Phenylurea → 4-Phenylsemicarbazide
Reaction equation
[NH2:1]N.[C:3]1([NH:9][C:10]([NH2:12])=[O:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>>[C:3]1([NH:9][C:10](=[O:11])[NH:12][NH2:1])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1Participants
3
Reactant 2
Product 1
Procedure
Other known methods for the preparation of 4-aryl-1,2,4-triazol-3-ones involve the use of hydrazine as a raw material. In one such method, phenylurea is reacted with hydrazine to give a 4-phenylsemicarbazide. The semicarbazide is then condensed with ethyl formate to give the 4-phenyltriazolone. The overall yield from this method is about 20%. In another method, a 4-phenylsemicarbazide is reacted with formic acid to form the 1-formyl-4-phenylsemicarbazide intermediate, followed by intramolecular condensation to the 4-phenyltriazolone. The yield obtained by this method is about 40%. In yet another method, a substituted aniline is converted to the phenylcarbamate derivative. The phenylcarbamate is treated with hydrazine to give the phenylsemicarbazide derivative, followed by condensation with formamidine acetate to give the 4-phenyltriazolone. Each of these methods requires the use of the toxic compound hydrazine. In addition, the methods suffer from low overall yield.