반응 #9523

반응 방정식

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

수율 95.6%

용매

DMF

반응 조건

후처리

1. 1
   기타The DMF was removed under reduced pressure
2. 2
   기타the 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
   농축The resulting solution was concentrated under reduced pressure
6. 6
   기타to provide a solid
7. 7
   농축The aqueous layer was concentrated under reduced pressure
8. 8
   기타the resulting solid was triturated with methanol
9. 9
   기타isolated by filtration
10. 10
    농축The filtrate was concentrated under reduced pressure
11. 11
    기타the residue was triturated
12. 12
    기타isolated
13. 13
    기타dried under high vacuum

실험 절차

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.

출처