Water → HCID 11517731, compound

HRID 1173478Notes

Reaction equation

HRID 1173478 reaction equation
[C:1]1([S:7][CH2:8][CH2:9][N:10]([CH2:23][C:24]([F:27])([F:26])[F:25])[C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([C:19]([F:22])([F:21])[F:20])[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:28]OS([O-])=O.[K+].[OH2:34]>CO>[C:1]1([S:7]([CH2:8][CH2:9][N:10]([CH2:23][C:24]([F:27])([F:25])[F:26])[C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([C:19]([F:20])([F:21])[F:22])[CH:12]=2)(=[O:28])=[O:34])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11538670HCID 11538670, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 11517731HCID 11517731, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An ice-cold solution of 4-[[2-(phenylthio)ethyl](2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (0.056 g, 0.138 mmol) in MeOH (6 mL) was treated with a solution of oxone (0.255 g, 0.415 mmol) in water (3 mL) and stirred at rt. After 1.5 h, the mixture was partitioned between EtOAc and water. The organic phase was washed with water and brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (5-50% EtOAc/hexanes gradient) and the product crystallized from CH2Cl2/hexanes to give the title compound as a white solid (0.057 g, 95% yield): MS (ES) m/z 437 (M+1).

Workup

  1. customthe mixture was partitioned between EtOAc and water
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (5-50% EtOAc/hexanes gradient)
  6. customthe product crystallized from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-acafe5bad6c441d1afa2d9fae6ba65f2
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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