Реакция #77550

Уравнение реакции

[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

Условия реакции

Обработка

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

Методика

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%).

Источник