N-substituted cis-n-propenyl-acetamides, and process for their preparation
AssigneeBayer Aktiengesellschaft
InventorReinhard Lantzsch
Life of this patent
Estimating the term…
Abstract
The present invention relates to new N-substituted cis-N-propenyl-acetamides of the general formula (I) ##STR1## in which R.sup.1 represents in each case optionally substituted alkyl, -C(alkyl).sub.2 -alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aralkyl or hetarylalkyl; a process for their preparation, and their use for the preparation of 2-chloro-5-methyl-pyridine.
Claims14
N-substituted cis-N-propenyl-acetamides of the formula (I) ##STR15## in which R.sup.1 represents in each case optionally substituted alkyl, -C(alkyl).sub.2 -alkenyl, alkynyl, cycloalkyl, cycloalkyalkyl, aralkyl or hetarylalkyl, wherein the N-substituted cis-N-propenyl-acetamides are essentially free of the trans isomers.
Process for the preparation of N-substituted cis-N-propenyl-acetamides of the formula (I) ##STR16## in which R.sup.1 represents in each case optionally substituted alkyl, -C(alkyl).sub.2 -alkenyl, alkynyl, cycloalkyl, cycloalkyalkyl, aralkyl or hetarylalkyl,
- wherein acetamides of the formula (II) ##STR17## in which R.sup.1 has the abovementioned meaning
- are isomerized using strong bases in the presence of an aprotic polar diluent or in the absence of a diluent.
A method for the preparation of 2-chloro-5-methyl-pyridine, of the formula (IV) ##STR18## by reaction of an N-substituted cis-N-propenyl-acetamide of the formula ##STR19## in which R.sup.1 represents in each case optionally substituted alkyl, -C(alkyl).sub.2 -alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aralkyl or hetarylalkyl
- with a formamide derivative of the formula (III) ##STR20## in which R.sup.2 and R.sup.3 are identical or different and represent alkyl or cycloalkyl, or together represent alkanediyl,
- and with a chlorinating agent, at temperatures between 20.degree. and 150.degree. C., if optionally in the presence of a diluent.
N-substituted cis-N-propenyl-acetamides of the formula (I) ##STR21## in which R.sup.1 represents in each case optionally substituted alkyl, -C(alkyl).sub.2 -alkenyl, alkynyl, cycloalkyl, cycloalkyalkyl, aralkyl or hetarylalkyl, wherein the N-substituted cis-N-propenyl-acetamides are at least 87.5% free of the trans isomers.
Dependencies are inferred from the claim text.