Ammonia → 4-amino-3-ethyl-1H-1,2,4-triazol-5-one

Participants

Reaction Conditions

Reaction Steps

Analogously to Example 3, a solution of carbodihydrazide in phenol is prepared from 3,200 g (64 mol) of hydrazine hydrate and 6,848 g (32 mol) of diphenyl carbonate and the water of hydration and also 1,500 ml of phenol are then distilled off. After addition of 3 g of dimethyltin oxide and 1,848 g (33.6 mol) of propionitrile, the mixture is heated to a weak reflux (125° C.). The temperature can be increased to 180° C. in the course of 11 hours under a continuous reflux. Thereafter, the evolution of NH3 has ended. Phenol is now distilled off at a bottom temperature of 160° C. under reduced pressure (decreasing to 15 mbar), the residue remaining liquid. Residual phenol is therefore removed under 1 mbar using an oil pump. After cooling, the residue is dissolved in 3 L of hot water. 80 ml of diethylamine and 10 g of tartaric acid (to remove a slight turbidity caused by the catalyst) are added to the solution. A diethylamine excess and traces of phenol are removed by incipient distillation. After cooling to 10° C., the product is filtered off with suction, washed with 500 ml of cold 50% strength ethanol and dried at 100° C. in vacuo. 3,478 g (85% of theory) of 3-ethyl-4-amino-1,2,4-triazol-5-one of melting point 171° C. are obtained.

Provenance & Evidence