Triethylamine → HCID 86621786, compound

HRID 252433Notes

Reaction equation

HRID 252433 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]>O.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

8

Reactant 5

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

Product 1

HCID 86621786HCID 86621786, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Inside the glove box, a 200 mL round-bottom flask equipped with a reflux condenser, stirring bar, and septum was charged with 4′-bromo-biphenyl-4-sulfonyl chloride (8.36 g, 25.3 mmol), octafluorobutane-1,4-disulfonamide (4.550 g, 12.6 mmol), and acetonitrile (80 mL). Triethylamine (7.6 mL, 54.3 mmol) was added slowly by syringe to give a mild exotherm. 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 g, 0.1 mol) in water (200 mL) in a 1 L round-bottom flask. The solvents were evaporated on a rotary evaporator and the solids were dried under vacuum. The solids were recrystallized by dissolving in water (300 mL) at a reflux, filtering the solution, and concentrating the solution at a reflux to induce crystallization. The white crystals were collected by vacuum filtration, washed with water, and dried overnight in a vacuum oven at 150° C. under a nitrogen purge to give 11.24 g (89% yield) of N,N′-bis(4′-bromo-biphenyl-4-sulfonyl)-octafluorobutane-1,4-disulfonamide, disodium salt.

Workup

  1. customInside the glove box, a 200 mL round-bottom flask equipped with a reflux condenser
  2. customto give a mild exotherm
  3. temperatureThe solution was heated to a reflux overnight
  4. customThe solvents were evaporated on a rotary evaporator
  5. customthe solids were dried under vacuum
  6. customThe solids were recrystallized
  7. dissolutionby dissolving in water (300 mL) at a reflux
  8. filtrationfiltering the solution
  9. concentrationconcentrating the solution at
  10. temperaturea reflux
  11. customcrystallization
  12. filtrationThe white crystals were collected by vacuum filtration
  13. washwashed with water
  14. customdried overnight in a vacuum oven at 150° C. under a nitrogen
  15. custompurge

Sources & evidence

ORD record
ord-a6f4072069f34518a315f8c105d60447
Source dataset
uspto-grants-2011_01
Patent number
US07868086B2

Reaction notes

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