Réaction #77543

Équation de réaction

1-Bromo-4-[(7-bromoheptyl)oxy] benzene

1-(2-chloro-4-pyridyl)-2-imidazolidinone

NaH

→

Compound 8

1-[7-(4-bromophenoxy)heptyl]-3-(2-chloro-4-pyridyl)-2-imidazolidinone

Solvants

dimethylformamide

Conditions de réaction

Traitement

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

Mode opératoire

To a solution of 1-(2-chloro-4-pyridyl)-2-imidazolidinone (0.12 g, 0.63 mmol) dissolved in 10 mL dimethylformamide at 0° C. was added NaH (60% dispersion in mineral oil, 27.7 mg, 0.69 mmol). The mixture was stirred at room temperature for 30 minutes; then cooled in ice bath. 1-Bromo-4-[(7-bromoheptyl)oxy] benzene (0.22 g, 0.63 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. A saturated aqueous NH4Cl solution (5 mL) and dichloromethane (10 mL) 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 8) as a white solid (0.19 g, 64%).

Source