反応 #77550

反応方程式

[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

反応条件

後処理

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGThe resulting mixture was stirred
3. 3
   温度heated at 80° C. for 16 hours
4. 4
   その他The reaction was quenched with water and aqueous solution
5. 5
   抽出was extracted with ether (3×20 mL)
6. 6
   洗浄washed with NaCl(sat.)
7. 7
   乾燥dried over MgSO4
8. 8
   濃縮concentrated under reduced pressure
9. 9
   その他to give the crude residue, which
10. 10
    その他was subjected to purification by chromatography elution with ethyl acetate and methanol (20:1)

実験手順

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%).

出典