Réaction #77544

Équation de réaction

1-Bromo-4-[(5-bromopentyl)oxy] benzene

1-phenyl-2-imidazolidinone

NaH

→

Compound 9

1-[5-(4-bromophenoxy)pentyl]-3-phenyl-2-imidazolidinone

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   Températurecooled in an ice bath
2. 2
   Températurethen cooled in ice bath
3. 3
   workup.STIRRINGthe mixture was stirred at room temperature for additional 4 hours
4. 4
   AutreThe reaction was quenched with MeOH
5. 5
   workup.ADDITIONSaturated aqueous NH4Cl and dichloromethane (15 mL) were added to the residue
6. 6
   AutreThe dichloromethane layer was separated
7. 7
   Séchagedried over MgSO4
8. 8
   Filtrationfiltered
9. 9
   Autreevaporated
10. 10
    Autrepurified by column chromatography (ethyl acetate:MeOH=10:1)

Mode opératoire

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%).

Source