Process for the preparation of 3-(N-aryl-amino)-propyl-2'-sulfatoethyl-sulfonyl compounds

US5672738A · kind A · utility

Assignee

• Hoechst GmbH · DE

Inventors

• Christian Schumacher · Frankfurt am Main, DE
• Michael Meier · Frankfurt am Main, DE
• Werner Russ · Flörsheim, DE

Key dates

• Filing date: Nov 17, 1995
• Grant date: Sep 30, 1997
• Expiry date: Nov 17, 2015

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D265/10
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Process for the preparation of 3-(N-aryl-amino)-propyl-2'-sulfatoethyl-sulfonyl compounds Compounds of the formula (1) EQU Ar--NH--(CH.sub.2).sub.3 --SO.sub.2 --(CH.sub.2).sub.2 --OSO.sub.3 M(1) are prepared by reacting a compound of the formula (2) ##STR1## with 2-mercaptoethanol to give a compound of the formula (3) EQU Ar--NH--(CH.sub.2).sub.3 --S--(CH.sub.2).sub.2 --OH (3) at temperatures from 90.degree. to 270.degree. C. in the presence of a catalytic amount of a base, subsequently oxidizing the compound of the formula (3) to give a compound of the formula (4) EQU Ar--NH--(CH.sub.2).sub.3 --SO.sub.2 --(CH.sub.2).sub.2 --OH(4), and finally esterifying the compound of the formula (4) with at least one molar equivalent of sulfuric acid, oleum or halosulfonic acid to give a compound of the formula (1). Compounds of the formula (1) are valuable starting compounds for the preparation of reactive dyestuffs.