Reaktion #9523

Reaktionsgleichung

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

Ausbeute 95.6%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe DMF was removed under reduced pressure
2. 2
   Sonstigethe 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
   EinengenThe resulting solution was concentrated under reduced pressure
6. 6
   Sonstigeto provide a solid
7. 7
   EinengenThe aqueous layer was concentrated under reduced pressure
8. 8
   Sonstigethe resulting solid was triturated with methanol
9. 9
   Sonstigeisolated by filtration
10. 10
    EinengenThe filtrate was concentrated under reduced pressure
11. 11
    Sonstigethe residue was triturated
12. 12
    Sonstigeisolated
13. 13
    Sonstigedried under high vacuum

Vorschrift

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.

Quelle