Reaktion #77550

Reaktionsgleichung

[5-phenyl-1-(4-pyridyl)tetrahydro-1H-2-imidazolyliden] aminomethane-nitrile

sodium hydride

DMF

1-[(6-bromohexyl)oxy]-4-bromobenzene

DMF

→

Compound 15

1-[6-(4-bromophenoxy)hexyl]-4-phenyl-3-(4-pyridyl)-2-imidazolidinone

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGThe resulting mixture was stirred
3. 3
   Temperaturheated at 80° C. for 16 hours
4. 4
   SonstigeThe reaction was quenched with water and aqueous solution
5. 5
   Extraktionwas extracted with ether (3×20 mL)
6. 6
   Waschenwashed with NaCl(sat.)
7. 7
   Trocknendried over MgSO4
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   Sonstigeto give the crude residue, which
10. 10
    Sonstigewas subjected to purification by chromatography elution with ethyl acetate and methanol (20:1)

Vorschrift

To a solution of [5-phenyl-1-(4-pyridyl)tetrahydro-1H-2-imidazolyliden] aminomethane-nitrile (0.1 g, 0.38 mmol) in 6 mL of DMF at 0° C. was added sodium hydride (75% dispersion in mineral oil, 24 mg) in one portion. The mixture was stirred at room temperature for 20 min and then 1-[(6-bromohexyl)oxy]-4-bromobenzene (192 mg, 0.57 mmol) dissolved in DMF (4 mL) was added dropwise. The resulting mixture was stirred and heated at 80° C. for 16 hours. The reaction was quenched with water and aqueous solution was extracted with ether (3×20 mL). The organic layers were combined, washed with NaCl(sat.), dried over MgSO4, and concentrated under reduced pressure to give the crude residue, which was subjected to purification by chromatography elution with ethyl acetate and methanol (20:1) to afford the product (i.e., Compound 15) as a white solid (90 mg, 45%).

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