1,2-Dibromoethane → N-(2-bromoethyl)-N-(4-nitrophenyl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

1,2-Dibromoethane (2.26 kg, 12 mol) mixed with 4 L of dimethylformamide was brought to 80° C. 1.264 kg (4 mol) of the potassium salt of N-(4-nitrophenyl)benzenesulfonamide (5) was added in portions and the mixture was stirred at 90-95° C. for 4 hours. The resulting mixture was filtered while hot and a KBr salt was formed, which was washed with dimethylformamide. The filtrate was poured onto 20 kg of ice in 20 kg of water. A yellow precipitate formed, which was filtered off by suction, reslurried three times in hot 1N sodium hydroxide, and then reslurried in water to neutral pH. The crude product (1.2 kg wet) obtained was recrystallized from 3 L of acetic acid. This mixture was filtered while boiling and the filtrate was cooled to 20° C. A white precipitate formed, which was filtered off by suction, washed with acetic acid and then with petroleum ether, and then dried under vacuum. 773 g product with a melting temperature of 168° C. were isolated.

Provenance & Evidence