反応 #77537

反応方程式

1-(4-pyridyl)-2-imidazolidinone

sodium hydride

1-bromo-6-[4-(trifluoromethyl)-phenoxy]hexane

→

Compound 1

1-(4-pyridyl)-3-(6-[4-(trifluoromethyl)phenoxy]hexyl)-2-imidazolidinone

溶媒

DMF

DMF

反応条件

後処理

1. 1
   温度was cooled in an ice bath
2. 2
   workup.WAITAfter 5 minutes
3. 3
   その他the ice bath was removed
4. 4
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 3 hours
5. 5
   その他The reaction was quenched with a saturated aqueous ammonium chloride solution
6. 6
   抽出followed by extraction with a mixture of diethyl ether and ethyl acetate (3:1, 100 mL×3)
7. 7
   洗浄washed with brine
8. 8
   乾燥dried over magnesium sulfate
9. 9
   濃縮concentrated under reduced pressure
10. 10
    その他The crude mixture thus obtained
11. 11
    その他was purified with gradient chromatography [100% ethyl acetate
12. 12
    workup.ADDITIONsubsequently, a mixture of ethyl acetate and methanol (4:1)]

実験手順

A suspension of 1-(4-pyridyl)-2-imidazolidinone (0.10 g, 0.61 mmol) and sodium hydride (75% dispersion in mineral oil, 0.02 g, 0.67 mmol) in anhydrous DMF (7 mL) was cooled in an ice bath and stirred at 0° C. for 30 minutes, followed by addition of a solution of 1-bromo-6-[4-(trifluoromethyl)-phenoxy]hexane (0.20 g, 0.61 mmol) in anhydrous DMF (3 mL). After 5 minutes, the ice bath was removed and the reaction mixture was stirred at room temperature for 3 hours. The reaction was quenched with a saturated aqueous ammonium chloride solution followed by extraction with a mixture of diethyl ether and ethyl acetate (3:1, 100 mL×3). The organic layers were combined and washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The crude mixture thus obtained was purified with gradient chromatography [100% ethyl acetate, and, subsequently, a mixture of ethyl acetate and methanol (4:1)] to yield the product (i.e., Compound 1) as a white solid (0.18 g, 73%).

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