Water → N-[2-(3,5-dichloropyridin-2-yl)-1-methyl-2-oxoethyl)phthalimide

HRID 55997Notes

Reaction equation

HRID 55997 reaction equation
Br[CH:2]([CH3:13])[C:3]([C:5]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[CH:7][N:6]=1)=[O:4].[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K].O>CN(C)C=O>[Cl:11][C:10]1[C:5]([C:3](=[O:4])[CH:2]([N:18]2[C:17](=[O:19])[C:16]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]3[C:14]2=[O:24])[CH3:13])=[N:6][CH:7]=[C:8]([Cl:12])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24194345Phthalimide potassium saltHCID 1180715622-Bromo-1-(3,5-dichloropyridin-2-yl)-1-propanone

Product 1

HCID 118071579N-[2-(3,5-dichloropyridin-2-yl)-1-methyl-2-oxoethyl)phthalimideYield 32.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5.00 g of 2-bromo-1-(3,5-dichloropyridin-2-yl)-1-propanone in 20 ml of N,N-dimethylformamide, 3.27 g of potassium phthalimide was added, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was mixed with 50 ml of water and extracted with ethyl acetate (50 ml×2), and the resulting organic layers were combined, washed with water (30 ml×1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 2.02 g of the desired crude product as brown crystals. The crystals were used in the next step without further purification.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (50 ml×2)
  3. washwashed with water (30 ml×1)
  4. dry with materialdried over saturated aqueous sodium chloride
  5. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9dd1417c96a740a0a0cfacf3811df5ce
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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