Acetophenone → 4-(4-bromophenyl)-2,6-diphenylpyrimidine

Participants

Reaction Steps

Into a 300-mL three-neck flask were put 11 mL (94.6 mmol) of acetophenone and 17.9 g (96.7 mmol) of 4-bromobenzaldehyde, and the air in the flask was replaced with nitrogen. To this mixture, 50 mL of ethanol was added and 5.99 g (110.9 mmol) of sodium methoxide suspended in 50 mL of ethanol was added dropwise. The mixture was stirred at room temperature for 5 hours and further stirred at 70° C. for 50 minutes. After the predetermined time elapsed, 15.1 g (96.6 mmol) of benzamidine hydrochloride and 8.03 g (200 mmol) of sodium hydroxide were added and the mixture was stirred at 70° C. for 9 hours. After the predetermined time elapsed, this mixture was suction-filtered, and the obtained residue was dissolved in chloroform and subjected to extraction with water. The obtained organic layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. This mixture was subjected to gravity filtration, and the solvent was distilled off to give a solid. The obtained solid was washed with ethanol, so that 8.61 g of an objective white solid was obtained in a yield of 22%.

Provenance & Evidence