Triethylamine → HCID 66993480, compound

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.

1. customInside a glove box, a 100 mL round-bottom flask equipped with a reflux condenser
2. temperatureThe solution was heated to a reflux overnight
3. customThe solvents were evaporated on a rotary evaporator
4. customthe solids were dried under vacuum
5. customThe solids were recrystallized
6. dissolutionby dissolving in dioxane at a reflux
7. additiontreating with decolorizing carbon
8. filtrationfiltering the solution
9. concentrationconcentrating the solution at
10. temperaturea reflux to 130 mL
11. customcrystallization
12. filtrationThe white crystals were collected by vacuum filtration
13. washwashed with dioxane
14. customdried under vacuum
15. customThe recrystallization

ORD record

ord-d9f0672a2d114f118479801d8031beab

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08058383B2