Water → 5-[5-(3,5-Dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-(methylthio)benzonitrile

HRID 598754Notes

Reaction equation

HRID 598754 reaction equation
[CH3:1][S-:2].[Na+].C(=O)([O-])[O-].[K+].[K+].[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2([C:32]([F:35])([F:34])[F:33])[O:22][N:21]=[C:20]([C:23]3[CH:24]=[CH:25][C:26](F)=[C:27]([CH:30]=3)[C:28]#[N:29])[CH2:19]2)[CH:14]=[C:15]([Cl:17])[CH:16]=1.O>CN(C)C=O>[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2([C:32]([F:35])([F:34])[F:33])[O:22][N:21]=[C:20]([C:23]3[CH:24]=[CH:25][C:26]([S:2][CH3:1])=[C:27]([CH:30]=3)[C:28]#[N:29])[CH2:19]2)[CH:14]=[C:15]([Cl:17])[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 4378561Sodium methanethiolate2×HCID 716156875-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-fluorobenzonitrile

Product 1

HCID 667782265-[5-(3,5-Dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-(methylthio)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium thiomethoxide (0.21 g, 3 mmol) and potassium carbonate (0.28 g, 2 mmol) in 4 mL of N,N-dimethylformamide was added a solution of 5-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-fluorobenzonitrile (prepared by a method similar to Example 2, Step A and Step B; 1.00 g, 2.48 mmol) in N,N-dimethylformamide (6 mL). This mixture was stirred at ambient temperature for 1 h. Then an additional portion of sodium thiomethoxide (0.21 g, 3 mmol) was added. After an additional 15 minutes, water was added, and the mixture was successively extracted with diethyl ether and ethyl acetate. The organic extracts were combined and washed several times with water and saturated aqueous sodium chloride solution, and then dried over magnesium sulfate, and concentrated to leave an off-white solid. The solid was triturated with a mixture of diethyl ether and hexanes, collected on a glass frit, and dried in air to afford the title compound, a compound of the present invention, as a white solid (1.04 g).

Workup

  1. customprepared by a method similar to Example 2, Step A and Step B
  2. waitAfter an additional 15 minutes
  3. extractionthe mixture was successively extracted with diethyl ether and ethyl acetate
  4. washwashed several times with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto leave an off-white solid
  8. customThe solid was triturated with a mixture of diethyl ether and hexanes
  9. customcollected on a glass frit
  10. customdried in air

Sources & evidence

ORD record
ord-7f23800254af4f1bbebefad055791c5f
Source dataset
uspto-grants-2011_03
Patent number
US07897630B2

Reaction notes

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