Triethylamine → HCID 86621786, compound

HRID 252432Notes

Reaction equation

HRID 252432 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[F:18][C:19]([F:37])([S:33]([NH2:36])(=[O:35])=[O:34])[C:20]([F:32])([F:31])[C:21]([F:30])([F:29])[C:22]([F:28])([F:27])[S:23]([NH2:26])(=[O:25])=[O:24].C(N([CH2:43][CH3:44])CC)C.[OH-:45].[Na+].[Na][Na]>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:36][S:33]([C:19]([F:18])([F:37])[C:20]([F:32])([F:31])[C:21]([F:29])([F:30])[C:22]([F:27])([F:28])[S:23]([NH:26][S:14]([C:11]3[CH:12]=[CH:13][C:8]([C:44]4[CH:43]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=4)=[CH:9][CH:10]=3)(=[O:15])=[O:45])(=[O:24])=[O:25])(=[O:35])=[O:34])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 141233DisodiumHCID 27568454'-Bromobiphenyl-4-sulfonyl chlorideHCID 11631855octafluorobutane-1,4-disulfonamide

Product 1

HCID 86621786HCID 86621786, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Inside the glove box, a 100 mL round-bottom flask equipped with a reflux condenser, stirring bar, and septum was charged with 4′-bromo-biphenyl-4-sulfonyl chloride (6.63 g, 20 mmol), octafluorobutane-1,4-disulfonamide (3.60 g, 10 mmol), and acetonitrile (40 mL). Triethylamine (6 mL, 40 mmol) was added slowly by syringe. The solution was heated to a reflux overnight. The solution was cooled to room temperature, poured into an aqueous solution (150 mL) of 20% sodium hydroxide, and chilled in an ice bath to induce precipitation. The precipitate was collected by vacuum filtration dried under vacuum to give 9.86 g (99% yield). The solids were recrystallized by dissolving in water at a reflux, treating with decolorizing carbon, filtering the solution, and concentrating the solution at a reflux to 200 mL to induce crystallization. The white crystals were collected by vacuum filtration, washed with water, and dried overnight in a vacuum oven at 100° C. followed by 170° C. under a nitrogen purge to give 8.80 g (89% yield) of N,N′-bis(4′-bromo-biphenyl-4-sulfonyl)-octafluorobutane-1,4-disulfonamide, disodium salt, shown below. 1H NMR (DMSO-d6): 7.67 (bm, 4H), 7.78 (d, J=8 Hz, 2H), 7.84 (d, J=8 Hz, 2H). 19F NMR (DMSO-d6): −120.36 (m, —CF2—CF2—), −113.06 (m, 2 —CF2—SO2—).

Workup

  1. customInside the glove box, a 100 mL round-bottom flask equipped with a reflux condenser
  2. temperatureThe solution was heated to a reflux overnight
  3. temperaturechilled in an ice bath
  4. customprecipitation
  5. filtrationThe precipitate was collected by vacuum filtration
  6. customdried under vacuum
  7. customto give 9.86 g (99% yield)
  8. customThe solids were recrystallized
  9. dissolutionby dissolving in water at a reflux
  10. additiontreating with decolorizing carbon
  11. filtrationfiltering the solution
  12. concentrationconcentrating the solution at
  13. temperaturea reflux to 200 mL
  14. customcrystallization
  15. filtrationThe white crystals were collected by vacuum filtration
  16. washwashed with water
  17. customdried overnight in a vacuum oven at 100° C.
  18. customfollowed by 170° C. under a nitrogen
  19. custompurge

Sources & evidence

ORD record
ord-b7e37874d6ee4593a740e8b040d06d23
Source dataset
uspto-grants-2011_01
Patent number
US07868086B2

Reaction notes

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