Dichloromethane → HCID 23114554, compound

HRID 748837Notes

Reaction equation

HRID 748837 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:20]=[CH:19][N:18]=[CH:17][CH:16]=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:6]=[CH:7][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]=[CH:17][N+:18]([O-:37])=[CH:19][CH:20]=2)(=[O:12])=[O:13])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 231146584-[(4-Chlorobenzene-1-sulfonyl)(2,5-difluorophenyl)methyl]pyridine

Product 1

HCID 23114554HCID 23114554, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a methylene chloride solution (20 ml) of the 4-[(4-chlorophenylsulfonyl)-(2,5-difluorophenyl)methyl]pyridine (221 mg, 0.58 mmol) obtained in Example 142 was added 3-chloroperbenzoic acid (100 mg, 0.58 mmol) and the mixture was stirred for 20 hours. The reaction mixture was diluted with ether (60 ml), followed by washing with a saturated aqueous solution of sodium bicarbonate, water and brine. The solution was dried and then filtered. The filtrate was then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel chromatography (ethyl acetate) to yield the title compound (183 mg, 80%). The compound was then crystallized from ethanol and obtained as colorless needle crystals.

Workup

  1. washby washing with a saturated aqueous solution of sodium bicarbonate, water and brine
  2. customThe solution was dried
  3. filtrationfiltered
  4. concentrationThe filtrate was then concentrated under reduced pressure
  5. customThe residue thus obtained

Sources & evidence

ORD record
ord-c1cd28a387454d60b3fbd7956f4f59b5
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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