Ethanolamine → N-(2-hydroxyethyl)-N-(2-hydroxypropyl)-4,4,4-trichloro-2-hydroxy-1-butylamine

Participants

Reaction Steps

To a solution of 30.6g (0.5 mole) monoethanolamine in 150 ml isopropanol heated to reflux was slowly added 33.8g (0.58 mole) propylene oxide over a period of about one hour. After refluxing the mixture overnight the solvent and unreacted starting material were distilled off, affording a residue weighing 49.1g. To this residue was added 5.7g of the unreacted monoethanolamine distillate. To this mixture was added 90g (0.51 mole) 4,4,4-trichloro-1,2-epoxybutane over a period of 45 minutes. An equivolume amount of methanol was then added and the reaction mixture refluxed overnight. Evaporation of the solvent yielded 140.8g (95.5%) of N-(2-hydroxyethyl)-N-(2-hydroxypropyl)-4,4,4-trichloro-2-hydroxy-1-butylamine, a brown viscous liquid very soluble in methanol but only slightly soluble in water(pH 7-8); hydroxyl number = 564. Analysis: (Calculated) %N 4.79; %Cl, 36.35. (Found) %N, 4.56; %Cl, 36.92.

Provenance & Evidence