Dichloromethane → HCID 23114889, compound

HRID 748836Notes

Reaction equation

HRID 748836 reaction equation
C(Cl)Cl.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[F:28])[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1.ClC1C=CC=C(C(OO)=[O:37])C=1.C(OCC)(=O)C>CCOCC>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[F:28])[C:15]2[CH:16]=[N+:17]([O-:37])[CH:18]=[CH:19][CH:20]=2)(=[O:12])=[O:13])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 231146123-[(4-Chlorobenzene-1-sulfonyl)(2,5-difluorophenyl)methyl]pyridine

Product 1

HCID 23114889HCID 23114889, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a methylene chloride solution (15 ml) of the 3-[(4-chlorophenylsulfonyl)-(2,5-difluorophenyl)methyl]pyridine (162 mg, 0.427 mmol) obtained in Example 141 was added 3-chloroperbenzoic acid (81 mg, 0.47 mmol) and the mixture was stirred for 24 hours. The reaction mixture was diluted with ether (60 ml), followed by washing with a saturated aqueous solution of sodium bicarbonate, water and brine. After drying, the solution was filtered and the filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel chromatography (ethyl acetate), whereby the title compound (68 mg, 40%) was obtained. The compound was crystallized from ethanol and was obtained as colorless needle crystals.

Workup

  1. washby washing with a saturated aqueous solution of sodium bicarbonate, water and brine
  2. customAfter drying
  3. filtrationthe solution was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue thus obtained

Sources & evidence

ORD record
ord-2331d13ca27840cda4f9102e79b463be
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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