Hydrochloric Acid → HCID 58175669, compound

Participants

Reaction Steps

A mixture of N-(3,5-diisobutylbiphenyl-4-yl)benzamide (6.27 g, 16.3 mmol), phosphorus oxychloride (20 mL), and phosphorus pentachloride (3.40 g, 16.3 mmol) was stirred at reflux for 4 h. The phosphorus oxychloride was removed by vacuum distillation. To the crude imidoyl chloride was added isopropanol (40 mL) and aminoacetaldehyde dimethyl acetal (35 mL, 321 mmol). This was stirred at ambient temperature for 18 h after which time conc. HCl (75 mL) was added. This was stirred at reflux for 18 h. The mixture was neutralized with 1N NaOH to pH 9 and extracted with dichloromethane. The product was purified on a silica gel column. Elution first with dichloromethane then dichloromethane and ethyl acetate (9:1) gave the desired product which was recrystallized from hexane to give 3.64 g (55% yield) as a white solid. Structure was confirmed by LC-MS and 1H NMR.

Provenance & Evidence