Sodium Iodide → N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (2.54 g, 12.5 mmol) in acetonitrile (75 mL), were added cesium carbonate (8.55 g, 26.2 mmol), sodium iodide (187 mg, 1.25 mmol) and 2-Bromo-4-bromomethyl-thiazole (3.53 g, 13.7 mmol). The resulting suspension was stirred at 25° C. for 30 minutes, then at 40° C. for 90 minutes. After cooling, the suspension was diluted with ethyl acetate (80 mL), filtered over a plug of celite, the solvents were evaporated in vacuo. Purification on silica gel afforded N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenyl-methanimine as an oil that solidified on standing after 2 days (4.19 g, yield 88%).

Provenance & Evidence