[S:1]([C:5]1[S:9][C:8]([C:10]#[N:11])=[CH:7][CH:6]=1)(=[O:4])(=[O:3])[NH2:2].Cl.[NH2:13][OH:14].C(=O)([O-])[O-].[Na+].[Na+]>O.C(O)C>[OH:14][NH:13][C:10]([C:8]1[S:9][C:5]([S:1](=[O:4])(=[O:3])[NH2:2])=[CH:6][CH:7]=1)=[NH:11]A stirred mixture of 5-sulfamoyl-thiophene-2-carbonitrile [CAS-No. 519055-65-3] (0.31 g, 1.65 mmol), hydroxylamine hydrochloride (0.23 g, 3.31 mmol) and sodium carbonate (0.175 g, 1.65 mmol) in water (4.6 ml) and ethanol (1 ml) was heated under reflux conditions for 1.5 h. The reaction mixture was poured into water (50 ml) and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with brine (100 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography on silica gel (ethyl acetate/heptane) and crystallization (ethyl acetate/MeOH/hexane) to yield the title compound (0.21 g, 58%) as a white solid. MS (ISN) 220.1 [(M−H)−]; mp 189° C.
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