Guanidine Hydrochloride → HCID 135546394, compound

Participants

Reaction Steps

Sodium (3.4 g, 147 mmol) was dissolved in ethanol (500 mL), and ethyl (E)-3-(3-fluorophenyl)-2-(4-pyridyl)-2-propenoate (33 g, 121 mmol) and guanidine hydrochloride (13.9 g, 146 mmol) were added thereto, followed by heating under reflux for 13 hours. After standing to cool, the solvent was removed and to the residue was added tetrahydrofuran (500 mL). The insoluble matters were filtered off, and the filtrate was concentrated. To a solution of the residue in tetrahydrofuran (1500 mL) and methanol (100 mL) was added activated manganese dioxide (250 g), followed by heating under reflux. After 2 hours, additional activated manganese dioxide (100 g) was added and the mixture was heated under reflux further for one and a quarter hour. After standing to cool, manganese dioxide was filtered off through Celite, and washed with tetrahydrofuran and methanol. The combined filtrates were concentrated, and to the residue was added acetonitrile. The resulting precipitates were collected by filtration, to give the title compound (15 g, 44%) as a yellow powder.

Provenance & Evidence