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

HRID 910342Notes

Reaction equation

HRID 910342 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[N:11][OH:12])=[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>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:31][C:30]([C:25]3[CH:26]=[C:27]([Cl:29])[CH:28]=[C:23]([Cl:22])[CH:24]=3)([C:32]([F:33])([F:35])[F:34])[O:12][N:11]=2)=[CH:6][CH:5]=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 4-(hydroxyiminomethyl)benzoic acid methyl ester in 15 ml of N,N-dimethylformamide, 2.04 g of N-chlorosuccinic acid imide 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, continued to stir at room temperature 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, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residual solid was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:1 to 1:3 gradient), and 4.05 g of the aimed product was obtained as white crystal.

Workup

  1. temperatureThen, the reaction mixture was cooled to 0° C.
  2. stirringto stir at room temperature 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 anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residual solid was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that
  9. washwas eluted with ethyl acetate-hexane (1:1 to 1:3 gradient)

Sources & evidence

ORD record
ord-a6162049df1d4b5797e3484414c15b1b
Source dataset
uspto-grants-2011_09
Patent number
US08022089B2

Reaction notes

Loading…