反応 #11564

反応方程式

sodium hydrogencarbonate

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

4-(3-aminopropyl)pyridine

1,1′-thiocarbonyldiimidazole

→

titled compound

収率 24.0%

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

収率 24.0%

溶媒

ethyl acetate

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   温度the whole was refluxed for 2.5 hours
2. 2
   その他were separated
3. 3
   洗浄The ethyl acetate layer was washed with a saturated aqueous sodium chloride solution (50 ml)
4. 4
   乾燥dried over anhydrous magnesium sulfate
5. 5
   濃縮The ethyl acetate layer was concentrated under reduced pressure
6. 6
   その他the concentrate was purified by silica gel column chromatography

実験手順

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, then ethyl acetate (50 ml) and a saturated aqueous sodium hydrogencarbonate solution (50 ml) were added to the reaction mixture, and layers were separated. The ethyl acetate layer was washed with a saturated aqueous sodium chloride solution (50 ml) and dried over anhydrous magnesium sulfate. The ethyl acetate layer was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography to give 0.18 g (24%) of the titled compound.

出典