Water → 1-(3-Phthalimido-2-hydroxy propyl)-2-nitroimidazole

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Reaction Steps

To a solution of N-(2,3-epoxypropyl)phthalimide (commercially available, 20.3 g, 0.1 mol) in ethanol (200 mL), 2-nitroimidazole (11.3 g, 0.1 mol) and potassium carbonate (1.2 g) were added and the reaction mixture was refluxed for 6 hrs. The reaction mixture was cooled and poured into water (700 ml) and the yellow solid formed was filtered and dried. Yield 28.2 g) 89%). It was recrystallized from methanol. mp. 213°-214° C. 1H NMR (DMSO) ε 3.62 (m, 4H, PhthNCH2CHOH), 4.08 (m, 1H, CHOH), 4.32 and 4.63 (m, 2H, CHOHCH2N<), 5.54 (d, 1H, CHOH), 7.15 and 7.68 (s, 2H, imiH), 7.8 (m, 4H, ArH). MS: (M+H)+ =317+Anal. Calcd. for C14H12N4O5 : C, 53.17; H, 3.82; N, 17.71. Found C, 53.11; H, 3.76; N, 17.49.

Provenance & Evidence