Dimethylformamide → 2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}-N-(5-methoxy-2-nitrophenyl)-N-methylacetamide

Participants

Reaction Conditions

Reaction Steps

To a suspended solution of 4-[(2,4-dioxothiazolidin-5-yl)methyl]phenoxyacetic acid (8.00 g) in acetonitrile (64 ml) were added thionyl chloride (3.38 g) and dimethylformamide (3.2 ml) at room temperature, and the resulting mixture was stirred successively at 25° C. for 30 minutes and at 40° C. for 30 minutes. Subsequently, to the reaction mixture were added successively N-(5-methoxy-2-nitrophenyl)-N-methylamine (3.84 g), N,N-dimethylaminopyridine (0.32 g) and acetonitrile (16 ml), and the resulting mixture was stirred at the same temperature for 1 hour. After cooling the reaction mixture to 0° C., water (32 ml) was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate (80 ml). The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate twice (16 ml for each) and evaporated to dryness to afford the title compound (9.67 g, yield: 100%) as an orange-colored amorphous solid.

Provenance & Evidence