Chlorosuccinimide → 3-(3-Chloro-4-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole

HRID 551312Notes

Reaction equation

HRID 551312 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[CH:5]=[N:6][OH:7].ClN1C(=O)CCC1=O.[Cl:20][C:21]1[CH:22]=[C:23]([C:28]([C:30]([F:33])([F:32])[F:31])=[CH2:29])[CH:24]=[C:25]([Cl:27])[CH:26]=1.C(=O)([O-])O.[K+]>COCCOC.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[CH2:29][C:28]([C:23]3[CH:24]=[C:25]([Cl:27])[CH:26]=[C:21]([Cl:20])[CH:22]=3)([C:30]([F:31])([F:33])[F:32])[O:7][N:6]=2)[CH:8]=[CH:9][C:10]=1[CH3:11]

Participants

8

Reactant 4

HCID 31398ChlorosuccinimideHCID 516893Potassium BicarbonateHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 730143123-Chloro-4-methylbenzaldoxime

Product 1

HCID 866315493-(3-Chloro-4-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazoleYield 72%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

In a solution of 10.6 g of 3-chloro-4-methylbenzaldoxime in 60 mL of 1,2-dimethoxyethane, 9.2 g of N-chlorosuccinimide was added, and stirred at 70° C. for 2 hours. Then, the reaction mixture was left and cooled to room temperature, 11.3 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1 of Synthetic Example 1, 15.6 g of potassium hydrogen carbonate and 10 mL of water were added, and continued to stir at room temperature further for 20 hours. After the completion of the reaction, the reaction mixture was diluted with 70 mL of ethyl acetate, washed with water (50 mL×1), and dehydrated with and dried over saturated sodium chloride aqueous solution and anhydrous sodium sulfate in that order, and then the solvent was distilled off under reduced pressure. The residual solid was washed with diisopropyl ether to obtain 13.8 g of the aimed product as white crystal.

Workup

  1. waitThen, the reaction mixture was left
  2. temperaturecooled to room temperature
  3. stirringto stir at room temperature further for 20 hours
  4. customAfter the completion of the reaction
  5. washwashed with water (50 mL×1)
  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. washThe residual solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-68193f8ee7db4996bafaf6482acd84c0
Source dataset
uspto-grants-2011_05
Patent number
US07947715B2

Reaction notes

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