Water → N-[2-(3,5-dichloropyridin-2-yl)-2-(propoxyimino)ethyl]phthalimide

HRID 55986Notes

Reaction equation

HRID 55986 reaction equation
[Cl:1][C:2]1[C:3]([C:9](=[N:22][OH:23])[CH2:10][N:11]2[C:15](=[O:16])[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:21])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:31][CH2:32][CH3:33].O>CN(C)C=O>[Cl:1][C:2]1[C:3]([C:9](=[N:22][O:23][CH2:31][CH2:32][CH3:33])[CH2:10][N:11]2[C:12](=[O:21])[C:13]3=[CH:20][CH:19]=[CH:18][CH:17]=[C:14]3[C:15]2=[O:16])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 136987064N-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]phthalimide

Product 1

HCID 118071539N-[2-(3,5-dichloropyridin-2-yl)-2-(propoxyimino)ethyl]phthalimideYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 265 mg of N-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]phthalimide in 2 ml of N,N-dimethylformamide, 310 mg of potassium carbonate and 387 mg of 1-iodopropane were added, and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the reaction mixture was mixed with 30 ml of water and extracted with ethyl acetate (50 ml×1), the resulting organic layer was washed with water (50 ml×1) and 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 15:85 to 25:75) as the eluent to obtain 235 mg of the desired product as a yellow resinous substance.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (50 ml×1)
  3. washthe resulting organic layer was washed with water (50 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-0d347aef2e154005be744f8d1f13d25a
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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