Preparation of carboxylate and sulfonate salts of 1-cis-(3-chloro-2-propenyl)-3,5,7-triaza-1-azoniatricyclo(3.3.1.1.sup.3, 7)decane-II

USRE29226E · kind E · reissue

Assignee

• THE DOW CHEMICAL COMPANY · US

Inventors

• Albertha M. Paul nee Albertha B. Mitchell · Holliston, US
• Charles E. Moppett · Mystic, US
• Thomas P. Brady · Methuen, US

Key dates

• Filing date: Jan 26, 1976
• Grant date: May 17, 1977
• Expiry date: Jan 26, 1996

Classification

• Technology area (CPC —): General

Abstract

Compounds of the .[.formulas.]. .Iadd.formula .Iaddend. ##STR1## wherein X.sup.- is a lower alkyl carboxylate .[.(I).]., a phenylcarboxylate .[.(I).]., a lower alkylsulfonate .[.(II).]. or a phenylsulfonate .[.(II).]. anion, wherein the phenyl ring may have lower alkyl, lower alkoxy, hydroxyl, amino, nitro, bromo or chloro substitution. The compounds are prepared by reacting the .[.carbinolamine.]. .Iadd.ring-opened intermediate .Iaddend.prepared by reacting cis-1-(3-chloro-2-propenyl)-3,5,7-triaza-1-azoniatricyclo(3.3.1.1.sup.3,7) decane chloride with aqueous sodium hydroxide, with a carboxylic or sulfonic acid, as indicated, to form the corresponding 1-cis-(3-chloro-2-propenyl)-3,5,7-triaza-1-azoniatricyclo(3.3.1.1.sup.3,7) decane carboxylate or sulfonate. These compounds have antimicrobial activity.