Reacción #2159

Ecuación de reacción

4-Hydroxymethylimidazole hydrochloride

ρ-Toluenesulfonyl chloride

triethylamine

→

title compound

Rendimiento 80.0%

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

Rendimiento 80.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe mixture was washed with water (2×100 ml) and brine (1×100 ml)
2. 2
   Otrothe organic layer was dried
3. 3
   Otroevaporated
4. 4
   Otroto leave a clear oil which
5. 5
   Otrowas recrystallised from ethyl acetate/hexane

Procedimiento

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%).

Fuente