Reaction #8647

Reaction equation

1-(4-nitrophenyl)[1,4]diazepane

potassium carbonate

chloroacetyl chloride

→

yellow crystals

Yield 75.2%

2-chloro-1-[4-(4-nitrophenyl)[1,4]diazepan-1-yl]ethanone

Yield 75.2%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   Temperaturewhile maintaining the temperature between 15 and 25° C
2. 2
   workup.ADDITION400 g of slightly hydrochloric ice-cold water were added to the mixture
3. 3
   Othera yellow gum crystallized
4. 4
   FiltrationAfter filtering off by suction
5. 5
   Washwashing with water
6. 6
   Dryingdrying under vacuum over phosphorus pentoxide

Procedure

22.1 g (0.1 mol) of 1-(4-nitrophenyl)[1,4]diazepane, 8.3 g (0.06 mol) of potassium carbonate and 120 ml of dimethylformamide were mixed together in a reactor. 8.3 ml (0.11 mol) of chloroacetyl chloride were added to this stirred suspension, while maintaining the temperature between 15 and 25° C. After stirring for about ten hours at room temperature, 400 g of slightly hydrochloric ice-cold water were added to the mixture: a yellow gum crystallized. After filtering off by suction, washing with water and drying under vacuum over phosphorus pentoxide, 22.4 g of yellow crystals were obtained (yield=75%).

Source