Methanol → HCID 11633134, compound

HRID 1173477Notes

Reaction equation

HRID 1173477 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.C[OH:29]>O>[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:29])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 887Methanol2×HCID 11538670HCID 11538670, compound

Product 1

HCID 11633134HCID 11633134, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 4-[[2-(phenylthio)ethyl](2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (0.039 g, 0.096 mmol) in MeOH (3 mL) was added a solution of NaIO4 (0.041 g, 0.193 mmol) in water (1 mL) and stirred at rt. After 1 h, additional NaIO4 (0.041 g, 0.19 mmol) dissolved in water (1 mL) was added and the reaction mixture diluted with MeOH (1 mL). After stirring at rt for 12 h, the mixture was partitioned between EtOAc and brine. The organic phase was washed with water and brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (1-10% MeOH/CH2Cl2 gradient) to give the title compound (0.037 g, 88% yield): MS (ES) m/z 421 (M+1).

Workup

  1. additionwas added
  2. stirringAfter stirring at rt for 12 h
  3. customthe mixture was partitioned between EtOAc and brine
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (1-10% MeOH/CH2Cl2 gradient)

Sources & evidence

ORD record
ord-9d16efafb0c343e0bcd952ce877c02ca
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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