Water → 2',4'-Difluoro-N-(3-(oxiran-2-yl)phenyl)biphenyl-4-sulfonamide

HRID 221391Notes

Reaction equation

HRID 221391 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]=[CH2:26])[CH:20]=2)(=[O:17])=[O:16])=[CH:11][CH:10]=1.[OH2:27]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[CH:11][C:12]([S:15]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]3[CH2:26][O:27]3)[CH:20]=2)(=[O:16])=[O:17])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 962WaterHCID 673295122',4'-Difluoro-N-(3-vinylphenyl)biphenyl-4-sulfonamide

Product 1

HCID 866562622',4'-Difluoro-N-(3-(oxiran-2-yl)phenyl)biphenyl-4-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dry meta-chloroperoxybenzoic acid (˜85%, dried over KOH in a clean, dry, uncontaminated vacuum desiccator for at least 48 hours; 3.7 g, 21 mmol) was added to a solution of 2′,4′-difluoro-N-(3-vinylphenyl)biphenyl-4-sulfonamide (1.16 g, 4.3 mmol) in dry DCM (30 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred for 5 hours. Water (30 mL) was added and the layers were separated. The DCM layer was washed with 10% Na2SO3 (30 mL), saturated NaHCO3 (30 mL), water (30 mL) and brine (30 mL) and dried over MgSO4. The solvent was evaporated and the title compound obtained as an orange oil (1.16 g) which was used without further purification.

Workup

  1. dry with materialDry meta-chloroperoxybenzoic acid (˜85%, dried over KOH in a clean,
  2. customdry
  3. waituncontaminated vacuum desiccator for at least 48 hours
  4. customthe layers were separated
  5. washThe DCM layer was washed with 10% Na2SO3 (30 mL), saturated NaHCO3 (30 mL), water (30 mL) and brine (30 mL)
  6. dry with materialdried over MgSO4
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b0b567b37f1345a59fe7ff70b1aa8a2b
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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