Reaction #2159

Reaction equation

4-Hydroxymethylimidazole hydrochloride

ρ-Toluenesulfonyl chloride

triethylamine

→

title compound

Yield 80.0%

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

Yield 80.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   WashThe mixture was washed with water (2×100 ml) and brine (1×100 ml)
2. 2
   Otherthe organic layer was dried
3. 3
   Otherevaporated
4. 4
   Otherto leave a clear oil which
5. 5
   Otherwas recrystallised from ethyl acetate/hexane

Procedure

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%).

Source