Reaction #75434

Reaction equation

Sodium bicarbonate

dimethylallyl bromide

2-nitroimidazole

→

N-(Dimethylallyl)-2-nitroimidazole

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperatureunder reflux for 16 hours
2. 2
   OtherThe solvent was removed under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
4. 4
   FiltrationThe solution was filtered
5. 5
   Dryingdried with anhydrous sodium sulfate
6. 6
   OtherRemoval of the solvent
7. 7
   Othergave an oil which
8. 8
   Otherwas recrystallized from petroleum ether (35-50° C.)

Procedure

Sodium bicarbonate (0.42 g, 50 mmol) and dimethylallyl bromide (3.28 g, 22 mmol) were added to a suspension of 2-nitroimidazole (2.26 g, 20 mmol) in dry acetonitrile (10 mL). The mixture was stirred under reflux for 16 hours. The solvent was removed under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was filtered, and dried with anhydrous sodium sulfate. Removal of the solvent gave an oil which was recrystallized from petroleum ether (35-50° C.). Yield 1.83 g, m.p. 48-49° C. 1H NMR (CDCl3) δ7.24 (s, 1H), 7.22 (s, 1H), 5.46 (m, 1H), 5.1 (d, 2H), 1.91 (s, 3H) and 1.90 (s, 3H).

Source