反应详情

温度

60 °C

A round bottom flask was charged with a magnetic stir bar, N,N-dibenzyl-1-(4-chlorobutyl)-1H-imidazo[4,5-c]quinolin-4-amine (7.0 g, 15.38 mmol), sodium benzenethiolate (3.46 g, 26.15 mmol), and anhydrous dimethyl formamide (77 mL) under a nitrogen atmosphere. The reaction mixture was heated to 60° C. to give a heterogeneous mixture that was maintained at 60° C. for 4 hours at which time the starting material was completely consumed. The cooled solution was partitioned between ethyl acetate and water. The layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to afford a colorless oil. The material was purified by chromatography over silica gel (80/20 hexanes/ethyl acetate) to provide N,N-dibenzyl-1-[4-(phenylthio)butyl]-1H-imidazo[4,5-c]quinolin-4-amine (7.5 g, 14.19 mmol) as a colorless oil. MS (CI) for C34H32N4S m/z 529 (MH+), 439, 349.

1. additionA round bottom flask was charged with a magnetic stir bar
2. customto give a heterogeneous mixture that
3. temperaturewas maintained at 60° C. for 4 hours at which time the starting material
4. customwas completely consumed
5. customThe cooled solution was partitioned between ethyl acetate and water
6. customThe layers were separated
7. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customto afford a colorless oil
12. customThe material was purified by chromatography over silica gel (80/20 hexanes/ethyl acetate)