1-[2-(4-nitrophenoxy)ethyl]-1,2,4-triazole → HCID 4295342, compound

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Reaction Steps

2-(4-nitrophenoxy) ethanol (3.0 g) was dissolved in THF (60 ml), triethylamine (2.74 ml) and methanesulfonyl chloride (1.4 ml) were added to the mixture, and the mixture was stirred for 1 hour at room temperature. The reaction solution was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and a solution (15 ml) of the obtained residue in DMF was added dropwise to a solution (30 ml) of 1,2,4-triazole (1.0 g) and potassium carbonate (3.4 g) in DMF. The mixture was stirred for 16 hours at 90° C., and cooled to room temperature. The reaction solution was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give 1-[2-(4-nitrophenoxy)ethyl]-1,2,4-triazole (1.7 g). To 1-[2-(4-nitrophenoxy)ethyl]-1,2,4-triazole (1.6 g) was added 85% ethanol solution (48 ml), calcium chloride (0.38 g) and reduced iron (1.91 g) were added to the mixture, and the mixture was heated to reflux for 3 hours. After cooling to room temperature, the mixture was filtered with Celite, and washed with ethyl acetate. The solvent was removed under reduced pressure, and the obtained residue was dissolved in ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 4-[2-(1,2,4-triazol-1-yl)ethoxy]aniline (0.92 g).

Provenance & Evidence