Réaction #9523

Équation de réaction

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

Rendement 95.6%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   AutreThe DMF was removed under reduced pressure
2. 2
   Autrethe 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
   ConcentrationThe resulting solution was concentrated under reduced pressure
6. 6
   Autreto provide a solid
7. 7
   ConcentrationThe aqueous layer was concentrated under reduced pressure
8. 8
   Autrethe resulting solid was triturated with methanol
9. 9
   Autreisolated by filtration
10. 10
    ConcentrationThe filtrate was concentrated under reduced pressure
11. 11
    Autrethe residue was triturated
12. 12
    Autreisolated
13. 13
    Autredried under high vacuum

Mode opératoire

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.

Source