Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2000-12-27
2002-10-22
Shippen, Michael L. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C548S228000, C562S444000, C562S449000, C562S450000, C564S170000
Reexamination Certificate
active
06469210
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a process for producing a phenylalkanoic acid amide compound and an intermediate for producing the compound.
BACKGROUND ART
Some of the phenylalkanoic acid amides are known to be useful as an effective ingredient for fungicide (for example, JP-A-9-48750 and Japanese Patent Application No. 10-296078); however, no process is known for producing such a phenylalkanoic acid amide compound from an oxazolinone compound.
The present invention aims at providing a process for simple and easy production of a phenylalkanoic acid amide compound having an excellent fungicidal activity.
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 found out that the intended phenylalkanoic acid amide compound can be produced by reacting an oxazolinone compound with methyllithium or a methylmagnesium halide and the above aim can be achieved. The present invention has been completed based on the above finding.
BEST MODE FOR CARRYING OUT THE INVENTION
The present invention is described in detail below.
The above aim of the present invention has been achieved by providing the inventions shown in the following [1] to [8].
[1] A process for producing a phenylalkanoic acid amide represented by the following general formula [3]
(wherein X is a hydrogen atom, an alkyl group, an alkoxy group, a haloalkyl group or a halogen atom; n is an integer of 1 to 3; when n is 2 or more, a plurality of Xs may be the same or different; and Y and Z are each independently a halogen atom or a hydrogen atom or the like), which process comprises reacting a carboxylic acid compound represented by the following general formula [1]
(wherein X is a hydrogen atom, an alkyl group, an alkoxy group, a haloalkyl group or a halogen atom; n is an integer of 1 to 3; when n is 2 or more, a plurality of Xs may be the same or different; and Y and Z are each independently a halogen atom or a hydrogen atom) with a dehydrating agent to produce an oxazolinone compound represented by the following general formula [2]
(wherein X is a hydrogen atom, an alkyl group, an alkoxy group, a haloalkyl group or a halogen atom; n is an integer of 1 to 3; when n is 2 or more, a plurality of Xs may be the same or different; and Y and Z are each independently a halogen atom or a hydrogen atom) and then reacting the oxazolinone compound with methyllithium or a methylmagnesium halide.
[2] A carboxylic acid compound represented by the following general formula [1]
(wherein X is a hydrogen atom, an alkyl group, an alkoxy group, a haloalkyl group or a halogen atom; n is an integer of 1 to 3; when n is 2 or more, a plurality of Xs may be the same or different; and Y and Z are each independently a halogen atom or a hydrogen atom).
[3] An oxazolinone compound represented by the following general formula [2]
(wherein X is a hydrogen atom, an alkyl group, an alkoxy group, a haloalkyl group or a halogen atom; n is an integer of 1 to 3; when n is 2 or more, a plurality of Xs may be the same or different; and Y and Z are each independently a halogen atom or a hydrogen atom).
[4] A process for producing an oxazolinone compound represented by the following general formula [2]
(wherein X is a hydrogen atom, an alkyl group, an alkoxy group, a haloalkyl group or a halogen atom; n is an integer of 1 to 3; when n is 2 or more, a plurality of Xs may be the same or different; and Y and Z are each independently a halogen atom or a hydrogen atom), which process comprises reacting a carboxylic acid compound represented by the following general formula [1]
(wherein X is a hydrogen atom, an alkyl group, an alkoxy group, a haloalkyl group or a halogen atom; n is an integer of 1 to 3; when n is 2 or more, a plurality of Xs may be the same or different; and Y and Z are each independently a halogen atom or a hydrogen atom) with a dehydrating agent.
[5] A process for producing a phenylalkanoic acid amide represented by the following general formula [3]
(wherein X is a hydrogen atom, an alkyl group, an alkoxy group, a haloalkyl group or a halogen atom; n is an integer of 1 to 3; when n is 2 or more, a plurality of Xs may be the same or different; and Y and Z are each independently a halogen atom, a hydrogen atom or the like), which process comprises reacting an oxazolinone compound represented by the following general formula [2]
(wherein X is a hydrogen atom, an alkyl group, an alkoxy group, a haloalkyl group or a halogen atom; n is an integer of 1 to 3; when n is 2 or more, a plurality of Xs may be the same or different; and Y and Z are each independently a halogen atom, a hydrogen atom or the like) with methyllithium or a methylmagnesium halide.
[6] A process for producing a phenylalkanoic acid amide, set forth in the above [1], wherein the dehydrating agent is an acid anhydride, a thionyl halide compound, a phosphorus halide compound or a halocarbonic acid ester compound.
[7] A process for producing a phenylalkanoic acid amide, set forth in the above [1], wherein the methylmagnesium halide is methylmagnesium chloride or methylmagnesium bromide.
[8] A process for producing a phenylalkanoic acid amide, set forth in the above [1], wherein the dehydrating agent is an acid anhydride, a thionyl halide compound, a phosphorus halide compound or a halocarbonic acid ester compound and the methylmagnesium halide is methylmagnesium chloride or methylmagnesium bromide.
The present invention is described in detail below.
The process of the present invention described in the above [1] is constituted by a step of reacting a carboxylic acid compound represented by the above general formula [1] (which is the present invention compound described in the above [2]) with a dehydrating agent to give rise to intramolecular ring closure to produce an oxazolinone compound represented by the general formula [2] (which is the present invention compound described in the above [3]) (this step is referred to as step 1 and corresponds to the present invention process described in the above [4]) and a step of reacting the oxazolinone compound represented by the general formula [2] with methyllithium or a methylmagnesium halide to give rise to ring opening of oxazolinone ring to produce a phenylalkanoic acid amide compound represented by the general formula [3] which is an intended final product (this step is referred to as step 2 and corresponds to the present invention process described in the above [5]).
Description is made first on the production of a carboxylic acid compound represented by the general formula [1], which is used as a raw material in the step 1 of the present invention process. The carboxylic acid compound represented by the general formula [1] is a novel compound and is useful as a raw material used in production of the oxazolinone compound represented by the general formula [2], which is an intended compound in the step 1.
The carboxylic acid compound represented by the general formula [1], used in the present invention can be produced by reacting an ester compound represented by the following general formula [4], with an acid or a base in the presence of water to hydrolyze the ester moiety of the ester compound.
In the above formula [4], R is a straight chain or branched chain alkyl group of 1 to 6 carbon atoms (hereinafter, carbon atoms are abbreviated to, for example, C1 to C6 in the case of 1 to 6 carbon atoms), such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, n-hexyl group or the like; a C3 to C6 cycloalkyl group such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group or the like; a
Hiyoshi Hidetaka
Matsumoto Katsunori
Taniguchi Shuji
Ihara Chemical Industry Co. Ltd.
Kubovcik & Kubovcik
Shippen Michael L.
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