Reaction #2275

Reaction equation

ethyl acetate

4-chloroaniline

pyridine

cinnamoyl chloride

→

amide

N-(4-chlorophenyl)cinnamamide

Solvents

toluene

toluene

water

Conditions

Workup

1. 1
   OtherThe organic layer was separated
2. 2
   Extractionextracted with 5% aqueous HCl (3×250 ml), water (1×250 ml), 5% aqueous sodium bicarbonate (3×250 ml)
3. 3
   Dryingdried over anhydrous sodium sulfate
4. 4
   Otherevaporated

Procedure

To a mixture of 4-chloroaniline (16.2 g), toluene (120 ml), and pyridine (11 ml) at 0° C., cinnamoyl chloride (20.0 g) in 120 ml of toluene was added dropwise. After stirring 15 minutes at 0° C. the reaction mixture was poured into a mixture of ethyl acetate: water (250 ml:250 ml). The organic layer was separated and extracted with 5% aqueous HCl (3×250 ml), water (1×250 ml), 5% aqueous sodium bicarbonate (3×250 ml), dried over anhydrous sodium sulfate and evaporated yielding the amide as a white solid.

Source