Acetic Acid → HCID 20399521, compound

Participants

Reaction Steps

20 g of 2-(4-dibenzylamino-2-hydroxy-5-methylphenyl)-propionic acid dibenzylamide are heated under reflux for 3 hours in 40 ml of 2N hydrochloric acid and 40 ml of glacial acetic acid. The mixture is then concentrated to dryness by evaporation in vacuo and the residue is partitioned between ether and 1N sodium hydroxide solution. Acidification to a pH of 1 with hydrochloric acid and extraction yields 2-(4-dibenzylamino-2-hydroxy-5-methylphenyl)-propionic acid which, for purification, is chromatographed over silica gel in methylene chloride. The colourless crystals melt at 174°-175°. 15 g of the crystals are dissolved in 50 ml of ether and 6 g of dicyclohexylcarbodiimide are added thereto. After 30 minutes the urea formed is filtered off and the filtrate is concentrated to dryness by evaporation. In this manner 6-dibenzylamino-3,5-dimethylbenzofuran-2(3H)-one having a melting point of 122°-123° is obtained.

Provenance & Evidence