反応 #75435

反応方程式

5-bromo-2-methyl-2-pentene

2-nitroimidazole

sodium bicarbonate

→

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

溶媒

water

dimethylformamide

反応条件

後処理

1. 1
   その他Solvent dimethylformamide and the unreacted bromide were removed under reduced pressure (<1 mm) at 50-60° C.
2. 2
   その他to yield a paste which
3. 3
   抽出extracted with ethyl acetate (5×50 mL)
4. 4
   その他The combined organic extracts were dried
5. 5
   濃縮concentrated
6. 6
   その他to give a brown oil which
7. 7
   その他was recrystallized from petroleum ether (b.p. 40-60° C.)
8. 8
   その他to yield a yellow solid

実験手順

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.

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