1,4-Dioxane → N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-1-methyl-3-(pentafluoroethyl)-4-iodo-1H-pyrazole-5-carboxamide

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Reaction Steps

0.49 g (2.34 mmol) of 4-chloro-3-(cyclopropylcarbamoyl)aniline dissolved in 0.5 ml of dioxane are added dropwise to a solution of 1.28 g (2.34 mmol) of 4-iodo-1-methyl-3-pentafluoroethyl-1H-pyrazolecarboxylic acid and 0.54 g (2.81 mmol) of 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride in 20 ml of dioxane and the reaction mixture is stirred for three days at room temperature. The majority of the dioxane is distilled off at reduced pressure on a rotary evaporator and the residue is admixed with 20 ml of water. The aqueous phase is extracted three times with ethyl acetate and the organic phase is then washed three times with saturated sodium chloride solution. After drying over sodium sulphate, the solvent is distilled off at reduced pressure on a rotary evaporator and the residue is purified by means of flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate). This gives 0.70 g of N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-1-methyl-3-(pentafluoroethyl)-4-iodo-1H-pyrazole-5-carboxamide (53%) as an oil.

Provenance & Evidence