Hydrochloric Acid → 2-(5-(4-Aminophenylsulfonamido)-1,3,4-thiadiazol-2-yl)acetic Acid

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Reaction Steps

Distilled water (3.0 mL) and 10% aqueous NaOH (1.5 mL) were added to compound 118E (300 mg, 0.78 mmol) and the mixture was heated under reflux for 2 h. The pH of the solution was then adjusted to 4.0 by addition of 1.0 M HCl, the resulting precipitate was isolated by filtration, washed with cold water, and dried to give 201 mg (0.64 mmol, 82%) of the product as a solid, mp 209-210° C.; 1H NMR (600 MHz, DMSO-d6) δ 3.59 (s, 2H), 6.52 (d, 2H, J=8.1 Hz), 7.42 (d, 2H, J=8.9 Hz); 13C NMR (75 MHz, DMSO-d6) δ 36.6, 113.3, 127.8, 128.4, 152.4, 153.3, 167.7, 170.4; MS (LCQ, ESI+) Calcd for C10H11N4O4S2 315.0, found 315.0 (M+H)+; HRMS (ESI+, m/z) Calcd for C10H11N4O4S2 315.0222, found 315.0220 (M+H)+.

Provenance & Evidence