Hydrochloric Acid → Ethyl 5-(4-Acetamidophenylsulfonamido)-1,3,4-thiadiazole-2-carboxylate

Participants

Reaction Steps

To a solution of p-acetamidobenzenesulfonyl chloride (1.98 g, 8.47 mmol) in pyridine (20 mL) was added ethyl 5-amino-1,3,4-thiadiazole-2-carboxylate (1.2 g, 7.06 mmol). The reaction mixture was stirred at room temperature for 4.5 h, than 2 M HCl (50 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (3×60 mL). The organic extracts were washed with water (50 mL), brine (50 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography on silica gel (70-230 mesh) eluted with CH2Cl2:methanol 19:1 to give the product as a solid, mp 201-202° C., in 73% yield (1.91 g, 5.15 mmol); 1H NMR (300 MHz, DMSO-d6) δ 1.29 (t, 3H, J=6.9 Hz), 2.08 (s, 3H), 4.37 (q, 2H, J=7.8 Hz), 7.74 (m, 4H), 10.32 (s, 1H); 13C NMR (75 MHz, DMSO-d6) δ 13.9, 14.0, 24.1, 62.9, 118.6, 127.1, 134.9, 143.2, 147.2, 157.5, 167.6, 169.0; MS (LCQ, ESI+) Calcd for C13H15N4O5S2 371.0. found 371.0 (M+H)+. HRMS (ESI+, m/z) Calcd for C13H15N4O5S2 371.0484. found 371.0472 (M+H)+.

Provenance & Evidence