4-Nitrobenzoyl chloride → N-[2,6-Dichloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-4-nitro-benzamide

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Reaction Steps

4-Nitrobenzoyl chloride (4.55 g) was dissolved in a pyridine (30 ml) solution of 2,6-dichloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)aniline (2.7 g). The solution was refluxed under heating for 3 hours. After cooling to room temperature, the solution was diluted with water and extracted twice with ethyl acetate. The organic phases were combined and dried over magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off under reduced pressure. The residue was dissolved in tetrahydrofuran (30 ml), and an aqueous solution (5 ml) containing sodium hydroxide (2.0 g) was added, and then stirred at room temperature for 4 hours. The reaction solution was extracted twice with ethyl acetate. The organic phases were combined, washed with 1 N hydrochloric acid and water, and dried over anhydrous magnesium sulfate. The drying agent (i.e., anhydrous magnesium sulfate) was removed by filtration, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography to obtain N-[2,6-dichloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-4-nitrobenzamide (3.27 g, yield 83.4%).

Provenance & Evidence