Sodium Hydroxide → HCID 68858921, compound

HRID 491275Notes

Reaction equation

HRID 491275 reaction equation
Cl[C:2]1C=CC=C(C(OO)=O)C=1.[F:12][CH:13]([F:24])[O:14][C:15]1[CH:16]=[C:17]([CH3:23])[C:18](SC)=[N:19][CH:20]=1.[OH-].[Na+].C(=O)(O)[O-].[Na+].[S:32]([O-:35])([O-])=[O:33].[Na+].[Na+]>C(Cl)Cl>[F:24][CH:13]([F:12])[O:14][C:15]1[CH:16]=[C:17]([CH3:23])[C:18]([S:32]([CH3:2])(=[O:35])=[O:33])=[N:19][CH:20]=1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 68857309HCID 68857309, compound

Product 1

HCID 68858921HCID 68858921, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid 3-chloroperbenzoic acid (60 percent, 18.1 g, 68.6 mmol) was added in portions over 1 hour to a chilled (6° C.) solution of 5-difluoromethoxy-3-methyl-2-methylsulfanylpyridine (6.4 g, 31.2 mmol) in methylene chloride (200 mL). The reaction was stirred overnight while warming to room temperature. Aqueous 1N sodium hydroxide (65 mL) was added in portions, raising the pH to ca. 6. Saturated aq. sodium bicarbonate (60 mL) was added, raising the pH of the aqueous phase to ca. 8. Aqueous 10 percent sodium sulfite was added, and after stirring for 10 minutes, the layers were separated. The aqueous layer was extracted with methylene chloride (50 mL) and the organic layers were combined, washed with brine, and dried (Na2SO4). Filtration and removal of solvent left a clear oil, 8 g, that was purified by chromatography on silica, eluting with 1.5 vol percent acetonitrile in methylene chloride to give product, 6.3 g, 26.6 mmol, 85 percent yield.

Workup

  1. temperatureraising the pH to ca. 6
  2. temperatureraising the pH of the aqueous phase to ca. 8
  3. stirringafter stirring for 10 minutes
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with methylene chloride (50 mL)
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationFiltration and removal of solvent
  9. waitleft a clear oil, 8 g, that
  10. customwas purified by chromatography on silica
  11. washeluting with 1.5 vol percent acetonitrile in methylene chloride
  12. customto give product, 6.3 g, 26.6 mmol, 85 percent yield

Sources & evidence

ORD record
ord-40eaea39712f4e8fbea50fb873544843
Source dataset
uspto-grants-2009_05
Patent number
US07531482B2

Reaction notes

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