Acetone → HCID 15512739, compound

Participants

Reaction Steps

3,5-dihydroxybenzonitrile (0.50 g), 1-bromopentadecane (2.70 g), potassium carbonate (2.56 g), and 30 ml of acetone were mixed and the mixture was heated overnight under reflux. After water was added, the mixture was extracted with methylene chloride. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed by evaporation to obtain 0.33 g of 3,5-dipentadecyloxybenzonitrile as colorless crystals. This product was dissolved in a mixed solvent of 20 ml of methanol and 35 ml of benzene and hydrogen chloride gas was allowed to flow into the mixture for 1 hour under ice-cooling. The solvent was removed by evaporation under reduced pressure and the thus-obtained crystals were recrystallized from chloroform and hexane to obtain 0.28 g of 3,5-dipentadecyloxy-α-methoxy-α-iminotoluene hydrochloride. This product was dissolved in 10 ml of chloroform, ammonia gas was allowed to flow into the solution for 40 minutes under ice-cooling, then the mixture was heated for 4.5 hours under reflux. After the solvent was removed by evaporation under reduced pressure, the materials insoluble in chloroform were removed from the resulting solid to obtain 0.20 g of 3,5-dipentadecyloxybenzamidine as colorless crystals. The data obtained by instrumental analysis of this compound support the structure represented by the following formula 3.

Provenance & Evidence