Chlorosuccinimide → 2-Chloro-4-dodecylsulfonylaniline

Participants

Reaction Steps

A mixture of 4-dodecylsulphonylaniline (519.8 g, 1.6 moles), 1,2-dichlorethane (2.5 liters) and N-chlorosuccinimide (NCS) (110 g, 0.825 moles) was stirred at reflux for 45 minutes, then a further 60 g (0.45 moles) of NCS added. Refluxing was continued for another 45 minutes and another 53 g of NCS was added. The mixture was refluxed for another hour. The total amount of NCS used was 223 g (1.67 moles). TLC showed no starting material. The solvent was removed on the rotavapor, the residue dissolved in ethyl acetate (2 liters), washed with 3×1.5 liters of hot water, dried (MgSO4) and the solvent removed. The product was recrystallized twice from petroleum ether plus a little ethyl acetate to give 513.6 g (89%).

Provenance & Evidence