반응 #722072

반응 방정식

2-nitroimidazole

sodium bicarbonate

5-bromo-2-methyl-2-pentene

→

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

용매

water

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 dimethylformaide (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) δ 1.55 (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