Triethylamine → HCID 66993480, compound

HRID 557089Notes

Reaction equation

HRID 557089 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].[F:13][C:14]([F:20])([F:19])[S:15]([NH2:18])(=[O:17])=[O:16].C(N(CC)CC)C.[OH-].[Na+].[Na]>O.C(#N)C>[F:13][C:14]([F:20])([F:19])[S:15]([NH:18][S:9]([C:3]1[CH:4]=[C:5]([Br:8])[CH:6]=[CH:7][C:2]=1[Br:1])(=[O:11])=[O:10])(=[O:17])=[O:16]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 79001TrifluoromethylsulfonamideHCID 27375152,5-Dibromobenzenesulfonyl chlorideHCID 5360545Sodium

Product 1

HCID 66993480HCID 66993480, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Inside a glove box, a 200 mL round-bottom flask equipped with a reflux condenser, stirring bar, and septum was charged with 2,5-dibromo-benzene-sulfonyl chloride (16.72 g, 50 mmoles), trifluoromethanesulfonamide (7.45 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 dissolved in n-propanol at reflux, treated with decolorizing carbon, filtered to remove the carbon and residual salts, evaporated on a rotary evaporator, and dried under vacuum to give 23.54 g (100%). The solids were recrystallized from dioxane to give 12.77 g (54% 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. 1H NMR (DMSO-d6): 7.62 (dd, J=8 and 2 Hz, 1H), 7.69 (d, J=8 Hz, 1H), 8.05 (d, J=2 Hz, 1H).

Workup

  1. customInside a glove box, a 200 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. dissolutionThe solids were dissolved in n-propanol
  6. temperatureat reflux
  7. additiontreated with decolorizing carbon
  8. filtrationfiltered
  9. customto remove the carbon and residual salts
  10. customevaporated on a rotary evaporator
  11. customdried under vacuum
  12. customto give 23.54 g (100%)
  13. customThe solids were recrystallized from dioxane

Sources & evidence

ORD record
ord-9791389e730d4a9782f3027fe6792fcf
Source dataset
uspto-grants-2011_11
Patent number
US08058383B2

Reaction notes

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