Guanidine Hydrochloride → HCID 135546394, compound

Participants

Reaction Steps

Sodium (3.4 g, 147 mmol) was dissolved in ethanol (500 ml), and then 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 cooling as it was, the solvent was removed. Tetrahydrofuran (500 ml) was added to the residue, the insoluble matters were filtered off, and the filtrate was concentrated. To a solution of the residue in tetrahydrofuran (1500 ml)-methanol (100 ml) was added active manganese dioxide (250 g), followed by heating under reflux. After 2 hours, additional active manganese dioxide (100 g) was added thereto, followed by heating under reflux further for 1 hour and 15 minutes. After cooling as it was, the manganese dioxide was filtered off through Celite and washed with tetrahydrofuran and methanol. The collected filtrate was concentrated and acetonitrile was added to the residue. The resulting precipitates were collected by filtration, to give the title compound (15 g, 44%) as a yellow powder.

Provenance & Evidence