Triethylamine → Methyl 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoate

HRID 885792Notes

Reaction equation

HRID 885792 reaction equation
[OH:1][N:2]=[CH:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.ClN1C(=O)CCC1=O.[Cl:22][C:23]1[CH:24]=[C:25]([C:30]([C:32]([F:35])([F:34])[F:33])=[CH2:31])[CH:26]=[C:27]([Cl:29])[CH:28]=1.C(N(CC)CC)C>CN(C)C=O>[Cl:22][C:23]1[CH:24]=[C:25]([C:30]2([C:32]([F:35])([F:33])[F:34])[O:1][N:2]=[C:3]([C:4]3[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=3)[CH2:31]2)[CH:26]=[C:27]([Cl:29])[CH:28]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 6804457Methyl 4-(hydroxyiminomethyl)benzoateHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

Product 1

HCID 66785507Methyl 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoateYield 68.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

In a solution of 2.70 g of methyl 4-(hydroxyiminomethyl)benzoate in 15 mL of N,N-dimethylformamide, 2.04 g of N-chlorosuccinimide was added, and stirred at 40° C. for 40 minutes. Then, the reaction mixture was cooled to 0° C., 3.40 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene and 1.72 g of triethylamine were added, and continued to stir at room temperature further for 18 hours. After the completion of the reaction, the reaction mixture was poured into 100 mL of ice water, extracted with ethyl acetate (50 mL×2), the organic phase was washed with water and then 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 residual solid was purified with medium pressure preparative liquid chromatography (medium pressure collection apparatus: YFLC-Wprep manufactured by Yamazen Corporation) that was eluted with ethyl acetate-hexane (gradient of 1:1 to 1:3) to obtain 4.05 g of the aimed products as white crystal.

Workup

  1. temperatureThen, the reaction mixture was cooled to 0° C.
  2. stirringto stir at room temperature further for 18 hours
  3. customAfter the completion of the reaction
  4. extractionextracted with ethyl acetate (50 mL×2)
  5. washthe organic phase was washed with water
  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 residual solid was purified with medium pressure preparative liquid chromatography (medium pressure collection apparatus: YFLC-Wprep manufactured by Yamazen Corporation) that
  9. washwas eluted with ethyl acetate-hexane (gradient of 1:1 to 1:3)

Sources & evidence

ORD record
ord-762a43aa49f34bbb9b0cd79d2aefeb24
Source dataset
uspto-grants-2012_08
Patent number
US08242283B2

Reaction notes

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