反应 #9523

反应方程式

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

收率 95.6%

溶剂

DMF

反应条件

后处理

1. 1
   其他The DMF was removed under reduced pressure
2. 2
   其他the 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
   浓缩The resulting solution was concentrated under reduced pressure
6. 6
   其他to provide a solid
7. 7
   浓缩The aqueous layer was concentrated under reduced pressure
8. 8
   其他the resulting solid was triturated with methanol
9. 9
   其他isolated by filtration
10. 10
    浓缩The filtrate was concentrated under reduced pressure
11. 11
    其他the residue was triturated
12. 12
    其他isolated
13. 13
    其他dried under high vacuum

实验过程

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.

来源