Triethylamine → 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxyphen yl trifluoromethane sulfonate

HRID 1844813Notes

Reaction equation

HRID 1844813 reaction equation
[F:1][C:2]([F:19])([F:18])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[N:14][OH:15])=[CH:9][C:8]=1[O:16][CH3:17])(=[O:5])=[O:4].ClN1C(=O)CCC1=O.[Cl:28][C:29]1[CH:30]=[C:31]([C:36]([C:38]([F:41])([F:40])[F:39])=[CH2:37])[CH:32]=[C:33]([Cl:35])[CH:34]=1.C(N(CC)CC)C>CN(C)C=O>[F:19][C:2]([F:18])([F:1])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:37][C:36]([C:31]3[CH:32]=[C:33]([Cl:35])[CH:34]=[C:29]([Cl:28])[CH:30]=3)([C:38]([F:39])([F:41])[F:40])[O:15][N:14]=2)=[CH:9][C:8]=1[O:16][CH3:17])(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 871503954-Hydroxyiminomethyl-2-methoxyphenyl trifluoromethane sulfonate

Product 1

HCID 231598024-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxyphen yl trifluoromethane sulfonateYield 41.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

In a solution of 2.0 g of 4-hydroxyiminomethyl-2-methoxyphenyl trifluoromethane sulfonate in 30 ml of N,N-dimethylformamide, 0.9 g of N-chlorosuccinic acid imide was added, and stirred at 40 to 50° C. for 30 minutes. Then, the reaction mixture was left and cooled to room temperature, 1.5 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1 of Synthetic Example 3 and 0.7 g of triethylamine were added, and stirred at room temperature for 90 minutes. After the completion of the reaction, the reaction mixture was poured in 100 ml of ice water, extracted with ethyl acetate (50 ml×2), the organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:7), and 1.4 g of the aimed product was obtained as colorless resinous substance.

Workup

  1. waitThen, the reaction mixture was left
  2. temperaturecooled to room temperature
  3. stirringstirred at room temperature for 90 minutes
  4. customAfter the completion of the reaction
  5. extractionextracted with ethyl acetate (50 ml×2)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-5352fdef1ab44f5ab7c572fcfbd39983
Source dataset
uspto-grants-2015_02
Patent number
US08946492B2

Reaction notes

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