Hydrochloric Acid → 4-chloro-4-methyl-1-(2-nitro-1H-imidazol-1-yl)-3-nitrosopentane

Participants

Reaction Conditions

Reaction Steps

4-Methyl-1-(2-nitro-1H-imidazol-1-yl)-3-pentene (8 g, 41 mmol) was dissolved in isoamyl nitrite (50 mL) at room temperature. The solution was cooled to 0° C. in an ice-salt bath and concentrated HCl (12 mL) was added dropwise. The reaction temperature was maintained between 3-5° C. during the HCl addition; the reaction was stirred in an ice-salt bath for 45 minutes after the addition of HCl. The product was filtered, washed with ethanol-ether (1:2) and dried in vacuum to give 8.6 g (81%) of the title product as a white solid; mp: 96-97° C. MS: (M+H)+=261, M+=260. 1H NMR (DMSO-d6) δ 1.70 (s, 6H, gem-di-CH3), 2.94 (t, 2H, CH2C═NOH), 4.65 [t, 2H, CH2-(2-nitroimidazole)], 7.16 and 7.52 (s, 2H, 2-nitroimidazolyl-H), 11.43 (s, 1H, CH2C═NOH).

Provenance & Evidence