Hydrogen Peroxide → HCID 23114637, compound

HRID 2080530Notes

Reaction equation

HRID 2080530 reaction equation
C(OCC)(=[O:3])C.[Cl:7][C:8]1[C:9]([CH:17]([S:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])=[CH:10][C:11]([CH2:14][C:15]#[N:16])=[N:12][CH:13]=1.CO.OO.[OH2:38]>CCCCCC>[Cl:7][C:8]1[C:9]([CH:17]([S:26]([C:27]2[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=2)(=[O:3])=[O:38])[C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])=[CH:10][C:11]([CH2:14][C:15]#[N:16])=[N:12][CH:13]=1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 962WaterHCID 8857Ethyl AcetateHCID 23114828HCID 23114828, compound

Product 1

HCID 23114637HCID 23114637, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To an ethyl acetate (5 ml) solution of [5-chloro-4-[(4-chlorophenylthio)(2,5-difluorophenyl)methyl]pyridin-2-yl]acetonitrile (387 mg, 0.92 mmol) were added methanol (5 ml), 31% aqueous hydrogen peroxide (3 ml) and hexaammonium heptamolybdate tetrahydrate (227 mg, 0.18 mmol). The resulting mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture. Ethyl acetate and methanol were distilled off under reduced pressure. To the residue was added a saturated aqueous solution of sodium bicarbonate. The product thus obtained was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=17:3 eluate was concentrated under reduced pressure to give the title compound (364 mg, 0.80 mmol, 87%) as a white solid.

Workup

  1. distillationEthyl acetate and methanol were distilled off under reduced pressure
  2. additionTo the residue was added a saturated aqueous solution of sodium bicarbonate
  3. customThe product thus obtained
  4. extractionwas extracted with dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe residue thus obtained
  9. concentrationethyl acetate=17:3 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a4a8762b4296421e9721f5d0a2124a8a
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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