تفاعل #46682

معادلة التفاعل

sodium hydrogencarbonate

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

4-(3-aminopropyl)pyridine

1,1′-thiocarbonyldiimidazole

→

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
   أخرىAfter separation
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
   تركيزconcentrated under reduced pressure
6. 6
   تركيزThen the obtained concentrate
7. 7
   أخرىwas 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, 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%).

المصدر