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

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Reaction Conditions

Reaction Steps

5-Bromo-2-methyl-2-pentene (25 g, 0.154 mol) was dissolved in dry dimethylformamide (DMF) (200 mL). To the solution was added K2CO3 (21.3 g, 0.154 mol) and 2-nitroimidazole (17.4 g, 0.154 mol). The mixture was stirred under N2 atmosphere at 75° C. for 48 hours. DMF was evaporated on a rotary evaporator. The yellow gummy residue was stirred with water (150 mL) to give yellow solid, which was dissolved in diethyl ether (150 mL), dried over Na2SO4 and evaporated on a rotary evaporator to yield the title product. Yield 27.8 g (92%). mp: 49-51° C. MS: (M+H)+=196, M+=195. 1H NMR (CDCl3) δ1.45 and 1.68 (s, 6H, gem-di-CH3), 2.52 (q, 2H, CH2CH═), 4.43 [t, 2H, CH2-(2-nitroimidazolyl)], 5.08 (t, 1H, CH2CH═), 7.05 and 7.14 (s, 2H, 2-nitroimidazolyl-H).

Provenance & Evidence