تفاعل #11564

معادلة التفاعل

sodium hydrogencarbonate

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

4-(3-aminopropyl)pyridine

1,1′-thiocarbonyldiimidazole

→

titled compound

المردود 24.0%

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

المردود 24.0%

المذيبات

ethyl acetate

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe whole was refluxed for 2.5 hours
2. 2
   أخرىwere separated
3. 3
   غسيلThe ethyl acetate layer was washed with a saturated aqueous sodium chloride solution (50 ml)
4. 4
   تجفيفdried over anhydrous magnesium sulfate
5. 5
   تركيزThe ethyl acetate layer was concentrated under reduced pressure
6. 6
   أخرىthe concentrate was purified by silica gel column chromatography

الإجراء التجريبي

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.

المصدر