Potassium Carbonate → HCID 66778453, compound

HRID 1520408Notes

Reaction equation

HRID 1520408 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:13]([C:14]([F:17])([F:16])[F:15])[O:12][N:11]=[C:10]2[C:18]2[CH:19]=[CH:20][C:21](SC)=[C:22]([CH:25]=2)[C:23]#[N:24])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl[C:29]1C=C(C=CC=1)C(OO)=O.[S:39](=[O:42])(O)[O-:40].[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:13]([C:14]([F:16])([F:15])[F:17])[O:12][N:11]=[C:10]2[C:18]2[CH:19]=[CH:20][C:21]([S:39]([CH3:29])(=[O:42])=[O:40])=[C:22]([CH:25]=2)[C:23]#[N:24])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 66777553HCID 66777553, compound

Product 1

HCID 66778453HCID 66778453, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-(methylthio)benzonitrile (i.e. the product of Example 5) (0.42 g, 1.0 mmol) in 20 mL of dichloromethane was added 3-chloroperoxybenzoic acid (0.90 g of ˜77% peracid, 4.0 mmol) in one portion, and the mixture was stirred at ambient temperature overnight. Aqueous sodium bisulfite solution was added, and after several minutes solid potassium carbonate was added. The layers were separated, and the organic phase was dried over magnesium sulfate and concentrated to leave a 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 product, a compound of the present invention, as a white solid (0.38 g).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customto leave a solid
  5. customThe solid was triturated with a mixture of diethyl ether and hexanes
  6. customcollected on a glass frit
  7. customdried in air

Sources & evidence

ORD record
ord-ccdff262e9c74a12a334dd5937e3c81a
Source dataset
uspto-grants-2015_07
Patent number
US09073910B2

Reaction notes

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