Taurine → 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethanesulfonate potassium

Participants

Reaction Steps

Following the method described by Winterbottom, R. et al., J. Am. Chem. Soc., 69, 1393-1401 (1947), 21.4 g of phthalic anhydride (0.145 mol) were added to a suspension of taurine (17 g, 0.137 mol) and potassium acetate (14.2 g, 0.145 mol) in glacial acetic acid (48 mL), heated under reflux. Heating was continued to obtain the complete dissolution of the reagents (2.5 h); after cooling to 0°-5° C., a precipitate formed which was separated by filtration, washed with glacial acetic acid and absolute ethanol, dried in the air and under vacuum (50° C.), to give 31.2 g of 2-phthalimidoethanesulfonic acid potassium salt [m.p. >300° C.; 1H-NMR (D2O) d 7.85 (m, 4H), 4.05 (t, 3H, J=8 Hz), 3.25 (t, 2H, J=8 Hz). A suspension of 5 g of the salt in benzene (50 mL), dried by azeotropical distillation, was added with 2.56 g of phosphorous pentachloride (0.015 mol) and refluxed for 1 h. Then a second aliquot of phosphorous pentachloride (2.56 g, 0.015 mol) was added. The mixture was refluxed for a further 90 min, then solvents and reagents were evaporated off under vacuum and reduced pressure. The mixture was refluxed for a further 1.30 hours; cooled to r.t. and the solvents were evaporated under reduced pressure. The residue was taken up into 30 g of finely triturated ice to form a fine solid (which was filtered, washed with water and dried) of 2-phthalimidoethanesulfonyl chloride (3.71 g; m.p. 158-159° C.).

Provenance & Evidence