Reaction #65205

Reaction equation

HCl

5-(2-chlorobenzoylamino)indan

2-chlorobenzoyl chloride

tin tetrachloride

→

6-(2-chlorobenzoyl)-5-(2-chlorobenzoylamino)indan

Yield 66.2%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   OtherThe organic layer was separated
2. 2
   Washwashed with water, 2N NaOH and water in the order
3. 3
   workup.DISTILLATIONthe solvent was distilled off
4. 4
   OtherThe residue was chromatographed on silica gel
5. 5
   Washeluted with hexane-acetone (4:1)

Procedure

A mixture of 5-(2-chlorobenzoylamino)indan (16 g), 2-chlorobenzoyl chloride (15.5 g) and tin tetrachloride (10.2 ml) was heated at 130° C. for 30 minutes and, then, diluted with ethyl acetate (150 ml), followed by addition of 3N HCl (150 ml). The organic layer was separated and washed with water, 2N NaOH and water in the order mentioned and the solvent was distilled off. The residue was chromatographed on silica gel and eluted with hexane-acetone (4:1) to give 6-(2-chlorobenzoyl)-5-(2-chlorobenzoylamino)indan as oil (16.0 g, 66.2%).

Source