반응 #46682

반응 방정식

sodium hydrogencarbonate

2-(1-adamantyl)-N-pentylethylamine hydrochloride

4-(3-aminopropyl)pyridine

1,1′-thiocarbonyldiimidazole

→

compound

수율 24.0%

1-[2-(1-Adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)propyl]thiourea

수율 24.0%

용매

ethyl acetate

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   온도the whole was refluxed for 2.5 hours
2. 2
   기타After separation
3. 3
   세척the ethyl acetate layer was washed with a saturated aqueous sodium chloride solution (50 ml)
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   농축concentrated under reduced pressure
6. 6
   농축Then the obtained concentrate
7. 7
   기타was purified by silica gel column chromatography

실험 절차

A solution of 4-(3-aminopropyl)pyridine (Intermediate No. 2-1, 0.24 g, 1.8 mmol) in anhydrous tetrahydrofuran (10 ml) was added to 1,1′-thiocarbonyldiimidazole (0.31 g, 1.8 mmol) under a nitrogen atmosphere, and the mixture was stirred at room temperature. After one hour, a solution of 2-(1-adamantyl)-N-pentylethylamine hydrochloride (Intermediate No. 1-1, 0.50 g, 1.8 mmol) in anhydrous tetrahydrofuran (10 ml) was added to the mixture, and the whole was refluxed for 2.5 hours. The reaction mixture was allowed to stand, and then ethyl acetate (50 ml) and a saturated aqueous sodium hydrogencarbonate solution (50 ml) were added to the reaction mixture. After separation, the ethyl acetate layer was washed with a saturated aqueous sodium chloride solution (50 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Then the obtained concentrate was purified by silica gel column chromatography to give the target compound (0.18 g, 24%).

출처