Dichloromethane → HCID 86631548, compound

HRID 885793Notes

Reaction equation

HRID 885793 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]([CH2:20]O)=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl:26]CCl>S(Cl)(Cl)=O.CN(C)C=O>[Cl:26][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([C:11]2[CH2:10][C:9]([C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)([C:22]([F:25])([F:24])[F:23])[O:13][N:12]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 67188704HCID 67188704, compound

Product 1

HCID 86631548HCID 86631548, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 24386Thionyl ChlorideSolvent

Procedure

In a solution of 4.2 g of 5-(3,5-dichlorophenyl)-3-[4-(hydroxymethyl)phenyl]-5-trifluoromethyl-4,5-dihydro-isoxazole in 100 mL of dichloromethane, 1.2 mL of thionyl chloride and a catalytic amount (2 to 3 drops) of N,N-dimethylformamide were added, and stirred under reflux with heating for 3 hours. After the completion of the reaction, the reaction mixture was poured into 30 mL of ice water, the organic phase was collected, washed with water (50 mL×1) and saturated sodium hydrogen carbonate aqueous solution (30 mL×3), and thereafter dehydrated with and dried over saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluted with ethyl acetate-hexane (1:5) to obtain 4.1 g of the aimed product as pale yellow crystal.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating for 3 hours
  3. customAfter the completion of the reaction
  4. customthe organic phase was collected
  5. washwashed with water (50 mL×1) and saturated sodium hydrogen carbonate aqueous solution (30 mL×3)
  6. dry with materialdried over saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified with silica gel column chromatography that
  9. washwas eluted with ethyl acetate-hexane (1:5)

Sources & evidence

ORD record
ord-f058df038fd741c7a96188c79a9238cc
Source dataset
uspto-grants-2012_08
Patent number
US08242283B2

Reaction notes

Loading…