7377-26-6

62-53-3

3814-10-6

To a 1 L three-necked round-bottomed flask equipped with a magnetic stirrer, a constant-pressure dropping funnel, an ice-water bath, a nitrogen protection system, a condenser tube, and a heating plate, 93.13 g of aniline, 42.30 g of sodium bicarbonate, 0.5 g of triethylamine, and 300 mL of tetrahydrofuran (THF) were added sequentially. The reaction mixture was cooled to below 10°C, followed by the slow dropwise addition of 100 g of methyl 4-chlorocarbonylbenzoate dissolved in 100 mL of THF. The reaction temperature was maintained at about 10°C during the dropwise addition.After the dropwise addition was completed, the reaction mixture was heated to reflux and the progress of the reaction was monitored by infrared spectroscopy (IR) (disappearance of the characteristic peak at 1780 cm-1 indicated completion of the reaction). After completion of the reaction, the reaction solution was diluted to 2 L with cold deionized water and stirring was continued for about 20 min. The solid product was collected by filtration and dried in an oven at 110°C. A final product of 105.6 g of the target product 4-methoxycarbonylbenzanilide was obtained in 82.2% yield.