Triethylamine → 2-(Trifluoromethylsulfonamido)ethyl methacrylate

Participants

Reaction Conditions

Reaction Steps

In a 1 L three-neck flask equipped with a thermometer and a reflux condenser were placed 350 g of acetonitrile, 70.7 g (0.699 mol) of triethylamine, 33.1 g (0.200 mol) of 2-aminoethyl 2-methylacrylate hydrochloride, and 0.2 g of phenothiazine, followed by cooling to −30° C. with stirring. After the inner temperature reached −30° C., 40.3 g (0.239 mol) of trifluoromethanesulfonyl chloride was introduced into the slurry as a gas over a period of 1 hour. After completion of the introduction, the mixture was continued to stir for further 1 hour and then warmed to room temperature. The solvent acetonitrile and unreacted trifluoromethanesulfonyl chloride were removed by evaporation from the reaction solution under reduced pressure. One litter of diisopropyl ether was added thereto to form a suspension and the precipitated triethylamine hydrochloride was removed by filtration. The filtrate was washed with 200 mg of a 10% aqueous sodium chloride solution three times. The organic layer was dried over 40 g of magnesium sulfate. After removal of the magnesium sulfate by filtration, 0.2 g of phenothiazine was added thereto and the solvent was removed by evaporation to obtain 22.5 g of a crude organic matter. The crude organic matter was distilled under reduced pressure and a fraction of 105 to 115° C./13 Pa was collected, whereby 9.9 g of 2-{[(trifluoromethyl)sulfonyl]amino}ethyl 2-methylacrylate was obtained. Gas chromatographic investigation of composition thereof revealed that objective 2-{[(trifluoromethyl)sulfonyl]amino}ethyl 2-methylacrylate was 98.0%. The yield was 18.6%.

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