Sodium Bicarbonate → 3-(1-cyano-1-methylethyl)-N-(4-ethyl-3-hydroxyphenyl)benzamide

Participants

Reaction Steps

To a two-layer solution of 5-amino-2-ethylphenol hydrochloride (2.2 g, 12.6 mmol) in tetrahydrofuran (20 mL)/1N aqueous sodium hydrogen carbonate solution (38 mL) was added a solution of 3-(1-cyano-1-methylethyl)benzoyl chloride synthesized above in tetrahydrofuran (20 mL), and the mixture was stirred at room temperature for 12 hr. The aqueous layer was separated, and extracted with ethyl acetate (80 mL). The combined organic layer was washed with water (40 mL) and saturated brine (40 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. Ethyl acetate (45 mL)/hexane (25 mL) was added to the obtained residue, and the obtained solid was collected by filtration to give the title compound (3.48 g, 90%) as a colorless powder.

Provenance & Evidence