m-Chloroperbenzoic acid → HCID 67548323, compound

HRID 2356716Notes

Reaction equation

HRID 2356716 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:9][C:10]([CH2:19][S:20][CH3:21])=[C:11]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[N:12]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:22]C1C=CC=C(C(OO)=[O:30])C=1.C(=O)([O-])O.[Na+]>O1CCCC1>[ClH:22].[F:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:9][C:10]([CH2:19][S:20]([CH3:21])=[O:30])=[C:11]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 67547429HCID 67547429, compound

Product 1

HCID 67548323HCID 67548323, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-fluorophenyl)-5-methylthiomethyl-4-(3-pyridyl)imidazole (152 mg) in tetrahydrofuran (10 ml) was added metachloroperbenzoic acid (97 mg, 70% purity) under ice-cooling, and the mixture was stirred at room temperature for 5 hours. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: chloroform:methanol=19:1), and then, treated with hydrogen chloride-dioxane solution to obtain 2-(3-fluorophenyl)-5-methylsulfinylmethyl-4-(3-pyridyl)imidazole hydrochloride (140 mg) as colorless powder.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (solvent: chloroform:methanol=19:1)
  7. additiontreated with hydrogen chloride-dioxane solution

Sources & evidence

ORD record
ord-ecfae68169a3417a8540c78c127a886d
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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