Hydrochloric Acid → B-[3-(1,3,4-Thiadiazol-2-ylamino)phenyl]boronic acid

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Reaction Steps

LiOH (340 mg, 14 mmol) was added to a stirred solution of Potassium [3-([1,3,4]Thiadiazol-2-ylamino)-phenyl]trifluoroborate (1.15 g, 4 mmol) in CH3CN (20 ml) and H2O (10 ml) at RT. The reaction was stirred at RT for 20 hours. The mixture was treated with saturated aqueous NH4Cl (32 ml) and 2N HCl (5 ml) to give ˜pH5. EtOAc was added and the precipitate was collected by filtration. The aqueous layer was extracted with CH2Cl2 (×2). The combined extracts were evaporated and the residue was combined with the solid from above. This material was suspended in EtOAc. The solid was collected by filtration and then dried to give the title compound (1.1 g) beige solid. 1H NMR (400 MHz, DMSO-d6) mixture, possibly of the boronic acid and cyclic species. This material was used without further purification.

Provenance & Evidence