Methanol → Methyl 3-amino-4-cyano-5-(methylsulfanyl)thiophene-2-carboxylate

Participants

Reaction Steps

A mixture of [bis(methylsulfanyl)methylene]malononitrile (40 g, 230 mmol), methylthioglycolate (21 mL, 230 mmol) and TEA (24 mL, 173 mmol) in MeOH (600 mL) was allowed to stir at reflux for 2 h. The reaction mixture was allowed to cool overnight and the precipitate was filtered off, washed with cold MeOH (×3) to give methyl 3-amino-4-cyano-5-(methylsulfanyl)thiophene-2-carboxylate (52.4 g, 99%). LCMS: (AA) ES+ 229.2. 1H NMR (400 MHz, d6-DMSO) δ: 3.74 s, 3H) and 2.70 (s, 3H).

Provenance & Evidence