Reacción #75435

Ecuación de reacción

5-bromo-2-methyl-2-pentene

2-nitroimidazole

sodium bicarbonate

→

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

Disolventes

water

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroSolvent dimethylformamide and the unreacted bromide were removed under reduced pressure (<1 mm) at 50-60° C.
2. 2
   Otroto yield a paste which
3. 3
   Extracciónextracted with ethyl acetate (5×50 mL)
4. 4
   OtroThe combined organic extracts were dried
5. 5
   Concentraciónconcentrated
6. 6
   Otroto give a brown oil which
7. 7
   Otrowas recrystallized from petroleum ether (b.p. 40-60° C.)
8. 8
   Otroto yield a yellow solid

Procedimiento

To a solution of 2-nitroimidazole (3.0 g, 27 mmol) in dry dimethylformamide (25 mL), was added anhydrous sodium bicarbonate (4.2 g, 50 mmol) followed by 5-bromo-2-methyl-2-pentene (5.0 g, 30.67 mmol). The reaction mixture was heated at 60-70° C. with stirring under nitrogen for 16 hours. Solvent dimethylformamide and the unreacted bromide were removed under reduced pressure (<1 mm) at 50-60° C. to yield a paste which was dissolved in water (50 mL) and extracted with ethyl acetate (5×50 mL). The combined organic extracts were dried and concentrated to give a brown oil which was recrystallized from petroleum ether (b.p. 40-60° C.) to yield a yellow solid. Yield: 4.8 g, m.p. 51-52° C. 1H NMR (CDCl3) δ1.55 (s, 3H, CH3), 1.75 (s, 3H, CH3), 2.7 (q, 2H, olefinic CH2), 4.5 (t, 2H, N—CH2), 5.2 (t, 1H, olefinic H), 7.1 (s, 1H, imidazole H), 7.2 (s, 1H, imidazole H). M.S. [M+H]+ 196, [M+NH4]+ 213.

Fuente