Process for preparation of 4-aryl-1,2,4-triazol-3-ones

Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...

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5482636, 5482646, C07D40310, C07D24912

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active

057288348

ABSTRACT:
A process for preparing 4-aryl-1,2,4-triazol-3-ones and 4-aryl-5-alkoxy-1,2,4-triazol-3-ones. A reaction mixture includes a primary aromatic amine, an alkyl carbazate and a trialkyl orthoformate. The reactants are heated in a reaction vessel in the presence of an acid catalyst and a polar solvent. After the reaction is complete, the solvent is removed, water is added, and the slurry is filtered to isolate 4-aryl-5-alkoxy-1,2,4-triazol-3-one. Alternatively, after the reaction is complete, an alkali metal alkoxide is added to the reaction mixture in the vessel, and the new mixture is again heated until the reaction is complete. The solvent is distilled from the mixture, and the remaining mixture is diluted with water. The slurry is separated from mixture, washed and dried to obtain 4-aryl-1,2,4-triazol-3-one in near 100% yield.

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