N-(3-cyanophenyl)benzamide

Synthesis

93-58-3

2237-30-1

141990-91-2

GENERAL PROCEDURE: Pure m-aminobenzonitrile (1.00 mmol) and methyl benzoate (1.00 mmol) with DABAL-Me3 (202 mg, 0.8 eq.) are placed in a 5 mL microwaveable vial and dry tetrahydrofuran (1 mL) is added under argon protection. For coupled spouses containing acidic hydrogen, additional DABAL-Me3 (410 mg, 1.6 eq. total) is added. The vials were quickly capped and placed in a CEM Discover microwave reactor. Irradiation was carried out at 130 °C for 8 min at 290 W power, followed by programmed cooling (~20 min). The reaction was quenched by careful addition of 2 M hydrochloric acid (4 mL) or saturated potassium sodium tartrate solution (4 mL) (note: methane may be released). The reaction mixture is extracted with dichloromethane, dried over magnesium sulfate and concentrated to give pure N-(3-cyanophenyl)benzamide directly. For further purification, the amides lacking highly polar functional groups can be separated by column chromatography using 3:2 to 2:3 hexane:ethyl acetate as eluent; for amides containing polar functional groups such as side-chain amines, alcohols, etc., dichloromethane containing 2% v/v methanol is used as eluent.

References