Реакция #6277

Уравнение реакции

water

benzoylene urea

4-(3-chloropropylthio)pyridine

1,8-diazabicyclo[5.4.0]-7-undecene

→

3-[3-(4-pyridylthio)propyl]quinazoline-2,4-(1H,3H)-dione

Выход 31.1%

Растворители

dimethylformamide

Условия реакции

Обработка

1. 1
   ТемператураAfter cooling
2. 2
   Экстракцияthe mixture was extracted with ethyl acetate
3. 3
   ДругоеThe extract was dried
4. 4
   workup.DISTILLATIONthe solvent was distilled off
5. 5
   ДругоеThe residue was purified by column chromatography (eluent: ethyl acetate/ethanol =25:1 to 10:1 to 2:1)

Методика

To a solution of 1.62 g (10 mmol) of benzoylene urea and 1.88 g (10 mmol) of 4-(3-chloropropylthio)pyridine in 50 ml of dimethylformamide, 1.65 ml (11 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, and the mixture was stirred at 80° C. for 16 hours. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried and the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate/ethanol =25:1 to 10:1 to 2:1). First, 0.973 g of 3-[3-(4-pyridylthio)propyl]quinazoline-2,4-(1H,3H)-dione (31.1% yield, pale yellow crystals) was obtained, and then, 0.487 g of the desired product was obtained (10.4% yield, yellow oil).

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