Cyanamide → HCID 86624873, compound

Participants

Reaction Steps

To a solution of dihydro-2H-pyran-3(4H)-one (purchased from JW-Pharmlab) (5.0 g, 50 mmol) in cyclohexane (100 mL) were added pyrrolidine (4.3 mL, 52 mmol) and p-toluenesulfonic acid monohydrate (0.05 g). The reaction mixture was refluxed for 3 h with a Dean-Stark trap, cooled and concentrated. The residue was dissolved in methanol (80 mL) and then sulfur (1.66 g, 52 mmol) was added. To the mixture was added a solution of cyanamide (2.52 g, 52 mmol) in methanol (20 mL) at 0° C. The reaction mixture was stirred at room temperature overnight, filtered, concentrated and purified by column chromatography using an Analogix® IT280™ (SiO2, 0-5% methanol in dichloromethane) to afford 0.4 g (5%) of the title compound. MS (ESI+) m/z 157 (M+H)+.

Provenance & Evidence