Di(3-(2-chloroethylsulfonyl)-1-propyl)amine hydrochloride and a process for its preparation

US5446201A · kind A · utility

Assignee

• Hoechst GmbH · DE

Inventors

• Heinrich Angenendt · Frankfurt am Main, DE
• Michael Meier · Frankfurt am Main, DE
• Wolfram Schams · Frankfurt am Main, DE

Key dates

• Filing date: Nov 30, 1993
• Grant date: Aug 29, 1995
• Expiry date: Nov 30, 2013

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C09B62/4413
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Process for preparing di(3-(2-chloroethylsulfonyl)-1-propyl)amine hydrochloride, by PA1 reacting 1 mol of an N,N-diallylcarboxamide of the formula (1) EQU R-CON(CH.sub.2 --CH.dbd.CH.sub.2).sub.2 (1) PA1 in which R is hydrogen, alkyl(C.sub.1 -C.sub.6) or cycloalkyl(C.sub.4 -C.sub.8) with about 4 to about 8 mol of mercaptoethanol at temperatures of about 0.degree. to about -70.degree. C. in the presence of pure oxygen or a mixture of oxygen with an inert gas or an inert gas mixture, if appropriate in an inert organic solvent, to give the carboxamide of the formula (2) EQU R--CON(CH.sub.2 --CH.sub.2 --CH.sub.2 --S--CH.sub.2 --CH.sub.2 --OH).sub.2(2) PA1 in which R has the abovementioned meaning, PA1 hydrolyzing this compound with the aqueous solution of an alkaline agent at temperatures of about 40.degree. to about 120.degree. C. at a pH of about 10 to about 14, and PA1 reacting 1 mol of the di(3-(2-hydroxyethylthio)-1-propyl)amine thus obtained with about 4 to about 6 mol of chlorine gas in about 2 to about 15% hydrochloric acid at temperatures of about 20.degree. to about 110.degree. C. to give di(3-(2-chloroethylsulfonyl)-1-propyl)amine hydrochloride.