Water → N-[2-(4-chlorophenoxy)-1-(4-fluorophenyl)ethylidene]-1H-1,2,4-triazol-1-amine

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Reaction Steps

To a stirred solution of 1-amino-1H-1,2,4-triazole (75% purity, 5.6 g, 0.05 mmol) and 2-(4-chlorophenoxy)-4'-fluoroacetophenone (13.2 g, 0.05 mmol) in 100 mL dry toluene is added a catalytic amount (1.0 g) p-toluene sulfonic acid. The mixture is heated at reflux with azeotropic removal of water for 4 days. Solvent is evaporated and the residue taken up in 200 mL ethyl acetate. The organic solution is washed with 2×100 mL 10% aqueous Na2CO3 and 1×100 mL brine. The dried (MgSO4) solution is filtered and concentrated to give the desired product which can be purified by chromatography or crystallization from an appropriate solvent.

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