Aniline → Ethyl 3-anilino-2-cyano-3-methylsulfanylprop-2-enoate

Participants

Reaction Steps

A solution of ethyl 3,3-bis(methylthio)-2-cyanoacrylate (20.0 g, 91.2 mmol) and aniline (9.1 mL, 100 mmol) in ethanol (200 mL) was heated under reflux for 16 hr. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluate, hexane:ethyl acetate=98:2→1:1) to give the title compound (21.0 g, 88%) as a white powder.

Provenance & Evidence