[CH3:1][I:2].[N+]1([O-])C=CNC=1.C(N1C[N:20]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:19][N:18]([CH2:29][C:30]2[CH:35]=CC=CC=2)C1)C1C=CC=CC=1.CC(=NO)[C:38](=[O:40])C>C(Cl)(Cl)Cl>[I-:2].[CH2:22]([N:20]1[C:30]([CH3:35])=[C:29]([CH3:1])[N+:18]([O:40][CH3:38])=[CH:19]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1
Methyl iodide (0.5 mL, 7.8 mmol) was added via syringe to a solution of imidazole-N-oxide 1 (1.0 g, 4.9 mmol) in ca. 20 mL of CHCl3 (compound 1 was prepared from 1,3,5-tribenzyl-[1,3,5]triazinane and butane-2,3-dione monooxime using the procedure of Arduengo et al. (1992), supra.) The resulting mixture was stirred at room temperature overnight. Removal of the volatiles in vacuo afforded a thick yellow oil of suitable purity in an undetermined yield. 1H-NMR (δ, CDCl3): 10.32 (s, 1H, N—CH—N); 7.39 (m, 5H, C6H5); 5.56 (s, 2H, NCH2); 4.38 (s, 3H, OCH3); 2.27 (s, 3H, CH3); 2.20 (s, 3H, CH3).
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