Reaction #4527

Reaction equation

chloroethyl chloroformate

imidazole

dichloromethane

water

→

α-chloroethoxycarbonylimidazole

Conditions

Workup

1. 1
   Temperaturecooled in a water bath
2. 2
   WashThe organic phase is washed with 2×50 ml of water
3. 3
   Dryingdried over magnesium sulphate
4. 4
   OtherAfter evaporation and distillation, 38.1 g (73%) of α-chloroethoxycarbonylimidazole [B.p. 80° C./66.6 Pa (0.5 mm Hg)]
5. 5
   Otherare obtained in the form of a colourless liquid which
6. 6
   Othercrystallises spontaneously at room temperature

Procedure

28.6 g (0.2 mole) of chloroethyl chloroformate are added dropwise to a solution of 27.2 g (0.4 mole) of imidazole in 200 ml of dichloromethane cooled in a water bath. The mixture is stirred at room temperature for 4 hours, and 50 ml of iced water are then added. The organic phase is washed with 2×50 ml of water and then dried over magnesium sulphate. After evaporation and distillation, 38.1 g (73%) of α-chloroethoxycarbonylimidazole [B.p. 80° C./66.6 Pa (0.5 mm Hg)] are obtained in the form of a colourless liquid which crystallises spontaneously at room temperature, m.p. 50° C. ##STR57##

Source