Methanol → HCID 178515389, compound

Participants

Reaction Steps

To a stirred solution of cyclopentanone (24 mmol) and malononitrile (24 mmol) in 7.5 mL of MeOH and 1.5 mL of DMF was added 5 mL carbon disulfide followed by the slow addition of 1.5 mL of Et3N. Upon completion of addition, the resulting solution was stirred at RT for 36 h. After this time, the resulting red precipitate was collected by filtration and washed with MeOH. The red solid filter cake was taken up in 50 mL of 1N NaOH. The resulting mixture was stirred at 150° C. for 7 h and then cooled to RT. Once at the prescribed temperature, the resulting red solution was acidified with 6 N HCl. The resulting yellow precipitate was collected by filtration, washed with water and then dried in vacuum to provide the title compound as a red solid (0.35 g, 16%). LC/MS m/z 168 (M+H).

Provenance & Evidence