Reaktion #2159

Reaktionsgleichung

4-Hydroxymethylimidazole hydrochloride

ρ-Toluenesulfonyl chloride

triethylamine

→

title compound

Ausbeute 80.0%

4-Hydroxymethyl-N-(ρ-toluenesulfonyl)imidazole

Ausbeute 80.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe mixture was washed with water (2×100 ml) and brine (1×100 ml)
2. 2
   Sonstigethe organic layer was dried
3. 3
   Sonstigeevaporated
4. 4
   Sonstigeto leave a clear oil which
5. 5
   Sonstigewas recrystallised from ethyl acetate/hexane

Vorschrift

4-Hydroxymethylimidazole hydrochloride (10 g) was suspended in dichloromethane (200 ml). ρ-Toluenesulfonyl chloride (15.58 g) was added and triethylamine (25.8 ml) was added dropwise to the stirred reaction mixture which was allowed to stir at room temperature overnight. The mixture was washed with water (2×100 ml) and brine (1×100 ml) and the organic layer was dried and evaporated to leave a clear oil which was recrystallised from ethyl acetate/hexane to afford the title compound as a white crystalline solid (15 g, 80%). 1H NMR (360 MHz, CDCl3) δ2.44 (3H, s), 4.55 (2H, s), 7.21 (1H, s), 7.35 (2H, d, J=8.0 Hz), 7.62 (2H, d, J=8.0 Hz 7.98 (1H, s). MS (CI+) m/z 253 (M+H, 100%).

Quelle