Water → HCID 21097534, compound

HRID 1350850Notes

Reaction equation

HRID 1350850 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9](S(C)(=O)=O)[S:10]([CH3:13])(=[O:12])=[O:11])=[C:4]([F:18])[CH:3]=1.[OH-].[Na+].O>O1CCCC1>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH:9][S:10]([CH3:13])(=[O:11])=[O:12])=[C:4]([F:18])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 21097535HCID 21097535, compound

Product 1

HCID 21097534HCID 21097534, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(4-bromo-2,6-difluorophenyl)-N-(methylsulfonyl)methanesulfonamide (2.20 g, 6.04 mmol) and sodium hydroxide (pellet) (1.20 g, 30.0 mmol) in tetrahydrofuran. (30 ml) and water (10 ml) was stirred for 2 hours at ambient temperature. After the solvent was evaporated in vacuo and the residue was acidified to pH 2 with 2M hydrochloride aqueous solution. The aqueous solution was extracted with ethyl acetate and the combined solution was washed with brine, dried over sodium sulfate. After filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give a residue, which was recrystallized from ethyl acetate and hexane to furnish 1.55 g (90% yield) of the title compound as a white solid.

Workup

  1. customAfter the solvent was evaporated in vacuo
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. washthe combined solution was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. customto separate solvent and sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customto give a residue, which
  9. customwas recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-4ca5907fdd874b268a751e3ba2caf244
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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