Benzyl Chloride → HCID 13958467, compound

Participants

Reaction Steps

To a solution of 4.4 g (0.071 mole) of 1-isobutyl-2-mercapto-1H-imidazo[4,5-c]quinoline (from Example 164, Part B below) in 45 ml of methanol and was added 4.1 g (0.0188) of 25% sodium methoxide in methanol, then 2.4 g (0.0188 mole) of benzyl chloride. The solution was heated at reflux for 0.5 hour, then evaporated. Water was added to the residue, and the mixture was extracted with dichloromethane. The extracts were dried over sodium chloride, and then evaporated. The residue was dissolved in diethyl ether, and the solution was saturated with hydrogen chloride. The precipitate was separated by filtration, washed with ether and recrystallized from a mixture of ethanol and diethyl ether to provide 2-benzylthio-1-isobutyl-1H-imidazo[4,5-c]quinoline hydrochloride, m.p. 205°-207° C. Analysis: Calculated for C21H21N3S.HCl: %C, 65.7; %H, 5.8; %N, 10.9; Found: %C, 65.4; %H, 5.6; %N, 10.9.

Provenance & Evidence