Sodium Iodide → 2-{4-[5-(3,5-Dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-benzyl}-isoindole-1,3-dione

HRID 405704Notes

Reaction equation

HRID 405704 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH3:26])[O:11][C:12]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=3)([C:14]([F:17])([F:16])[F:15])[CH:13]=2)=[CH:5][C:4]=1[CH3:27].[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].[I-].[Na+].CCCCCC>CN(C)C=O.O>[Cl:25][C:20]1[CH:19]=[C:18]([C:12]2([C:14]([F:15])([F:17])[F:16])[O:11][N:10]([CH3:26])[C:9]([C:6]3[CH:7]=[CH:8][C:3]([CH2:2][N:32]4[C:28](=[O:38])[C:29]5[C:30](=[CH:34][CH:35]=[CH:36][CH:37]=5)[C:31]4=[O:33])=[C:4]([CH3:27])[CH:5]=3)=[CH:13]2)[CH:23]=[C:22]([Cl:24])[CH:21]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8058HexaneHCID 24194345Phthalimide potassium saltHCID 53371510HCID 53371510, compound

Product 1

HCID 533715112-{4-[5-(3,5-Dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-benzyl}-isoindole-1,3-dioneYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

524 mg of 3-(4-Chloromethyl-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazole, 216 mg of potassium phthalimide and 10 mg sodium iodide in 7 ml N,N-dimethylformamide were stirred at ambient temperature overnight. The mixture was diluted with water (100 ml) and extracted with 200 ml of ether. The organic phase was washed with water and dried. Evaporation of the solvent afforded a foam. Trituration with hexane gave 2-{4-[5-(3,5-Dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-benzyl}-isoindole-1,3-dione as a white solid in 98% yield. 1H-NMR (CDCl3, δ in ppm): 7.88 (m, 2H), 7.75 (m, 2H), 7.22-7.43 (m, 6H), 5.30 (s, 1H), 4.86 (s, 2H), 2.96 (s, 3H), 2.50 (s, 3H).

Workup

  1. extractionextracted with 200 ml of ether
  2. washThe organic phase was washed with water
  3. customdried
  4. customEvaporation of the solvent
  5. customafforded a foam

Sources & evidence

ORD record
ord-63ffad0637a44e57b601922de6217b47
Source dataset
uspto-grants-2014_06
Patent number
US08754053B2

Reaction notes

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