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

HRID 55984Notes

Reaction equation

HRID 55984 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[CH:7][N:6]=1)=[O:4].[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.[K].O>CN(C)C=O>[Cl:11][C:10]1[C:5]([C:3](=[O:4])[CH2:2][N:17]2[C:16](=[O:18])[C:15]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]3[C:13]2=[O:23])=[N:6][CH:7]=[C:8]([Cl:12])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24194345Phthalimide potassium saltHCID 534166072-Bromo-1-(3,5-dichloropyridin-2-yl)ethanone

Product 1

HCID 118071534N-[2-(3,5-dichloropyridin-2-yl)-2-oxoethyl]phthalimideYield 8.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 3.00 g of the 2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone prepared in Step 2 in Synthetic Example 2 in 30 ml of N,N-dimethylformamide, 4.13 g of potassium phthalimide was added, and the mixture was stirred at 80° C. for 3 hours and then at room temperature for 18 hours. After completion of the reaction, the reaction mixture was mixed with 150 ml of water and extracted with ethyl acetate (50 ml×2), the resulting organic layers were combined, 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 mixed with 40 ml of a mixture of diisopropyl ether and hexane (1:1), the insolubles were filtered off, 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 0.32 g of the desired product as a dark brown resinous substance.

Workup

  1. waitat room temperature for 18 hours
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate (50 ml×2)
  4. washwashed with water (50 ml×1)
  5. dry with materialdried over saturated aqueous sodium chloride
  6. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
  7. additionThe resulting residue was mixed with 40 ml of a mixture of diisopropyl ether and hexane (1:1)
  8. filtrationthe insolubles were filtered off
  9. customthe solvent was evaporated under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b82965e1a9e349b69f71fb8e4ffa5f93
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

Loading…