Triethylamine → HCID 86657438, compound

Participants

Reaction Steps

Inside a glove box, a 250 mL round-bottom flask equipped with a stirring bar, reflux condenser, and a septum was charged with 4,4′-dibromo-biphenyl-3,3′-disulfonyl dichloride (10.95 g, 21.5 mmoles), trifluoromethanesulfonamide (6.41 g, 43 mmoles), and acetonitrile (75 mL). Triethylamine (13 mL, 93 mmoles) was added slowly by syringe. The solution was heated to a reflux and stirred overnight under nitrogen. The solution was cooled to room temperature and poured into an aqueous solution of sodium hydroxide (3.5 g, 88 mmoles) in 400 mL water. The solvents were evaporated on a rotary evaporator and the solids were dried under vacuum. The solids were dissolved in n-propanol at reflux, filtered to remove insolubles and salt, treated with decolorizing carbon, filtered to remove the carbon, evaporated on a rotary evaporator, and dried under vacuum to give 16.8 g (100%). The solids were recrystallized from n-propanol using decolorizing carbon again and collecting three crops for a combined weight of 13.75 g (82% yield). The solids were recrystallized from n-propanol as needles in two crops by allowing for slow evaporation of the solvent. The crystals were dried under vacuum to give a total of 9.61 g (57%) of N,N′-bis(trifluoromethanesulfonyl)-4,4′-dibromo-biphenyl-3,3′-disulfonamide, disodium salt. 1H NMR (DMSO-d6): 7.69 (dd, J=8.2 and 2.4 Hz, 2H), 7.87 (d, J=8.2 Hz, 2H), 8.03 (d, J=2.4 Hz, 2H). 19F NMR (DMSO-d6): −78.2 (s). The compound was redried at 150° C. overnight in a nitrogen-purged vacuum oven then transferred immediately to the glove box.

Provenance & Evidence