[CH3:1][C:2]1[C:3]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)=[N:4][S:5][N:6]=1.Cl.[NH2:16][OH:17]>N1C=CC=CC=1>[OH:17][N:16]=[C:7]([C:3]1[C:2]([CH3:1])=[N:6][S:5][N:4]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1To a stirred solution of (4-Methyl-[1,2,5]thiadiazol-3-yl)-phenyl-methanone (20 g, 98 mmol) in dry pyridine (70 mL) was added hydroxylamine hydrochloride (17 g, 245 mmol). The reaction mixture was stirred at 70° C. for 3 h, then concentrated in vacuo and diluted with ethyl acetate (100 mL) and water (100 mL). The organic layer was washed with water (2×100 mL) and dried over MgSO4. Evaporation of the solvent in vacuo afforded N-hydroxy-1-(4-methyl-1,2,5-thiadiazol-3-yl)-1-phenylmethanimine as an orange oil [24.3 g, yield 99.6%; HPLC/MS: m/z=220 (M+H); log P(HCOOH)=2.26].
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