Potassium Iodide → 4-{[({(1-methyl-1H-tetrazol-5-yl)[3-(trifluoromethoxy)phenyl]methylene}amino)oxy]methyl}-1,3-thiazol-2-amine

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To a stirred solution of N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-[3-(trifluoromethoxy)phenyl]methanimine (220 mg, 0.73 mmol) in acetonitrile (10 mL) were added cesium carbonate (498 mg, 1.53 mmol), potassium iodide (60 mg, 0.36 mmol) and 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (156 mg, 0.80 mmol). After stirring for 18 h at room temperature, the mixture was filtered, the filtrate concentrated in vacuo. Purification of the residue on silica gel afforded 4-{[({(1-methyl-1H-tetrazol-5-yl)[3-(trifluoromethoxy)phenyl]methylene}amino)oxy]methyl}-1,3-thiazol-2-amine as an oil [230 mg, yield 79%; HPLC/MS:m/z=400 (M+H); log P(HCOOH)=2.10].

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