Methyl iodide → HCID 66619915, compound

Participants

Reaction Steps

A suspension of tert-butyl 2,2-dimethyl-3-(2-thioxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)propylcarbamate (7.78 g, 20.1 mmol) and 100 mL of 1:1 water/ethanol was treated with 20 mL of concentrated ammonium hydroxide and iodomethane (1.50 mL, 24.2 mmol). Two hours later an additional 50 mL of H2O was added, and the precipitate was filtered and rinsed with ether. When the ether was added, the funnel became clogged, so the precipitate was transferred into a flask with the aid of methanol and CH2Cl2. The solvents were removed under reduced pressure to give a light yellow solid. The filtrate was then concentrated under reduced pressure to ˜150 mL of mostly water. Organic material was extracted from this solution using CH2Cl2 (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, combined with the precipitated material, and concentrated under reduced pressure to give tert-butyl 2,2-dimethyl-3-[2-(methylthio)-1H-imidazo[4,5-c]quinolin-1-yl]propylcarbamate (7.81 g) as a light yellow solid.

Provenance & Evidence