Water → HCID 66777044, compound

HRID 598752Notes

Reaction equation

HRID 598752 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:22]([F:25])([F:24])[F:23])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17](F)=[C:16]([CH3:21])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:32]([SH:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:22]([F:25])([F:24])[F:23])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([S:39][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[C:16]([CH3:21])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 58223544HCID 58223544, compound

Product 1

HCID 66777044HCID 66777044, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-(3,5-dichlorophenyl)-3-(4-fluoro-3-methylphenyl)-4,5-dihydro-5-(trifluoromethyl)isoxazole (i.e. the product from Step B of Example 2) (2.6 g, 6.65 mmol) and potassium carbonate (2.3 g, 16.6 mmol) in N,N-dimethylformamide (25 mL) was added benzyl mercaptan (0.782 mL, 6.65 mmol). The reaction mixture was heated at 90° C. for 4 h. The reaction mixture was then cooled and excess-water was added, and the mixture was extracted with ethyl acetate (2×100 mL). The organic extracts were dried (MgSO4) and concentrated under reduced pressure to provide a solid residue. The crude product was partially purified by silica gel column chromatography eluted with mixtures of hexane and ethyl acetate to afford a product containing the title compound (about 80% purity, 2.8 g).

Workup

  1. temperatureThe reaction mixture was then cooled
  2. extractionthe mixture was extracted with ethyl acetate (2×100 mL)
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customto provide a solid residue
  6. customThe crude product was partially purified by silica gel column chromatography
  7. washeluted with mixtures of hexane and ethyl acetate
  8. customto afford a product

Sources & evidence

ORD record
ord-d79c5fee198342078c208200989323e1
Source dataset
uspto-grants-2011_03
Patent number
US07897630B2

Reaction notes

Loading…