Triethylamine → HCID 86657438, compound

HRID 557093Notes

Reaction equation

HRID 557093 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[C:10]([S:15](Cl)(=[O:17])=[O:16])[CH:9]=2)=[CH:4][C:3]=1[S:19](Cl)(=[O:21])=[O:20].[F:23][C:24]([F:30])([F:29])[S:25]([NH2:28])(=[O:27])=[O:26].C(N(CC)CC)C.[OH-:38].[Na+]>O.C(#N)C>[F:23][C:24]([F:30])([F:29])[S:25]([NH:28][S:19]([C:3]1[CH:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[C:10]([S:15]([NH:28][S:25]([C:24]([F:30])([F:29])[F:23])(=[O:26])=[O:38])(=[O:17])=[O:16])[CH:9]=2)[CH:6]=[CH:7][C:2]=1[Br:1])(=[O:21])=[O:20])(=[O:27])=[O:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 79001TrifluoromethylsulfonamideHCID 20466968HCID 20466968, compound

Product 1

HCID 86657438HCID 86657438, compoundYield 60.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  1. customInside a glove box, a 250 mL round-bottom flask equipped with a stirring bar
  2. temperaturereflux condenser
  3. temperatureThe solution was heated to
  4. temperaturea reflux
  5. customThe solvents were evaporated on a rotary evaporator
  6. customthe solids were dried under vacuum
  7. dissolutionThe solids were dissolved in n-propanol
  8. temperatureat reflux
  9. filtrationfiltered
  10. customto remove insolubles and salt
  11. additiontreated with decolorizing carbon
  12. filtrationfiltered
  13. customto remove the carbon
  14. customevaporated on a rotary evaporator
  15. customdried under vacuum
  16. customto give 16.8 g (100%)
  17. customThe solids were recrystallized from n-propanol using
  18. customcollecting three crops for a combined weight of 13.75 g (82% yield)
  19. customThe solids were recrystallized from n-propanol as needles in two crops
  20. customby allowing for slow evaporation of the solvent
  21. customThe crystals were dried under vacuum

Sources & evidence

ORD record
ord-a37d605344dd4674842cf0495b6d1693
Source dataset
uspto-grants-2011_11
Patent number
US08058383B2

Reaction notes

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