Diisopropylethylamine → N-(4-Methylpent-3-en-1-yl)-2-nitroimidazole

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Reaction Steps

To a mixture of 7-amino-4-aza-3,3-dimethyl-5-oxaheptan-2-one oxime (Example 7(E), 0.875 g, 0.005 mol) and diisopropylethylamine (0.7 g, 0.0055 mol) was added 4-chloro-4-methyl-1-(2-nitro-1H-imidazol-1-yl)-3-nitrosopentane (Example 10(A), 1.3 g, 0.05 mol) and the mixture was stirred at room temperature for 24 hrs. The white solid formed was filtered and dried. This was purified by column chromatography (silica gel, CH2Cl2 :CH3OH) followed by recrystallization from acetonitrile. mp 122°-123° C. 1H NMR (D2O)ε 1.16 [s, 6H, C(CH3)2 ], 1.36 [s, 6H, C(CH3)2 ], 1.81 (s, 3H, CH3), 2.87 (t, 2H, CH2CH2CN<), 3.11 (m, 2H, OCH2CH2NH), 3.86 (m, 2H,OCH2CH2NH), 4.69 (t, 2H, CH2CH2CN<), 7.10 and 7.36 (s, 2H, imiH). Anal. Calcd. for C16H29N7O5 : Found: C, 48.47; H, 7.39; N, 24.12. Calcd.: C, 48.11; H, 7.32; N, 24.55.

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