[Cl-].[OH:2][NH3+:3].C([O-])(=O)C.[Na+].[CH3:9][S:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=O)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1>O.C(O)C>[CH3:9][S:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[N:3][OH:2])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1Hydroxylammonium chloride (4.19 g, 60.2 mmol) and sodium acetate (7.42 g, 90.4 mmol) are dissolved in 20 ml of water. To this solution 9.72 g (40.1 mmol) of 1-(4-methylsulfanyl-phenyl)-2-phenyl-ethanone in 60 ml of ethanol are added. The reaction mixture is heated to reflux for 18.5 hr. The reaction mixture was concentrated by rotary evaporation and poured into water. The resulting white solid is filterd and washed with water. After drying under reduced pressure, recrystallization from hexane-CH2Cl2 affords 7.32 g of a white solid (71%). 1H NMR (CDCl3), δ[ppm]: d 2.45 (s, 3H), 4.20 (s, 2H), 7.16-7.20 (m, 3H), 7.24-7.27 (m, 4H), 7.54 (d, 2H), 9.03 (s, 1H).
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