Water → HCID 131736884, compound

HRID 55982Notes

Reaction equation

HRID 55982 reaction equation
[C:1]([O:5][N:6]=[C:7]([C:10]1[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[CH:12][N:11]=1)[CH2:8]Br)([CH3:4])([CH3:3])[CH3:2].[C:18]1(=[O:28])[NH:22][C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12.[K].O>CN(C)C=O>[Cl:16][C:15]1[C:10]([C:7](=[N:6][O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:8][N:22]2[C:21](=[O:23])[C:20]3=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]3[C:18]2=[O:28])=[N:11][CH:12]=[C:13]([Cl:17])[CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24194345Phthalimide potassium saltHCID 1180715072-bromo-1-(3,5-dichloropyridin-2-yl)ethanone-O-(tert-butyl)oxime

Product 1

HCID 131736884HCID 131736884, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 140 mg of 2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone-O-(tert-butyl)oxime in 2 ml of N,N-dimethylformamide, 91 mg of potassium phthalimide was added, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the reaction mixture was mixed with 10 ml of water and extracted with ethyl acetate (15 ml×1), the resulting organic layer was washed with water (10 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 2:8 to 4:6) as the eluent to obtain 162 mg of the desired product as a colorless resinous substance.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (15 ml×1)
  3. washthe resulting organic layer was washed with water (10 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-13c783c54bd7465ea689c55cb2448f39
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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