Triethylamine → HCID 86621786, compound

Participants

Reaction Steps

Inside the glove box, a 200 mL round-bottom flask equipped with a reflux condenser, stirring bar, and septum was charged with 4′-bromo-biphenyl-4-sulfonyl chloride (8.36 g, 25.3 mmol), octafluorobutane-1,4-disulfonamide (4.550 g, 12.6 mmol), and acetonitrile (80 mL). Triethylamine (7.6 mL, 54.3 mmol) was added slowly by syringe to give a mild exotherm. The solution was heated to a reflux overnight. The solution was cooled to room temperature and poured into an aqueous solution of sodium hydroxide (4 g, 0.1 mol) in water (200 mL) in a 1 L round-bottom flask. The solvents were evaporated on a rotary evaporator and the solids were dried under vacuum. The solids were recrystallized by dissolving in water (300 mL) at a reflux, filtering the solution, and concentrating the solution at a reflux to induce crystallization. The white crystals were collected by vacuum filtration, washed with water, and dried overnight in a vacuum oven at 150° C. under a nitrogen purge to give 11.24 g (89% yield) of N,N′-bis(4′-bromo-biphenyl-4-sulfonyl)-octafluorobutane-1,4-disulfonamide, disodium salt.

Provenance & Evidence