Reaction #1509636

Reaction equation

triethylamine

4-bromo-benzoyl chloride

N-phenylbenzene-1,2-diamine

→

Compound 8

4-Bromo-N-(2-(phenylamino)phenyl)benzamide

Solvents

dichloromethane

Conditions

Workup

1. 1
   FiltrationSubsequent filtration

Procedure

To a solution of 4-bromo-benzoyl chloride (11 g, 50 mmol) in anhydrous dichloromethane (DCM) (100 ml), was added N-phenylbenzene-1,2-diamine (10.2 g, 55 mmol), then triethylamine (17 ml, 122 mmol) slowly. The whole mixture was then stirred at room temperature (r.t.) overnight. Subsequent filtration gave a white solid (Compound 8) (6.5 g). The filtrate was worked up with water (300 ml), and then extracted with DCM (300 ml) three times. The resulting organic phase was collected and dried over MgSO4, concentrated and recrystallized in DCM/hexanes to give another portion of white solid (Compound 8) (10.6 g). The total amount of product (Compound 8) was 17.1 g, in 93% yield.

Source