Water → N-[2-(2,4-dichlorophenyl)-2-(methoxyimino)ethyl]phthalimide

HRID 55973Notes

Reaction equation

HRID 55973 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[Cl:14])[CH2:5]Br.[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.[K].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:14][C:8]1[CH:9]=[C:10]([Cl:13])[CH:11]=[CH:12][C:7]=1[C:4](=[N:3][O:2][CH3:1])[CH2:5][N:19]1[C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]2[C:15]1=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 24194345Phthalimide potassium saltHCID 1180716162-bromo-1-(2,4-dichlorophenyl)ethanone-O-methyloxime

Product 1

HCID 118071602N-[2-(2,4-dichlorophenyl)-2-(methoxyimino)ethyl]phthalimideYield 79.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2.17 g of 2-bromo-1-(2,4-dichlorophenyl)ethanone-O-methyloxime in 20 ml of N,N-dimethylformamide, 3.03 g of potassium phthalimide and 1.61 g of potassium carbonate were added, and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the reaction mixture was mixed with 40 ml of water and extracted with ethyl acetate (50 ml×1), the resulting organic layer was washed with water (20 ml×1) and then dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 1:9 to 3:7) as the eluent to obtain 2.10 g of the desired product as pale yellow crystals.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (50 ml×1)
  3. washthe resulting organic layer was washed with water (20 ml×1)
  4. dry with materialdried over saturated aqueous sodium chloride
  5. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c7e38a2a4cfe4577b970b6e0f7a09925
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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