Triethylamine → HCID 66993480, compound

Participants

Reaction Steps

Inside a glove box, a 100 mL round-bottom flask equipped with a reflux condenser, stirring bar, and septum was charged with 2,5-dibromo-benzene-sulfonyl chloride (16.35 g, 50 mmoles), trifluoromethanesulfonamide (7.27 g, 50 mmoles), and acetonitrile (50 mL). Triethylamine (14 mL, 100 mmoles) was added slowly by syringe. The solution was heated to a reflux overnight. The solution was cooled to room temperature and poured into an aqueous solution of sodium hydroxide (4.0 g, 100 mmoles) in 100 mL water. The solvents were evaporated on a rotary evaporator and the solids were dried under vacuum. The solids were recrystallized by dissolving in dioxane at a reflux, treating with decolorizing carbon, filtering the solution, and concentrating the solution at a reflux to 130 mL to induce crystallization. The white crystals were collected by vacuum filtration, washed with dioxane, and dried under vacuum. The recrystallization was repeated to give 19.45 g (83% yield) of N-trifluoromethanesulfonyl-2,5-dibromo-benzene-sulfonamide, sodium salt. The salt was dried overnight in a vacuum oven at 150° C. under a nitrogen purge.

Provenance & Evidence