Sodium hydride → 1-(4-Chlorophenyl)-3-(5-[3-(4-methoxyphenoxy)propoxy]pentyl)-2-imidazolidinone

HRID 49263Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 49263
[Cl: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][O:22][CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][CH2:11][N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][CH2:25][O:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[C:9]2=[O:13])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 264512-Imidazolidinone, 1-(p-chlorophenyl)-HCID 20636584HCID 20636584, Verbindung

Produkt 1

HCID 129864861-(4-Chlorophenyl)-3-(5-[3-(4-methoxyphenoxy)propoxy]pentyl)-2-imidazolidinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-chlorophenyl)-2-imidazolidinone (0.10 g, 0.53 mmol) dissolved in 10 mL dimethylformamide cooled in an ice bath was added NaH (60% dispersion in mineral oil, 27.3 mg, 0.80 mmol). The mixture was stirred at room temperature for 30 min and then cooled in ice bath. 1-{3-[(5-Bromopentyl)oxy]propoxy}-4-methoxybenzene (0.18 g, 0.53 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. 5 mL 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 6) as a white solid (0.16 g, 68%).

Aufarbeitung

  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 MeOH
  5. addition5 mL saturated aqueous NH4Cl solution and 10 mL dichloromethane were successively 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)

Quellen und Nachweise

ORD-Eintrag
ord-9a4491e1858b469db7faea809a060b80
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706739B2

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