Phthalimide potassium salt → N-[[2-chloro-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]phenyl]methyl]phthalimide

HRID 1880235Notes

Reaction equation

HRID 1880235 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:13][C:12]([C:18]3[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[C:20]([Cl:26])[CH:19]=3)([C:14]([F:17])([F:16])[F:15])[O:11][N:10]=2)=[CH:5][C:4]=1[Cl:27].[C:28]1(=[O:38])[NH:32][C:31](=[O:33])[C:30]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:29]12.[K]>CN(C)C=O.C(OCC)(=O)C>[Cl:27][C:4]1[CH:5]=[C:6]([C:9]2[CH2:13][C:12]([C:18]3[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[C:20]([Cl:26])[CH:19]=3)([C:14]([F:17])([F:16])[F:15])[O:11][N:10]=2)[CH:7]=[CH:8][C:3]=1[CH2:2][N:32]1[C:31](=[O:33])[C:30]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:29]2[C:28]1=[O:38]

Participants

5

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 867616893-(4-Bromomethyl-3-chlorophenyl)-5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

Product 1

HCID 86761690N-[[2-chloro-4-[5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]phenyl]methyl]phthalimide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 34.1 g of 3-(4-bromomethyl-3-chlorophenyl)-5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 200 mL of N,N-dimethylformamide, 12.6 g of potassium phthalimide was added and the resultant mixture was stirred at room temperature for 3 hours. After the completion of the reaction, the reaction mixture was diluted with 350 mL of ethyl acetate and the diluted reaction mixture was washed with water (80 mL×3). Subsequently, the washed reaction mixture was dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:3) to obtain 24.3 g of the objective substance as a light yellow resinoid.

Workup

  1. customAfter the completion of the reaction
  2. customthe diluted reaction mixture
  3. washwas washed with water (80 mL×3)
  4. customSubsequently, the washed reaction mixture
  5. dry with materialdried over saturated saline and anhydrous sodium sulfate in this order
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resultant residue was purified by silica gel column chromatography
  8. washeluting with ethyl acetate-hexane (1:3)
  9. customto obtain 24.3 g of the objective substance as a light yellow resinoid

Sources & evidence

ORD record
ord-141418519cdf4015a24f8d9467b342a1
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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