Hydrogen Peroxide → HCID 21099505, compound

HRID 2376964Notes

Reaction equation

HRID 2376964 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1.C(=O)([O-])[O-:29].[K+].[K+].OO.[Na]>CS(C)=O.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:12]=[CH:13][C:14]([S:17]([C:20]2[CH:27]=[CH:26][C:23]([C:24]([NH2:25])=[O:29])=[CH:22][CH:21]=2)(=[O:18])=[O:19])=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 5360545SodiumHCID 21099507HCID 21099507, compound

Product 1

HCID 21099505HCID 21099505, compoundYield 182.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 4-({4-[(E)-2-(2,4-difluorophenyl)vinyl]phenyl}sulfonyl)benzonitrile (Example 53, 50 mg, 0.13 mmol) in dimethylsulfoxide (1.3 mL) was added potassium carbonate (9 mg, 0.07 mmol) in water (0.65 mL) and the reaction stirred for 5 minutes. Hydrogen peroxide (0.06 mL) was added and the reaction stirred for 2 hours. Saturated aqueous sodium sufite solution was added and the products extracted into ethyl acetate. The organic layer was dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with ethyl acetate, to give the title compound as a white solid (51 mg, 98%). (400 MHz, d6 DMSO): 8.15 (1H, s), 8.03 (4H, s), 7.96 (2H, d, J=8.5 Hz), 7.84 (3H, d, J=8.6 Hz), 7.61 (1H, s), 7.39 (2H, d, J=7.2 Hz), 7.33-7.27 (1H, m), 7.15 (1H, td, J=2.3, 8.6 Hz).

Workup

  1. stirringthe reaction stirred for 2 hours
  2. extractionthe products extracted into ethyl acetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography on silica
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-0cd1acac6d2342f89a0bfc0c25075888
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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