(2,4,6-Trichlorophenyl)hydrazine → 5-Cyano-6-methyl-1-(2,4,6-trichloroanilino)-2,4-pyrimidinedione
Reaktionsgleichung
ClC1C=C(Cl)C=C(Cl)C=1NN.[C:12]([C:14](=[C:23]([CH3:35])[NH:24][NH:25][C:26]1[C:31]([Cl:32])=[CH:30][C:29]([Cl:33])=[CH:28][C:27]=1[Cl:34])[C:15]([NH:17][C:18](OCC)=[O:19])=[O:16])#[N:13]>>[C:12]([C:14]1[C:15](=[O:16])[NH:17][C:18](=[O:19])[N:24]([NH:25][C:26]2[C:31]([Cl:32])=[CH:30][C:29]([Cl:33])=[CH:28][C:27]=2[Cl:34])[C:23]=1[CH3:35])#[N:13]Komponenten
3
Versuchsvorschrift
Following the method of Example 1, N-ethoxycarbonylcyanoacetamide is heated with triethyl orthoacetate and acetic anhydride to give α-cyano-β-ethoxy-β-methyl-N-ethoxycarbonylacrylamide, which in turn is reacted with 2,4,6-trichlorophenylhydrazine. The resulting compound α-cyano-β-methyl-β-(2,4,6-trichlorophenylhydrazino)-N-ethoxycarbonylacrylamide (m.p.=183°-184°) is cyclized, yielding 5-cyano-6-methyl-1-(2,4,6-trichloroanilino)-2,4-pyrimidinedione, m.p.=>305°.