Benzenesulfonamide, 4-(bromomethyl)-N-cyclopropyl- synthesis

Yield:-

Reaction Conditions:

with triethylamine in dichloromethane at -10; for 1 h;Inert atmosphere;

Steps:

Preparation of 4-(bromomethyl)-N-cyclopropylbenzenesulfonamide

5 g of 4-(bromomethyl)benzenesulfonyl chloride (18.6 mmol, 1 eq.) were dissolved under argon atmosphere in 82,5 ml of dichloromethane and cooled down at -10? internal temperature. A solution of 1.29 ml cyclopropanamine (18.6 mmol, 1 eq.) and 2.59 ml of triethylamine (18.6 mmol, 1 eq.) in 82,5 ml of dichloromethane were added dropwise at - 10? internal temperature and stirred at this temperature for one hour. The reaction mixture was washed once with 1 M aqueous hy- drogene solution and twice with distilled water. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude product contained a mixture of bromomethyl- and chloromethyl- substituents.

References:

WO2013/50438,2013,A1 Location in patent:Page/Page column 151