Acetonitrile → HCID 53482827, compound

Participants

Reaction Steps

To a flame-dried 25 mL round-bottom flask equipped with a magnetic stirring bar was added m-toluidine (365 mg, 3.4 mmol), o-tolualdehyde (391 mg, 3.3 mmol) and 5 mL of dry acetonitrile. The solution was stirred to make a homogeneous solution, then trimethylsilyl cyanide (480 μL, 3.6 mmol) was added and the solution stirred at room temperature for 23 h. The reaction was quenched by adding 5.5 mL satureated ammonium chloride solution and allowed to vent. The reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and concentrated to give the crude product (50% dichloromethane/hexanes, Rf=0.025). The crude was dissolved in a minimal amount of boiling toluene, a 4-5 fold volume of hexanes added and the solution allowed to sit for several hours, filtered, and dried to give XXX (531 mg, 68.1% yield) as a crystalline solid. Approximately 400 mg of the recrystallized material was additionally purified by flash chromatography using 50% dichloromethane/hexanes, which, after concentration, gave XXX as a white crystalline solid (m.p. 103-104° C.).

Provenance & Evidence