반응 #77550

반응 방정식

[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

반응 조건

후처리

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

실험 절차

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%).

출처