반응 #75435

반응 방정식

5-bromo-2-methyl-2-pentene

2-nitroimidazole

sodium bicarbonate

→

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

용매

water

dimethylformamide

반응 조건

후처리

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

실험 절차

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.

출처