Dimethylformamide → HCID 86657437, compound

Temperature

120 °C

Inside a glove box, a 250 mL round-bottom flask equipped with a stirring bar, reflux condenser, and a septum was charged with N-trifluoromethanesulfonyl-2,5-dibromo-benzene-sulfonamide, sodium salt (19.45 g, 50 mmoles), activated copper powder (40 g), and DMF (80 mL). The flask was heated to 120° C. under nitrogen and stirred overnight. The solution was cooled to room temperature, filtered, and the solids washed with DMF. The solvent was evaporated by distilling under high vacuum and the resulting solids were dried under vacuum. The dark solids were dissolved in water by heating to a reflux and adding hydrochloric acid to give pH of 1. Residual dark solids were filtered off then the solution was neutralized using aqueous sodium hydroxide, which gave a yellow-brown precipitate that was removed by filtration. The mixture was saturated with sodium chloride and concentrated at reflux to 400 mL. Upon cooling, magenta solids precipitated from solution. The solids were collected by vacuum filtration and dried under vacuum to give 13.2 g (68% crude yield). The solids were dissolved in methanol at a reflux, treated with decolorizing carbon, filtered, evaporated, and dried in a vacuum oven at 150° C. under nitrogen purge. The solids were recrystallized from dioxane (50 mL) inside the glove box after filtering off residual solids. The crystals were collected and washed with dioxane to remove much of the remaining magenta color. The recrystallization was repeated inside the glove box to give colorless crystals, which were dried in a vacuum oven at 150° C. under nitrogen purge and transferred to a glove box for storage and handling to give 10.78 g (55% yield) of N,N′-bis(trifluoromethanesulfonyl)-4,4′-dibromo-biphenyl-2,2′-disulfonamide, disodium salt. 19F NMR (DMSO-d6): −78.31 (s).

1. customInside a glove box, a 250 mL round-bottom flask equipped with a stirring bar
2. temperaturereflux condenser
3. temperatureThe solution was cooled to room temperature
4. filtrationfiltered
5. washthe solids washed with DMF
6. customThe solvent was evaporated
7. distillationby distilling under high vacuum
8. customthe resulting solids were dried under vacuum
9. dissolutionThe dark solids were dissolved in water
10. temperatureby heating to
11. temperaturea reflux
12. additionadding hydrochloric acid
13. customto give pH of 1
14. filtrationResidual dark solids were filtered off
15. customgave a yellow-brown precipitate that
16. customwas removed by filtration
17. concentrationconcentrated
18. temperatureat reflux to 400 mL
19. temperatureUpon cooling
20. custommagenta solids precipitated from solution
21. filtrationThe solids were collected by vacuum filtration
22. customdried under vacuum
23. customto give 13.2 g (68% crude yield)
24. additiontreated with decolorizing carbon
25. filtrationfiltered
26. customevaporated
27. customdried in a vacuum oven at 150° C. under nitrogen
28. custompurge
29. customThe solids were recrystallized from dioxane (50 mL) inside the glove box
30. filtrationafter filtering off residual solids
31. customThe crystals were collected
32. washwashed with dioxane
33. customto remove much of the remaining magenta color
34. customThe recrystallization
35. customto give colorless crystals, which
36. customwere dried in a vacuum oven at 150° C. under nitrogen
37. custompurge
38. customtransferred to a glove box for storage

ORD record

ord-aa851f64fecd405386bba47e1cb4714a

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08058383B2