Reaktion #77545

Reaktionsgleichung

1-Bromo-4-[(6-bromohexyl)oxy] benzene

1-(4-methyl-1,3-thiazol-2-yl)-2-imidazolidinone

NaH

→

Compound 10

1-[6-(4-bromophenoxy)hexyl]-3-(4-methyl-1,3-thiazol-2-yl)-2-imidazolidinone

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled in ice bath
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for additional 4 hours
3. 3
   SonstigeThe reaction was quenched with methanol
4. 4
   Sonstigethe solvents were removed under reduced pressure
5. 5
   workup.ADDITIONA saturated aqueous NH4Cl solution and dichloromethane were successively added to the residue
6. 6
   SonstigeThe dichloromethane layer was separated
7. 7
   Trocknendried over MgSO4
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated
10. 10
    Sonstigepurified by column chromatography (ethyl acetate:MeOH=10:1)

Vorschrift

To a suspension of 1-(4-methyl-1,3-thiazol-2-yl)-2-imidazolidinone (0.11 g, 0.61 mmol) dissolved in 10 mL of dimethylformamide at 0° C. was added NaH (60% dispersion in mineral oil, 36.6 mg, 0.92 mmol). The mixture was stirred at room temperature for 30 minutes and then cooled in ice bath. 1-Bromo-4-[(6-bromohexyl)oxy] benzene (0.21 g, 0.61 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. A saturated aqueous NH4Cl solution and 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 10) as a yellow viscous oil (0.19 g, 74%).

Quelle