Реакция #9523

Уравнение реакции

Thiourea

potassium iodide

7-bromo-1-(5-chloropentyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline

→

2-[5-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentyl]isothiourea hydrochloride

Выход 95.6%

Растворители

DMF

Условия реакции

Обработка

1. 1
   ДругоеThe DMF was removed under reduced pressure
2. 2
   Другоеthe residue was partitioned between saturated aqueous sodium bicarbonate (40 mL) and dichloromethane (50 mL)
3. 3
   workup.ADDITIONThe mixture was adjusted to pH 7 with the addition of 10% hydrochloric acid
4. 4
   workup.DISSOLUTIONwas dissolved with methanol
5. 5
   КонцентрированиеThe resulting solution was concentrated under reduced pressure
6. 6
   Другоеto provide a solid
7. 7
   КонцентрированиеThe aqueous layer was concentrated under reduced pressure
8. 8
   Другоеthe resulting solid was triturated with methanol
9. 9
   Другоеisolated by filtration
10. 10
    КонцентрированиеThe filtrate was concentrated under reduced pressure
11. 11
    Другоеthe residue was triturated
12. 12
    Другоеisolated
13. 13
    Другоеdried under high vacuum

Методика

Thiourea (0.29 g, 3.8 mmol) and potassium iodide (0.052 g, 3.1 mmol) were sequentially added to a suspension of 7-bromo-1-(5-chloropentyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline (1.3 g, 3.2 mmol) in DMF (15 mL), and the reaction was heated at 110° C. for 24 hours. The DMF was removed under reduced pressure, and the residue was partitioned between saturated aqueous sodium bicarbonate (40 mL) and dichloromethane (50 mL). The mixture was adjusted to pH 7 with the addition of 10% hydrochloric acid. Product remained on the walls of the reaction flask and was dissolved with methanol. The resulting solution was concentrated under reduced pressure to provide a solid. The aqueous layer was concentrated under reduced pressure, and the resulting solid was triturated with methanol and isolated by filtration. The filtrate was concentrated under reduced pressure, and the residue was triturated and isolated as described above. The isolated solids were combined and dried under high vacuum to provide 1.49 g of 2-[5-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentyl]isothiourea hydrochloride as a yellow solid.

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