Process for the preparation of 3'-aminopropyl 2-sulfatoethyl sulfone

US5416234A · kind A · utility

Assignee

• Hoechst GmbH · DE

Inventors

• Michael Meier · Frankfurt am Main, DE
• Heinrich Angenendt · Frankfurt am Main, DE
• Georg Grotsch · Bad Soden am Taunus, DE

Key dates

• Filing date: Aug 25, 1993
• Grant date: May 16, 1995
• Expiry date: Aug 25, 2013

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C317/28
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Process for the preparation of 3'-aminopropyl 2-sulfatoethyl sulfone in high yield, which comprises reacting allylamine with mercaptoethanol in aqueous sulfuric acid in a one-pot process at temperatures from about 25.degree. C. to the boiling point of the reaction mixture in the presence of free-radical initiators which are soluble in the reaction medium, oxidizing the reaction mixture thus obtained with hydrogen peroxide in the presence of catalytic amounts of a compound of a transition metal of the periodic table of elements as oxidation catalyst to give 3'-aminopropyl 2-hydroxyethyl sulfone hemisulfate, adding further sulfuric acid until the total amount of sulfuric acid in the mixture is at least 1 mol, relative to the allylamine used, and esterifying the 3'-aminopropyl 2-hydroxyethyl sulfone hemisulfate obtained after oxidation by evaporation to dryness or with sulfuric acid or oleum or chlorosulfonic acid in solution.