Sodium hydride → 1-[6-(4-Bromophenoxy)hexyl]-3-(4-fluorophenyl)-2-imidazolidinone

HRID 49264Notes

Reaction equation

HRID 49264 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][NH:10][C:9]2=[O:13])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][CH:26]=1)C>CN(C)C=O>[Br:31][C:28]1[CH:29]=[CH:30][C:25]([O:24][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][N:10]2[CH2:11][CH2:12][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:9]2=[O:13])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 14807851-(4-Fluorophenyl)imidazolidin-2-oneHCID 20636597HCID 20636597, compound

Product 1

HCID 129864871-[6-(4-Bromophenoxy)hexyl]-3-(4-fluorophenyl)-2-imidazolidinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-2-imidazolidinone (0.12 g, 0.65 mmol) dissolved in 10 mL dimethylformamide cooled in an ice bath was added NaH (60% dispersion in mineral oil, 39.0 mg, 0.98 mmol). The mixture was stirred at room temperature for 30 minutes and then cooled in ice bath. 1-Bromo-6-(4-bromophenoxy)heptane (0.22 g, 0.65 mmol) was added, and the mixture was stirred at room temperature for additional 4 hours. The reaction was quenched with methanol, and the solvents were removed under reduced pressure. 5 mL of saturated NH4Cl water solution and 10 mL of dichloromethane were added to the residue. The dichloromethane layer was dried over MgSO4, filtered, evaporated, and purified by column chromatography (ethyl acetate:MeOH=10:1) to give the product (i.e., Compound 7) as a white solid (0.14 g, 48%).

Workup

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

Sources & evidence

ORD record
ord-7070ec48c1e54d5e9696f57c6b0256e5
Source dataset
uspto-grants-2004_03
Patent number
US06706739B2

Reaction notes

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