Water → HCID 67308893, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromonaphthalene-2-carboxylic amide (1.10 g) in toluene (11.0 mL) was added chlorocarbonylsulfenyl chloride (0.73 mL), and the mixture was stirred at 100° C. for 18 hours. To the reaction solution was added water (50 mL). The precipitated solid was collected by filtration, and washed with water and hexane to give 5-(4-bromonaphthalene-2-yl)-[1,3,4]oxathiazole-2-one (1.13 g). This compound (1.12 g) was dissolved in dichlorobenzene (18 mL). To the solution was added ethyl cyanoformate (1.42 mL), and the mixture was stirred at 160° C. for 22 hours. To the mixture was added water (30 mL) at room temperature, and the resulting mixture was extracted with dichloromethane. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate) to give the title compound (1.21 g).

Provenance & Evidence