Réaction #77550

Équation de réaction

[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

Conditions de réaction

Traitement

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

Mode opératoire

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%).

Source