m-Chloroperbenzoic acid → HCID 57736503, compound

HRID 1641692Notes

Reaction equation

HRID 1641692 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[C:10]1[C:11]([CH3:19])=[CH:12][C:13]([C:16]([NH2:18])=[O:17])=[N:14][CH:15]=1.ClC1C=CC=C(C(OO)=[O:36])C=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:20]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=[O:36])[C:10]1[C:11]([CH3:19])=[CH:12][C:13]([C:16]([NH2:18])=[O:17])=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57736528HCID 57736528, compound

Product 1

HCID 57736503HCID 57736503, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[(2,5-difluorophenyl) [(4-fluorophenyl)thio]methyl]-4-meth ylpyridine-2-carboxamide (152 mg, 0.39 mmol) in methylene chloride (5 ml), 3-chloroperbenzoic acid (104 mg, 0.39 mmol) was added at 0° C. After stirring for 2 hours at room temperature, the reaction mixture was washed with 1 N aqueous sodium hydroxide. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to flash silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=7:3 was concentrated under reduced pressure, and the resulting residue was washed with a mixed solvent of ethanol and hexane, and was collected by filtration to obtain the title compound (91 mg, 0.23 mmol, 58%) as a white solid.

Workup

  1. washthe reaction mixture was washed with 1 N aqueous sodium hydroxide
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe fraction obtained from an elution with hexane
  6. concentrationethyl acetate=7:3 was concentrated under reduced pressure
  7. washthe resulting residue was washed with a mixed solvent of ethanol and hexane
  8. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-1893e4b2d2f847d7bdaafa0a7dae61ed
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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