Reaktion #75435

Reaktionsgleichung

5-bromo-2-methyl-2-pentene

2-nitroimidazole

sodium bicarbonate

→

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

Lösungsmittel

water

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle