Dichloromethane → HCID 23114889, compound

HRID 2080394Notes

Reaction equation

HRID 2080394 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 methylene chloride (15 ml) of the 3-[(4-chlorophenylsulfonyl)-(2,5-difluorophenyl)methyl]pyridine (162 mg, 0.427 mmol) obtained in Example 19 was added 3-chloroperbenzoic acid (81 mg, 0.47 mmol). The resulting mixture was stirred for 24 hours. The reaction mixture was diluted with ether (60 ml). The diluted mixture was washed with a saturated aqueous solution of sodium bicarbonate, water and brine, dried and filtered. The filtrate was concentrated under reduced pressure to give a residue. The resulting residue was subjected to silica gel chromatography (ethyl acetate) to give the title compound (68 mg, 40%). The compound was crystallized from ethanol to afford colorless needle crystals.

Workup

  1. washThe diluted mixture was washed with a saturated aqueous solution of sodium bicarbonate, water and brine
  2. customdried
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give a residue

Sources & evidence

ORD record
ord-29d25421f4304d9ea485023b15bba9c2
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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