Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
2000-12-27
2003-01-07
Rotman, Alan L. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C560S155000, C564S123000
Reexamination Certificate
active
06504046
ABSTRACT:
TECHNICAL FIELD
The present invention relates to an amide compound which is a useful intermediate in production of a phenylalkanoic acid amide useful as a fungicide; a process for production thereof; a process for production of an oxazolinone compound which is a raw material used in production of said amide compound; and a process for production of a ketone compound which is also a useful intermediate in production of a phenylalkanoic acid amide from said amide compound.
BACKGROUND ART
Some of the phenylalkanoic acid amides are known to be useful as an effective fungicide (for example, JP-A-9-48750); however, no process is known for producing such a phenylalkanoic acid amide compound from an oxazolinone compound.
As the process for producing an oxazolinone compound, a process is generally known which comprises subjecting an amino acid whose amino group is protected with acyl group, to dehydrative cyclization (Protective Groups in Organic Synthesis, p. 223, 1981, John Wiley & Sons). Besides, a process is also known which comprises producing an oxazolinone from an acylated aminonitrile using oxalyl chloride or chlorooxoacetate (Tetrahedron, Vol. 40, pp. 2395 to 2404, 1984). These processes, however, have drawbacks in that it is difficult to obtain a corresponding amino acid or impossible to produce an intended oxazolinone compound at a low cost industrially.
The present invention aims at providing important intermediates used in production of a phenylalkanoic acid amide compound showing an excellent fungicidal effect; and novel and simple processes for producing such an intermediate or a raw material compound used in production of the intermediate.
DISCLOSURE OF THE INVENTION
The present inventor made a hard study zealously in order to solve the above subject. As a result, the present inventor surprisingly found out that an amide compound which is an important intermediate for phenylalkanoic acid amide compound can be easily formed by reacting an oxazolinone compound with a carboxy compound (e.g. malonic acid half ester) in the presence of a base. The present inventor also found out that the above oxazolinone compound can be obtained by a simple process of reacting a nitrile compound of high availability with an acid. The present invention has been completed based on the above findings.
BEST MODE FOR CARRYING OUT THE INVENTION
The present invention is described in detail below.
The present invention provides the inventions described in the following [1] to [6].
[1] A process for producing an amide compound represented by the following general formula
[wherein R is an alkyl group, a cycloalkyl group, a haloalkyl group, an aryl group, a substituted aryl group, an arylalkyl group, a substituted arylalkyl group, an (aryl)(alkoxy)alkyl group or a (substituted aryl)(alkoxy)alkyl group; R
1
and R
2
where each independently an alkyl group, a cycloalkyl group, a haloalkyl group, an arylalkyl group, a substituted arylalkyl group, an aryl group, a substituted aryl group or a hydrogen atom, and may bond with each other to form a ring together with the carbon atom with which they bond; and R
3
is an alkyl group, a cycloalkyl group, a haloalkyl group, an arylalkyl group, a substituted arylalkyl group, an aryl group, a substituted aryl group or a hydrogen atom], which process comprises reacting a nitrile compound represented by the following general formula
(wherein R, R
1
and R
2
each have the same definition as given above) with an acid to give rise to intramolecular ring closure to obtain an oxazolinone compound represented by the following general formula
(wherein R, R
1
and R
2
each have the same definition as given above), and reacting the oxazolinone compound with a carboxy compound represented by the following general formula
(wherein Y is a hydrogen atom, a carboxyl group or a salt of the carboxyl group; and R
3
has the same-definition as given above) in the presence of a base.
[2] A process for producing an oxazolinone compound represented by the following general formula
[wherein R is an alkyl group, a cycloalkyl group, a haloalkyl group, an aryl group, a substituted aryl group, an arylalkyl group, a substituted arylalkyl group, an (aryl)(alkoxy)alkyl group or a (substituted aryl)(alkoxy)alkyl group; and R
1
and R
2
are each independently an alkyl group, a cycloalkyl group, a haloalkyl group, an arylalkyl group, a substituted arylalkyl group, an aryl group, a substituted aryl group or a hydrogen atom, and may bond with each other to form a ring together with the carbon atom with which they bond], which process comprises reacting a nitrile compound represented by the following general formula
(wherein R, R
1
and R
2
each have the same definition as given above) with an acid to give rise to intramolecular ring closure.
[3] A process for producing an amide compound represented by the following general formula
[wherein R is an alkyl group, a cycloalkyl group, a haloalkyl group, an aryl group, a substituted aryl group, an arylalkyl group, a substituted arylalkyl group, an (aryl)(alkoxy)alkyl group or a (substituted aryl)(alkoxy)alkyl group; R
1
and R
2
are each independently an alkyl group, a cycloalkyl group, a haloalkyl group, an arylalkyl group, a substituted arylalkyl group, an aryl group, a substituted aryl group or a hydrogen atom, and may bond with each other to form a ring together with the carbon atom with which they bond; and R
3
is an alkyl group, a cycloalkyl group, a haloalkyl group, an arylalkyl group, a substituted arylalkyl group, an aryl group, a substituted aryl group or a hydrogen atom], which process comprises reacting an oxazolinone compound represented by the following general formula
(wherein R, R
1
and R
2
each have the same definition as given above) with a carboxy compound represented by the following general formula
(wherein Y is a hydrogen atom, a carboxyl group or a salt of the carboxyl group; and R
3
has the same definition as given above) in the presence of a base.
[4] A process for producing a ketone compound represented by the following general formula
[wherein R
1
and R
2
are each independently an alkyl group, a cycloalkyl group, a haloalkyl group, an arylalkyl group, a substituted arylalkyl group, an aryl group, a substituted aryl group or a hydrogen atom, and may bond with each other to form a ring together with the carbon atom with which they bond; and R
4
is an alkylcarbonyl group, a cycloalkylcarbonyl group, a haloalkylcarbonyl group, an arylcarbonyl group, a substituted arylcarbonyl group, an arylalkylcarbonyl group, a substituted arylalkylcarbonyl group, an (aryl)(alkoxy)alkylcarbonyl group, a (substituted aryl)(alkoxy)alkylcarbonyl group or a hydrogen atom], which process comprises reacting an amide compound represented by the following general formula
[wherein R is an alkyl group, a cycloalkyl group, a haloalkyl group, an aryl group, a substituted aryl group, an arylalkyl group, a substituted arylalkyl group, an (aryl)(alkoxy)alkyl group or a (substituted aryl)(alkoxy)alkyl group; R
1
and R
2
each have the same definition as given above; and R
3
is an alkyl group, a cycloalkyl group, a haloalkyl group, an arylalkyl group, a substituted arylalkyl group, an aryl group, a substituted aryl group or a hydrogen atom] with an acid or a base in the presence of water.
[5] A process for producing an amide compound, set forth in the above [1] or [3], wherein the base is selected from alkali metal bases, alkaline earth metal bases, organic amines and pyridines.
[6] An acid amide compound represented by the following general formula
[wherein R
5
is an alkyl group, a cycloalkyl group, a haloalkyl group, an arylalkyl group, a substituted arylalkyl group, an (aryl)(alkoxy)alkyl group or a (substituted aryl)(alkoxy)-alkyl group; and R
1
and R
2
are each independently an alkyl group, a cycloalkyl group, a haloalkyl group, an arylalkyl group, a substituted arylalkyl group,
Hiyoshi Hidetaka
Suzuki Junko
Taniguchi Shuji
Ihara Chemical Industry Co. Ltd.
Kubovcik & Kubovcik
Reyes Hector M
Rotman Alan L.
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