Propyl isocyanate → 2,4-dihydro-5-methyl-2-(4-nitrophenyl)-4-propyl-3H-1,2,4-triazol-3-one

Participants

Reaction Steps

A mixture of 13 parts of 1-[1-(4-morpholinyl)ethylidene-2-(4-nitrophenyl)hydrazine, 8.5 parts of 1-isocyanatopropane, 1 part of N,N-dimethyl-4-pyridinamine and 39 parts of dichloromethane was stirred and refluxed for 2 hours. The whole was evaporated and 90 parts of dimethylbenzene were added to the residue. Stirring at reflux was continued for 3 hours. The reaction mixture was cooled and filtered over diatomaceous earth. The filtrate was saturated with petroleum ether. The precipitated product was filtered off and crystallized from 2-propanol, yielding 8.5 parts (65%) of 2,4-dihydro-5-methyl-2-(4-nitrophenyl)-4-propyl-3H-1,2,4-triazol-3-one; mp. 125.4° C. (int. 20).

Provenance & Evidence