Sodium hydride → 1-[7-(4-Chlorophenoxy)heptyl]-3-(4-pyridyl)imidazolidin-2-one

HRID 49260Notes

Reaction equation

HRID 49260 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:11][CH2:10][NH:9][C:8]2=[O:12])=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1>CN(C)C=O>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:9]2[CH2:10][CH2:11][N:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[C:8]2=[O:12])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 37468181-Pyridin-4-yl-imidazolidin-2-oneHCID 129864911-Bromo-7-(4-chlorophenoxy)-heptane

Product 1

HCID 4930871-[7-(4-Chlorophenoxy)heptyl]-3-(4-pyridyl)imidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-pyridyl)-2-imidazolidinone (0.10 g, 0.62 mmol) dissolved in 10 mL dimethylformamide cooled in an ice bath was added NaH (60% dispersion in mineral oil, 27.2 mg, 0.68 mmol). The mixture was stirred at room temperature for 30 minutes then cooled in ice bath again. 1-Bromo-7-(4-chlorophenoxy)heptane (0.19 g, 0.62 mmol) was added, and the mixture was stirred at room temperature for additional 4 hours. The reaction was quenched with methanol, and the solvent was removed under reduced pressure. 5 mL of saturated aqueous NH4Cl solution and 10 mL dichloromethane were successively added to the residue. The dichloromethane layer was separated and dried over MgSO4, filtered, evaporated, and purified by column chromatography (ethyl acetate:MeOH=10:1) to give the product (i.e., Compound 2) as a white solid (0.15 g, 62%).

Workup

  1. temperaturecooled in an ice bath
  2. temperaturethen cooled in ice bath again
  3. stirringthe mixture was stirred at room temperature for additional 4 hours
  4. customThe reaction was quenched with methanol
  5. customthe solvent was removed under reduced pressure
  6. addition5 mL of saturated aqueous NH4Cl solution and 10 mL dichloromethane were successively added to the residue
  7. customThe dichloromethane layer was separated
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. custompurified by column chromatography (ethyl acetate:MeOH=10:1)

Sources & evidence

ORD record
ord-5525f22086724a0683b02fed2b2374e1
Source dataset
uspto-grants-2004_03
Patent number
US06706739B2

Reaction notes

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