Acrylic Acid → 3-(2-Indolylthio)Propionic Acid

Participants

Reaction Steps

One liter of triethylamine is added slowly in the course of 2 hours 30 minutes to a vigorously stirred suspension of 194 g (1.3 mol) of 2-indolinethione (prepared according to Y. Nakisumi and Coll. Chem. Pharm. Bull. 1984, 32, (3), 877) in 108 g (1.5 mol) of acrylic acid. The mixture is brought to reflux for 12 hours while stirring is maintained, and then cooled and concentrated under vacuum. The residue is taken up with 10% strength aqueous sodium bicarbonate solution and the mixture is filtered. The filtrate is acidified with aqueous hydrochloric acid solution. The precipitate formed is drained, washed with water and dried. It is recrystallized in toluene.

Provenance & Evidence