Sodium hydride → 1-[5-(4-Bromophenoxy)pentyl]-3-phenyl-2-imidazolidinone

HRID 49266Notes

Reaction equation

HRID 49266 reaction equation
[C:1]1([N:7]2[CH2:11][CH2:10][NH:9][C:8]2=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br)=[CH:18][CH:17]=1>CN(C)C=O>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:9]2[CH2:10][CH2:11][N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]2=[O:12])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2552731-Phenylimidazolidin-2-oneHCID 20636596HCID 20636596, compound

Product 1

HCID 4931231-[5-(4-Bromophenoxy)pentyl]-3-phenyl-2-imidazolidinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-phenyl-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, 27.0 mg, 0.68 mmol). The mixture was stirred at room temperature for 30 minutes; then cooled in ice bath. 1-Bromo-4-[(5-bromopentyl)oxy] benzene (0.20 g, 0.62 mmol) was added, and the mixture was stirred at room temperature for additional 4 hours. The reaction was quenched with MeOH, and the solvents were pumped off. Saturated aqueous NH4Cl and dichloromethane (15 mL) were 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 9) as a yellow solid (0.19 g, 77%).

Workup

  1. temperaturecooled in an ice bath
  2. temperaturethen cooled in ice bath
  3. stirringthe mixture was stirred at room temperature for additional 4 hours
  4. customThe reaction was quenched with MeOH
  5. additionSaturated aqueous NH4Cl and dichloromethane (15 mL) were added to the residue
  6. customThe dichloromethane layer was separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. custompurified by column chromatography (ethyl acetate:MeOH=10:1)

Sources & evidence

ORD record
ord-a5430ede399f4981bf7d1b1b95c3af5e
Source dataset
uspto-grants-2004_03
Patent number
US06706739B2

Reaction notes

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