Reaktion #58972

Reaktionsgleichung

4-methyl-1H-imidazole

4-nitrobenzyl bromide

potassium carbonate

N,N-dimethylformamide

→

5-methyl-1-(4-nitrobenzyl)-1H-imidazole

Ausbeute 3.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with ethyl acetate
2. 2
   WaschenThe organic layer was washed with water
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Einengenconcentrated

Vorschrift

A mixture of 4-methyl-1H-imidazole (25.5 g), 4-nitrobenzyl bromide (56 g), potassium carbonate (86 g) and N,N-dimethylformamide (500 ml) was stirred at room temperature for 14 hrs. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to give 5-methyl-1-(4-nitrobenzyl)-1H-imidazole (1.6 g, 3%) as crystals from a fraction eluted with methanol-ethyl acetate (1:20, v/v). Recrystallization thereof from ethyl acetate-isopropyl ether gave colorless prism crystals. melting point: 120-121° C.

Quelle