Acetonitrile → HCID 21866489, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 20.5 g (97.5 mmol) of ethyl 2-amino-3-cyano-4-methylthiophene-5-carboxylate in 600 ml of a 1:1 mixture of acetonitrile and dimethylformamide was cooled to 5° C., and 15.7 g (146 mmol) of tert-butyl nitrite were added dropwise, during which process the temperature of the reaction mixture rose and gas was evolved vigorously. The mixture was stirred for seven hours at room temperature and concentrated on a rotary evaporator under a high vacuum, the residue was purified by column chromatography (eluant dichloromethane), and 9.1 g (48%) of the desired compound were obtained as yellow oil. 1H NMR (270 MHz, DMSO-d6): δ=1.3 (t, 3H), 2.55 (s, 3H), 4.3 (q, 2H), 8.8 (s, 1H).

Provenance & Evidence