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US 6,472,535 B1Granted
Oxidative hydrolysis of heteroaromatic thiones
AssigneeBayer Aktiengesellschaft
InventorDavid T. Erdman
Life of this patent
Estimating the term…
Abstract
A process for preparing a triazolinone includes the step of reacting a triazolinethione with an oxidant at a temperature range of from about 60° C. to about 100° C. in the presence of a base.
Claims17
A process for preparing a triazolinone of the formula:
- wherein
- R1 represents alkyl having 1 to 6 carbon atoms which is optionally substituted by halogen, cyano or C1-C4 alkoxy, or represents cycloalkyl having 3 to 6 carbon atoms which is optionally substituted by halogen, cyano or C1-C4-alkyl, and
- R2 represents amino, or a radical selected from the group consisting of alkyl, alkenyl, alkinyl, alkoxy, alkylamino or dialkylamino, each or which has up to 6 carbon atoms in the alkyl, alkenyl or alkinyl groups and each of which is optionally substituted by halogen, cyano or C1-C4-alkoxy, or represents a radical selected from the group consisting of C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C2-alkyl or phenyl, each of which is optionally substituted by halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkoxycarbonyl,
- comprising the steps of mixing a triazolinethione of the formula
- wherein R1 and R2 are as defined above in this claim 1,
- with an oxidant at a temperature range of from about 60° C. to about 100° C. in the presence of a base;
- and
- reacting the mixture of said triazolinethione, said oxidant and said base for a time of from about 1 hour to about 6 hours, at a molar ratio of triazolinethione to oxidant to base of from about 1:5:4 to about 1:20:10,
- wherein said mixture of said triazolinethione, said oxidant and said base has a basic pH in the range of about 10 to 14 and wherein said triazolinone is formed without changing said mixture to an acidic pH.
6 more elements
A process for preparing a triazolinone of the formula:
- wherein
- R1 represents alkyl having 1 to 6 carbon atoms which is optionally substituted by halogen, cyano or C1-C4-alkoxy, or represents cycloalkyl having 3 to 6 carbon atoms which is optionally substituted by halogen, cyano or C1-C4-alkyl, and
- R2 represents amino, or a radical selected from the group consisting of alkyl, alkenyl, alkinyl, alkoxy, alkylamino or dialkylamino, each or which has up to 6 carbon atoms in the alkyl, alkenyl or alkinyl groups and each of which is optionally substituted by halogen, cyano or C1-C4-alkoxy, or represents a radical selected from the group consisting of C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C2-alkyl or phenyl, each of which is optionally substituted by halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkoxycarbonyl, comprising the steps of
- (a) mixing solvent, base and a triazolinethione of the formula
- wherein R1 and R2 are as defined above in this claim 9,
- (b) adding an oxidant to the solvent, base and triazolinethione to form a reaction mixture, and
- (c) heating the reaction mixture,
- wherein said reaction mixture of said solvent, said base, said triazolinethione, and said oxidant has a basic pH in the range of about 10 to 14 and wherein said triazolinone is formed without changing said reaction mixture to an acidic pH.
5 more elements
Dependencies are inferred from the claim text.