반응 #167287

반응 방정식

1-naphthalen-2-yl-imidazolidin-2-one

trans-1,2-diamino cyclohexane

potassium carbonate

3-bromo-5-trifluoromethyl-pyridine

→

1-naphthalen-2-yl-3-(5-trifluoromethyl-pyridin-3-yl)-imidazolidin-2-one

수율 52.0%

용매

ethyl acetate

1,4-dioxane

hexane

반응 조건

후처리

1. 1
   기타previously degassed with argon (10 minutes)
2. 2
   기타The reaction was purged with argon for a further 10 minutes
3. 3
   온도the resulting mixture was heated
4. 4
   여과The reaction mixture was filtered through celite
5. 5
   세척the bed was washed with chloroform
6. 6
   기타The organic layer was dried over Na2O4
7. 7
   농축concentrated
8. 8
   기타Purification by column chromatography (using silica gel of mesh size of 60-120, 30% EtOAc in hexane as eluant)

실험 절차

Copper iodide (12.6 mg, 0.066 mmol), trans-1,2-diamino cyclohexane (22.79 mg, 0.199 mmol) and potassium carbonate (183.5 mg, 1.32 mmol) were added to 1,4-dioxane (5 mL) and 3-bromo-5-trifluoromethyl-pyridine (150 mg, 0.66 mmol) previously degassed with argon (10 minutes). The reaction was purged with argon for a further 10 minutes, followed by the addition of 1-naphthalen-2-yl-imidazolidin-2-one (I-79b: 140 mg, 0.66 mmol) and the resulting mixture was heated to reflux at 110° C. for 15 hours. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mixture was filtered through celite and the bed was washed with chloroform. The organic layer was dried over Na2O4 and concentrated. Purification by column chromatography (using silica gel of mesh size of 60-120, 30% EtOAc in hexane as eluant) afforded 120 mg (52% yield) of 1-naphthalen-2-yl-3-(5-trifluoromethyl-pyridin-3-yl)-imidazolidin-2-one.

출처