O.O.[CH3:3][C:4]1[N:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[N:5]=1.C(CC(=O)C)(=O)C.Cl.C(N)(=[NH:22])C.[C:24]1([CH3:37])[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([CH3:31])[C:25]=1[S:32]([O:35]N)(=[O:34])=[O:33]>ClCCl>[C:24]1([CH3:37])[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([CH3:31])[C:25]=1[S:32]([O-:35])(=[O:34])=[O:33].[NH2:22][N+:5]1[C:6]([CH3:11])=[CH:7][C:8]([CH3:10])=[N:9][C:4]=1[CH3:3]2,4,6-trimethylpyrimidine dihydrate (0.79 g, 5.0 mmole, prepared from acetylacetone and acetamidine hydrochloride according to A. Bowman, J. Chem. Soc. 1937;494–495) in dichloromethane (10 mL) was dried over Na2SO4 and filtered. Separately, O-(mesitylenesulfonyl)hydroxylamine containing ca. 25% water (1.57 g, ca. 5.4 mmole) was dissolved in dichloromethane (10 mL) and dried over Na2SO4 and filtered. The dry O-(mesitylenesulfonyl)hydroxylamine filtrate was added dropwise to the dry 2,4,6-trimethylpyrimidine filtrate at 0 C. Stirring was continued 5 hr at 0 C and then 16 hr at 4 C. The reaction mixture was concentrated at reduced pressure to ca. 10 mL and treated with ca. 3 mL ether to cause separation of a white powder, which was filtered, washed with 10 mL 1:1 dichloromethane/ether, and dried to yield 1.27 of crude product in two crops. Recrystallization from methanol/dichloromethane/ether gave 1.18 g of the title compound, mp 183–185 C.
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