Water → HCID 86657123, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromonaphthalene-2-carbonitrile (0.57 g) in N,N-dimethylformamide (4 mL) and 4 mol/L HCl 1,4-dioxane solution (4 mL) was added thioacetamide (1.1 g) at room temperature, and the reaction mixture was stirred at 70° C. overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography on silica gel to give 4-bromonaphthalene-2-carbothioamide (0.48 g). To a suspension of this compound (0.48 g) in ethanol (6 mL) was added ethyl 2-chloro-acetoacetate (0.59 g), and the mixture was stirred at 65° C. for 24 hours. After cooling to room temperature, the precipitated solid was collected by filtration, washed with ethanol, and dried to give the title compound (0.41 g).

Provenance & Evidence