Réaction #75435

Équation de réaction

5-bromo-2-methyl-2-pentene

2-nitroimidazole

sodium bicarbonate

→

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

Solvants

water

dimethylformamide

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source