Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=3)[C:17](=[O:30])[CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[ClH:31].[NH2:32][OH:33].C(=O)([O-])O.[Na+]>C(O)C>[Cl:31][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([C:28](=[NH:29])[NH:32][OH:33])=[CH:26][CH:27]=3)[C:17](=[O:30])[CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2A mixture of 4-(6-chloronaphthalene-2-sulfonyl)-1-(4-cyanobenzyl)-2-piperazinone (440 mg), hydroxylamine hydrochloride (347 mg), sodium hydrogen carbonate (420 mg) and 80% ethanol (30 ml) was refluxed for 2 hours, and ethanol was evaporated. Precipitated crystals were washed with water, ethanol and ethyl acetate, and dried to give colorless crystals of the title compound (353 mg).
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