Process for making 2-amino-2-imidazoline, guanidine and 2-amino-3,4,5,6-tetrahydropyrimidine derivatives

US6066740A · kind A · utility

Assignee

• The Procter & Gamble Company · US

Inventors

• Michael Selden Godlewski · Loveland, US
• Sean Rees Klopfenstein · Loveland, US
• Sreenivasa Reddy Mundla · Hyderabad, IN
• William Seibel · Kyles, US
• Randy Stuart Muth · Poolville, US

Key dates

• Filing date: Nov 25, 1997
• Grant date: May 23, 2000
• Expiry date: Nov 25, 2017

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D417/12
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention provides a process for making 2-amino-2-imidazoline, guanidine, and 2-amino-3,4,5,6-tetrahydroyrimidine derivatives by preparing the corresponding activated 2-thio-subsituted-2-derivative in a two-step, one-pot procedure and by further reacting yields this isolated derivative with the appropriate amine or its salts in the presence of a proton source. The present process allows for the preparation of 2-amino-2-imidazolines, quanidines, and 2-amino-3,4,5,6-tetrahydropyrimidines under reaction conditions that eliminate the need for lengthy, costly, or multiple low yielding steps, and highly toxic reactants. This process allows for improved yields and product purity and provides additional synthetic flexibility.