Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1999-07-19
2001-03-20
Higel, Floyd D. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
06204390
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a synthesizing method for a 3-substituted-3-oxo-2-(2,4-oxazolidinedione-3-yl)propionic acid amide compound.
Said 3-substituted-3-oxo-2-(2,4-oxazolidinedione-3-yl)propionic acid amide compound is an important compound as a yellow coupler used in a silver halide photographic light-sensitive material, or as its intermediate compound, or as an intermediate manufacturing compound for medical compounds.
BACKGROUND OF THE INVENTION
As the synthesizing methods for said 3-substituted-3-oxo-2-(2,4-oxazolidinedione-3-yl)propionic acid amide compound, the following methods are conventionally proposed:
(1) a synthesizing method for obtaining said 3-substituted-3-oxo-2-(2,4-oxazolidinedione-3-yl)propionic acid amide compound by reacting 3-substituted-3-oxo-2-chloropropionic acid amides with potassium salts of 2,4-oxazolidinediones in acetonitrile (described in Japanese Patent Publication Open to Public Inspection (hereinafter referred to as JP-A) No. 48-66835);
(2) a synthesizing method for obtaining said 3-substituted-3-oxo-2-(2,4-oxazolidinedione-3-yl)propionic acid amide compound by reacting the 3-substituted-3-oxo-2-chloropropionic acid amides with the 2,4-oxazolidinediones in the presence of potassium hydroxide (described in JP-A No. 52-115219);
(3) a synthesizing method for obtaining said 3-substituted-3-oxo-2-(2,4-oxazolidinedione-3-yl)propionic acid amide compound by reacting the 3-substituted-3-oxo-2-chloropropionic acid amides with the 2,4-oxazolidinediones in the presence of potassium carbonate (described in JP-A No. 4-124661).
In these conventional synthesizing methods for said 3-substituted-3-oxo-2-(2,4-oxazolidinedione-3-yl)propionic acid amide compound, either a reaction by the use of salts of the 2,4-oxazolidinediones or a reaction in the presence of inorganic base is employed. In the former case, since it is necessary that the salts of the 2,4-oxazolidinediones are previously prepared or isolated, consequently the synthesizing is rather complex.
On the other hand, in the latter case, the reaction in the presence of the inorganic base has an adverse effect such that said reaction is accompanied by unpreferable side reactions, specifically in the later synthesizing processes, and consequently the reaction yield is lowered.
SUMMARY OF THE INVENTION
Accordingly, an object of the present invention is to provide a synthesizing method for a 3-substituted-3-oxo-2-(2,4-oxazolidinedione-3-yl)propionic acid amide compound at a high yield, as well as ease in synthesizing it.
DETAILED DESCRIPTION OF THE INVENTION
The above-mentioned object of the present invention can be attained by the following method:
(1) A synthesizing method for obtaining a 3-substituted-3-oxo-2-(2,4-oxazolidinedione-3-yl)propionic acid amide compound represented by the following Formula [I], by reacting a compound represented by the following Formula [II] with a compound represented by the following Formula [III], in the presence of an organic base;
wherein, R
1
represents an alkyl group, a cycloalkyl group, an aryl group, an amino group or a heterocyclic group; R
2
represents a chlorine atom, an alkoxy group or an aryloxy group; R
3
represents a substituent group; n represents an integer of 0 to 4; when n represents an integer of at least 2, plural R
3
may be the same or different; R
4
and R
5
each represent a hydrogen atom, an alkyl group or an aryl group; while X represents a chlorine atom or a bromine atom.
(2) The synthesizing method for obtaining said 3-substituted-3-oxo-2-(2,4-oxazolidinedione-3-yl)propionic acid amide compound of Item 1, wherein the boiling point of said organic base is between 120° C. -190° C.
(3) The synthesizing method for obtaining said 3-substituted-3-oxo-2-(2,4-oxazolidinedione-3-yl)propionic acid amide compound of Item 1, wherein R
5
of said 3-substituted-3-oxo-2-(2,4-oxazolidinedione-3-yl)propionic acid amide compound represented by the Formula [I] is a hydrogen atom.
The present invention will be explained below in detail.
First, the compound represented by Formula [I], Formula [II] and Formula [III] will be explained in detail.
In Formula [I] and Formula [II], examples of an alkyl group represented by R
1
include a methyl group, an ethyl group, an iso-propyl group, a t-butyl group and a dodecyl group, etc. These alkyl groups may have a substituent group, and examples of said substituent group include, for example, a halogen atom, an aryl group, an alkoxy group, an aryloxy group, an alkylsulfonyl group, an acylamino group and a hydroxy group, etc.
Examples of a cyclohexyl group represented by R
1
include a cyclopropyl group, a cyclohexyl group and an adamantyl group, etc.
As an aryl group represented by R
1
, can be cited an aryl group having 6 to 14 carbon atoms (for example, a phenyl group, a 1-naphthyl group and a 9-anthranyl group, etc.). Said aryl group represented by R
1
can further contain a substituent group, and examples of said substituent group include a nitro group, a cyano group, an amino group (for example, a dimethylamino group and an anilino group, etc.), an alkylthio group (for example, a methylthio group, etc.), the same alkyl group as defined for the above-mentioned R
1
, and the same substituent group as defined for the substituent group which the alkyl group represented by the above-mentioned R
1
can contain.
Examples of an amino group include an unsubstituted amino group and a substituted amino group such as a diethylamino group, a di-iso-octylamino group and an anilino group, etc. These amino groups can further contain a substituent group, and said substituent group includes the same substituent group as defined for the substituent group which the alkyl group represented by the above-mentioned R
1
can contain.
Examples of a heterocyclic group represented by R
1
include a morpholino group and an indoline-1-yl group, etc.
Examples of an alkoxy group represented by R
2
include a methoxy group, an ethoxy group, an iso-propoxy group, a butoxy group, a decyloxy group and a dodecyloxy group, etc., and as an aryloxy group represented by R
2
, a phenoxy group is representative.
In Formula [I] and Formula [II], R
3
represents a substituent group, and any substituent which can substitute on a benzene ring can be used without limitation. Examples of said substituent include the same alkyl group, cycloalkyl group and aryl group as defined for R
1
, and additionally an alkyl group substituted with a halogen atom (for example, a trifluoromethyl group, etc.), a halogen atom (for example, a chlorine atom, a bromine atom, etc.), a cyano group, a nitro group, an alkenyl group (for example, a 2-propylene group, an oleyl group, etc.), a hydroxy group, an alkoxy group (for example, a methoxy group, a 2-ethoxyethoxy group, etc.), an aryloxy group (for example a phenoxy group, a 2,4-di-tert-amylphenoxy group, 4-(4-hydroxyphenylsulfonyl)phenoxy group, etc.), a heterocyclicoxy group (for example, a 4-pyridyloxy group, a 2-hexahydropyranyloxy group, etc.), a carbonyloxy group (for example, an alkylcarbonyloxy group such as an acetyloxy group, a trifluoroacetyloxy group, a pivaloyloxy group, etc., an aryloxy group such as a benzoyloxy group, a pentafluorobenzoyloxy group, etc.), a sulfonyloxy group (for example, an alkylsulfonyloxy group such as a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a n-dodecanesulfonyloxy group, etc., an arylsulfonyloxy group such as a benzenesulfonyloxy group, a p-toluenesulfonyloxy group, etc.), a carbonyl group (for example, an alkylcarbonyl group such as an acetyl group, a trifluoroacetylpivaloyl group, etc., an arylcarbonyl group such as a benzoyl group, a pentafluorobenzoyl group, a 3,5-di-tert-butyl-4-hydroxybenzoyl group, etc.), an oxycarbonyl group (for example, an alkoxycarbonyl group such as a methoxycarbonyl group, a cyclohexyloxycarbonyl group, a n-dodecyloxycarbonyl group, etc., an aryloxycarbonyl group such as a phenoxycarbonyl group, a 2,4-di-ter
Ikesu Satoru
Kimura Kazuhiko
Ota Katsuji
Frishauf, Holtz Goodman, Langer & Chick, P.C.
Higel Floyd D.
Konica Corporation
Wright Sonya R.
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