5-methyl-1,3,4-thiadiazole (250 mg, 2.19 mmol) was suspended in pyridine (0.5 mL). N-Acetylsulfanilyl chloride (410 mg, 1.75 mmol) was added slowly at 0° C. The reaction mixture was then heated to 95° C. and was stirred for 1 h. The reaction mixture was then added to aqueous 3N HCl and the mixture extracted with ethyl acetate. The organic extracts were washed with water (3×20 mL), brine (3×20 mL), dried over anhydrous Na2SO4, filtered, and volatiles evaporated. The residue was crystallized from MeOH to give the product (491 mg, 1.6 mmol, 97%) as a solid, mp 239-240° C.; 1H NMR (500 MHz, DMSO) δ 2.07 (3, s), 2.44 (3, s), 7.74 (4, s), 10.82 (1, s), 13.85 (1, s); 13C NMR (125 MHz, DMSO) δ 16.1, 24.1, 118.6, 126.9, 135.7, 142.8, 154.3, 167.7, 168.9; MS (ESI+, m/z) Calculated for C11H13N4O3S2 313.0. found 313.0 (M+H)+; HRMS (FAB+, m/z) Calculated for C11H13N4O3S2 313.0429. found 313.0428 (M+H)+.

Provenance & Evidence