Isopropanol → HCID 178457552, compound

Participants

Reaction Steps

A stirred mixture of N-(3-pyridyl)-N'-cyano-O-phenylisourea (see, Example 5 for procedure) (13.93 g, 0.05836 mol), 1-phenylpropylamine (8.68 g, 0.0642 mol), N-methylmorpholine (139 mL) and isopropanol (92.9 mL) was refluxed, under nitrogen, for 18 hours. The reaction was complete by TLC with 10% MeOH-1% NH4OH-CHCl3. Concentration of the reaction mixture gave a residue that was mixed with EtOAc and concentrated several times until the product crystallized. The solid was boiled twice with small portions of EtOAc; each time the mixture was cooled and the liquid decanted. The resulting solid was crystallized from MeOH-EtOAc to give 7.87 g (43.8%) of product: mp 155°-156° C.

Provenance & Evidence