Hydrogen Peroxide → HCID 23114649, compound

HRID 2080512Notes

Reaction equation

HRID 2080512 reaction equation
[CH3:1][OH:2].[Cl:3][C:4]1[C:5]([CH:12]([S:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[CH:6][C:7](CO)=[N:8][CH:9]=1.OO.[OH2:31].C(OCC)(=[O:34])C>CCCCCC>[Cl:3][C:4]1[C:5]([CH:12]([S:21]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)(=[O:34])=[O:31])[C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[CH:6][C:7]([CH2:1][OH:2])=[N:8][CH:9]=1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 962WaterHCID 8857Ethyl AcetateHCID 23114767HCID 23114767, compound

Product 1

HCID 23114649HCID 23114649, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a methanol (5 ml) solution of [5-chloro-4-[(4-chlorophenylthio)(2,5-difluorophenyl)methyl]pyridin-2-yl]methanol (130 mg, 0.315 mmol) were added hexaammonium heptamolybdate tetrahydrate (20 mg) and 30% aqueous hydrogen peroxide (3 ml). The resulting mixture was stirred for 6 hours. After water was added to the reaction mixture, the resulting mixture was extracted with ethyl acetate. The extract was washed sequentially with water, a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium thiosulfate and brine. The organic layer thus obtained was dried over magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=2:1 eluate was concentrated under reduced pressure. The residue was recrystallized from hexane:ethyl acetate to give the title compound (101 mg, 0.227 mmol, 72%) as a white powder.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed sequentially with water
  3. customThe organic layer thus obtained
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue thus obtained
  7. concentrationethyl acetate=2:1 eluate was concentrated under reduced pressure
  8. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-a919af28d0aa41d4a0243081683bba0f
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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