Reaction #4208

Reaction equation

chloroacetyl chloride

potassium bicarbonate

3,4-dibenzyloxyaniline

chloroacetyl chloride

→

2-Chloro-N-[3,4-bis(phenylmethoxy)phenyl]acetamide

Solvents

acetonitrile water

Conditions

Workup

1. 1
   Temperaturewhile maintaining the pH at 6.5
2. 2
   workup.WAITWhen the pH remained constant for 15 minutes
3. 3
   Otherthe acetonitrile was evaporated
4. 4
   Filtrationthe resulting aqueous solution was filtered
5. 5
   WashThe precipitate was washed thoroughly with water
6. 6
   Otherto yield
7. 7
   Dryingupon drying in vacuo, 8.98 g of the title compound

Procedure

To 7.7 g (25 mmol) of 3,4-dibenzyloxyaniline in 50 ml of 1:1 acetonitrile/water at 0° C. was added chloroacetyl chloride (3.0 ml) while keeping the pH at 6.5 with saturated aqueous potassium bicarbonate. When the pH remained constant for 15 minutes, an additional 3 ml of chloroacetyl chloride was added in small portions while maintaining the pH at 6.5. When the pH remained constant for 15 minutes, the acetonitrile was evaporated, and the resulting aqueous solution was filtered. The precipitate was washed thoroughly with water to yield, upon drying in vacuo, 8.98 g of the title compound.

Source