반응 #2159

반응 방정식

4-Hydroxymethylimidazole hydrochloride

ρ-Toluenesulfonyl chloride

triethylamine

→

title compound

수율 80.0%

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

수율 80.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   세척The mixture was washed with water (2×100 ml) and brine (1×100 ml)
2. 2
   기타the organic layer was dried
3. 3
   기타evaporated
4. 4
   기타to leave a clear oil which
5. 5
   기타was recrystallised from ethyl acetate/hexane

실험 절차

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%).

출처