JP2002326989A - Method for producing phthalisoimide derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for producing a phthalisoimide derivative. SOLUTION: This method for producing the phthalisoimide derivative represented by the general formula (I) [X is H, a halogen, NO2 , CH, a (halo) 1 to 6C alkyl, a (halo) 1 to 6C alkoxy, a (halo) 1 to 6C alkylthio, (substituted) phenyl, or the like; (n) is 0 to 4; or X may form a condensed ring together with the adjacent C on the benzene ring; R is a (halo) 1 to 8C alkyl, a 1 to 4C alkoxy (1 to 8C) alkyl, a 1 to 4C alkylthio (1 to 8C) alkyl, a 1 to 4C alkylsulfinyl (1 to 8C) alkyl, a phenyl (1 to 4C) alkyl, (substituted) phenyl, a (substituted) aromatic heterocyclic (1 to 4C) alkyl, a (substituted) aromatic heterocyclic group, or the like] comprises reacting a phthalic dihalide of formula (II) or a 3,3-dihalogenophthalide of formula (II') (Hal is a halogen) with an amine compound of formula (III): R-NH2 in the presence of a base in a two phase-based solvent comprising water and an organic solvent.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a method for producing a phthalisoimide derivative represented by the general formula (I), which is useful as a raw material or an intermediate for producing pharmaceuticals, agricultural chemicals and chemicals.

[0002]

2. Description of the Related Art Phthalisoimide derivatives are useful as synthetic intermediates or raw materials for agricultural chemicals, pharmaceuticals and chemicals.
As for pesticides, for example, Japanese Patent Application Laid-Open
-240857 and Japanese Patent Application No. 11-338715.
And compound useful as a raw material compound or an intermediate for agricultural and horticultural insecticides described in Japanese Patent Application Publication No.

With respect to the method for producing phthalisoimides,
Broadly speaking, the following methods have been reported. A method for producing a phthalisoimide derivative by reacting phthalic anhydrides with amines to produce N-substituted phthalamic acid, followed by dehydration condensation using various dehydrating agents. For example, J. Org. Chem. , 1973,3
8, 4164; Med. Chem. , 1967, 1
0,982; Chem. Soc. , Perkin
Trans. 1, 1988, 2149; Org. C
hem. , 1963, 28, 2018; Am. Ch
em. Soc. , 1975, 97, 5582 and JP-A-11-240857. A method for producing a phthalisoimide derivative by reacting phthalic dichlorides with amines. For example, Khim.
Geterotsikl. Soedin. , 1984,
9,1280 etc. A method for producing a phthalisoimide derivative by reacting a 3,3-dichlorophthalide with an amine. For example, Te
Trahedron Letters, 1991, 32
(23), 2637 and the like.

[0004]

However, this method requires a large amount of expensive reagents such as chloroformate, trifluoroacetic anhydride, N, N'-dicyclohexylcarbodiimide as a dehydrating condensing agent, and is suitable for industrialization. Absent. In the above method, since acid chlorides generally considered to be unstable to water are used as a raw material, non-aqueous and expensive triethylamine is used as a base, and bulky two equivalents of triethylamine hydrochloride are precipitated. For,
There is a problem that the amount of the solvent is required to be larger than usual. or,
In the above method, since acetonitrile, which is toxic and may possibly affect the health of manufacturing workers, is used as a solvent, there is a problem in terms of safety and industrialization in terms of equipment. Further, the same problem as described above is involved. In the prior art, various problems, that is, an expensive base and a reagent such as a dehydration condensing agent are required, and a large amount of precipitate is generated, so that production efficiency is reduced.
Alternatively, there has been a problem in industrialization due to the high toxicity of the solvent and the like, and the cost of handling and post-treatment in terms of safety and equipment.

[0005]

Means for Solving the Problems The inventors of the present invention have solved the above-mentioned problems and made intensive studies to develop a novel method for producing phthalisoimides. As a result, phthalic dihalides or 3,3-diphthalates The inventors have found that the above object can be achieved by reacting a halogenophthalide with an amine in a two-phase solvent of water and an organic solvent under basic conditions, thereby completing the present invention.

That is, the present invention provides a compound represented by the general formula (II):

Embedded image (Wherein X may be the same or different and represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a (C ₁ -C ₆ ) alkyl group,
Halo (C ₁ -C ₆ ) alkyl group, (C ₁ -C ₆ ) alkoxy group, halo
(C ₁ -C ₆ ) alkoxy group, (C ₁ -C ₆ ) alkylthio group, halo
(C ₁ -C ₆ ) represents an alkylthio group or a phenyl group which may be substituted, and n represents an integer of 0 to 4. X can form a condensed ring together with an adjacent carbon atom on the benzene ring, and the condensed ring may be the same or different and includes a halogen atom, a (C ₁ -C ₆ ) alkyl group, Halo (C ₁ -C ₆ )
One or more selected from an alkyl group, a (C ₁ -C ₆ ) alkoxy group, a halo (C ₁ -C ₆ ) alkoxy group, a (C ₁ -C ₆ ) alkylthio group and a halo (C ₁ -C ₆ ) alkylthio group May be substituted. Hal represents a halogen atom which may be the same or different. The phthalic acid dihalides represented by the formula) or the general formula (II ′):

[0007]

Embedded image (Wherein X, n and Hal are the same as above) in a two-phase solvent composed of water and an organic solvent in the presence of a base in a two-phase solvent represented by the general formula ( III): R-NH ₂ (III)

(Where R is (C₁-C₈) Alkyl group, halo
(C₁-C₈) Alkyl group, (C₁-C_Four) Alkoxy (C₁-C₈) Al
Kill group, (C₁-C_Four) Alkylthio (C₁-C₈) Alkyl group,
(C₁-C_Four) Alkylsulfinyl (C₁-C₈) Alkyl group, (C
₁-C_Four) Alkylsulfonyl (C₁-C ₈) Alkyl group, (C₁-
C_Four) Alkoxyimino (C₁-C₈) Alkyl group, (C₁-C_FourA)
Alkylaminocarbonyloxy (C₁-C₈) Alkyl group,
(C₁-C_Four) Alkoxycarbonyl (C₁-C₈) Alkyl group, (C₁
-C_Four) Alkoxycarbonylamino (C₁-C₈) Alkyl group,
It may have one or more substituents which may be the same or different.
A phenyl group, one or more of which may be the same or different on the ring
Optionally substituted phenyl (C₁-C_Four) Alkyl group, on ring
May have one or more substituents which may be the same or different.
One or more identical or different aromatic heterocyclic groups or rings
An aromatic heterocyclic ring which may have a good substituent (C₁-C_Four) Al
Represents a kill group. )
General formula (I) characterized by:

[0009]

Embedded image (Wherein, X, n and R are the same as described above).

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION Examples of each substituent in the present invention are shown below. In the shorthand notation of the chemical formula in the present invention,
"I" is "iso", "sec" is "secondary",
“T” means “tertiary”. General formula of the present invention
In the definition of the substituent of the phthalisoimide derivative represented by (I), "halogen atom" is a chlorine atom, a bromine atom,
It represents an iodine atom or a fluorine atom, and “(C ₁ -C ₆ ) alkyl” is, for example, methyl, ethyl, n-propyl, i-
Propyl, n-butyl, i-butyl, s-butyl, t-
A straight-chain or branched alkyl group having 1 to 6 carbon atoms such as butyl, n-pentyl, n-hexyl, etc., which may be the same or different from “halo (C ₁ -C ₆ ) alkyl” It represents a straight-chain or branched alkyl group having 1 to 6 carbon atoms substituted by one or more halogen atoms.

Examples of the aromatic heterocyclic group include furan,
Thiophene, pyrrole, oxazole, oxazoline,
Isoxazole, thiazole, isothiazole, imidazole, pyrazole, 1,2,4-oxadiazole,
1,3,4-oxadiazole, 1,2,4-thiadiazole, 1,3,4-thiadiazole, 1,2,3-thiadiazole, 1,2,5-thiadiazole, 1,2,2
Examples thereof include 3-triazole, 1,2,4-triazole, tetrazole, pyridine, pyrimidine, pyridazine, pyrazine, and triazine, and the nitrogen atom in the molecule may be oxidized. In addition, the benzo derivative may be used, and “benzo derivative” includes, for example, benzofuran, isobenzofuran, 1-benzothiophene, 2-benzothiophene, indole, isoindole, 1,2-benzothiazole, 1,3-benzole Thiazole, 2,1-benzothiazole, indazole, benzimidazole, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, phthalazine, 1,2,3-benzothiadiazole, benzotriazole, benzoxazine, benzothiazine, benzopyridazine, 1-oxo-4 -Azanaphthalene, 1-thia-4-azanaphthalene and the like,
There is no particular limitation on the substitution position.

The method for producing the phthalisoimide derivative represented by the general formula (I) of the present invention is, for example, schematically shown as follows.

Embedded image (In the formula, X, n and R are the same as described above.)

That is, a phthalic acid dihalide represented by the general formula (II) or a 3,3-dihalogenophthalide represented by the general formula (II ') and an amine represented by the general formula (III) Is reacted in a two-phase solvent comprising an organic solvent and water in the presence of a base to produce a phthalisoimide derivative represented by the general formula (I). The amount of the amines represented by the general formula (III) used in this reaction is the amount of the phthalic acid dihalides represented by the general formula (II) or the amount of the 3,3-diamine represented by the general formula (II '). 0.5 to 2 for halogenophthalides
It may be appropriately selected and used from the range of equivalents according to economy, and preferably in the range of 0.9 to 1.1 equivalents.

The base used in the present reaction includes, for example, alkali metal atoms such as sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, etc., and alkaline earth metal atoms. Inorganic bases such as hydroxides or carbonates can be used. The amount of the base used is phthalic dihalides represented by the general formula (II) or 3,3-dihalides represented by the general formula (II ′).
It can be used in a range of 1/2 to an excess amount with respect to the dihalogenophthalides, and preferably in a range of 2 to 2.5 equivalents. The amount of the water solvent used in this reaction is represented by the general formula (II)
1 to 3 g of the 3,3-dihalogenophthalide represented by the general formula (II ') or the phthalic acid dihalide represented by the formula:
It may be appropriately selected and used from the range of 50 ml, and preferably in the range of 5 to 20 ml.

The organic solvent used in the present reaction may be any solvent which does not significantly inhibit the progress of the present reaction and is hardly miscible or soluble in water. Examples of the organic solvent include aromatic hydrocarbons such as benzene, toluene and xylene. Hydrogens, pentane, hexane, heptane, aliphatic hydrocarbons such as nonane, dichloromethane, chloroform, dichloroethane, trichloroethane, dichloropropane, trichloroethylene, tetrachloroethylene, fluorobenzene, chlorobenzene,
Halogenated hydrocarbons such as dichlorobenzene, nitro hydrocarbons such as nitromethane, nitroethane and nitropropane; nitrile hydrocarbons having 3 or more carbon atoms such as propionitrile and butyronitrile; diethyl ether and diisopropyl ether; Ether solvents and ester solvents such as ethyl acetate and butyl acetate can be used. These organic solvents can be used alone or in combination of two or more. The amount of the organic solvent used is phthalic dihalides represented by the general formula (II) or the general formula (I
The amount may be appropriately selected from the range of 0.5 to 50 ml per 1 g of the 3,3-dihalogenophthalide represented by I ′), and is preferably in the range of 1 to 10 ml.

The reaction may be carried out at a temperature in the range of -10 to 100 ° C, preferably in the range of 0 to 20 ° C. The reaction time of this reaction is not fixed depending on the reaction temperature, the reaction scale and the like, but may be selected from a range of several minutes to 48 hours. After completion of the reaction, the phthalisoimide derivative represented by the general formula (I) can be produced by isolating from the reaction system containing the target substance by a conventional method, and purifying as necessary.
Further, after completion of the reaction, the compound can be directly subjected to the next step reaction utilizing the present derivative without isolation.

The phthalic acid dichlorides represented by the general formula (II), which is a raw material for this reaction, or the phthalic acid dichloride represented by the general formula (II ')
The 3-dihalogenophthalides can be produced from the corresponding phthalic anhydrides by a known method.
rgnic Syntheses Coll. vo
l. 2,528. Further, as another method for producing the phthalic dihalides represented by the general formula (II), for example, J. Pharm. Org. Chem. ,
1973, 38, 2557 and the like. As another method for producing 3,3-dihalogenophthalides represented by the general formula (II), for example, Indian J. Chem. Chem. , Sec
t. B, 1980, 1913 (6), 473.

[0018]

The following are typical examples and reference examples of the present invention, but the present invention is not limited to these examples. Embodiment 1 FIG. Production of N- (1,1-dimethyl-2-methylthioethyl) phthalisoimide (when phthalic acid dichloride is used as a raw material). In a 50 ml glass reactor, sodium hydroxide 0.40
g (0.01 mol) in 10 ml of water was added, and 5 ml of dichloroethane and 1,1-dimethyl-
After adding 0.59 g (4.9 mmol) of 2-methylthioethylamine, 1.0 g (4.9 mmol) of phthalic dichloride was added dropwise at 20 ° C. or lower under ice cooling. After stirring at room temperature for 30 minutes, the organic layer was separated, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 1.18 g (yield: 97%) of the desired product. ¹ H-NMR (δ value, ppm / DMSO-d ₆ ) 1.53 (s.6H), 2.24 (s.3H), 2.89 (s.2H), 7.65-7.80 (m.2
H), 7.87-7.93 (m, 2H).

Embodiment 2 FIG. N- (1,1-dimethyl-2-
Production of (methylthioethyl) phthalisoimide (3,3-
When dichlorophthalide is used as a raw material). In a 50 ml glass reactor, 0.40 sodium hydroxide was added.
g (0.01 mol) in 10 ml of water was added, and 5 ml of dichloroethane and 1,1-dimethyl-
After adding 0.59 g (4.9 mmol) of 2-methylthioethylamine, 1.0 g (4.9 mmol) of 3,3-dichlorophthalide was added dropwise at 20 ° C. or lower under ice cooling. After stirring at room temperature for 30 minutes, the organic layer was separated, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.15 g (yield 94%) of the desired product.

Embodiment 3 FIG. N- (1,1-dimethyl-2-
Preparation of (methylthioethyl) -7-chlorophthalisoimide. 0.35% sodium hydroxide in a 50 ml glass reactor
g (8.6 mmol) in 10 ml of water was added, and 5 ml of dichloroethane and 1,1-dimethyl-
After adding 0.51 g (4.2 mmol) of 2-methylthioethylamine, a solution of 1.0 g (4.2 mmol) of 3-chlorophthalic dichloride in 2 ml of dichloroethane was added dropwise at 20 ° C. or lower under ice-cooling. After stirring at room temperature for 30 minutes, the organic layer was separated, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.15 of the desired product.
g (yield 97%) was obtained. ¹ H-NMR (δ value, ppm / DMSO-d ₆ ) 1.52 (s.6H), 2.23 (s.3H), 2.89 (s.2H), 7.6-7.7 (m, 2H),
7.83 (d, 1H).

Embodiment 4 FIG. Production of N- (4-heptafluoroisopropyl-2-methylphenyl) -7-bromophthalisoimide 0.42 sodium hydroxide in a 50 ml glass reactor
g (10 mmol) in 10 ml of water was added, and 5 ml of dichloroethane and 0.58 g of 4-heptafluoroisopropyl-2-methylaniline (2.1
Then, a solution of 1.0 g (3.5 mmol) of 3-bromophthalic acid dichloride in 2 ml of dichloroethane was added dropwise at room temperature. After stirring for 30 minutes, the organic layer was separated, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained concentrate was crystallized from hexane to obtain 0.87 g of the desired product (yield). 86%). ¹ H-NMR (δ value, ppm / DMSO-d ₆ ) 2.34 (s.3H), 7.25 (dd.1H), 7.45 (d.1H), 7.47 (s.1H), 7.
72 (t.1H), 7.94 (d.1H), 8.09 (d.1H).

Embodiment 5 FIG. Production of N- (2-methyl-4-trifluoromethoxyphenyl) -7-bromophthalisoimide. 0.42 sodium hydroxide in a 50 ml glass reactor
g (10 mmol) in 10 ml of water was added, and 5 ml of dichloroethane and 0.61 g (3.2 mmol) of 2-methyl-4-trifluoromethoxyaniline were further added. 1.0 g (3.5 mmol) of dichloride in dichloroethane (2 m
l) The solution was added dropwise. After stirring for 30 minutes, the organic layer was separated, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained concentrate was crystallized from hexane to give 1.09 g of the desired product (yield). 85%). ¹ H-NMR (δ value, ppm / DMSO-d ₆ ) 2.34 (s.3H), 7.08 (d.1H), 7.11 (s.1H), 7.29 (d.1H), 7.
70 (t.1H), 7.91 (d.1H), 8.07 (d.1H).

Embodiment 6 FIG. Production of N- (2-methyl-4-trifluoromethoxyphenyl) -7-iodophthalisoimide In a 50 ml glass reactor, sodium hydroxide 0.36 was added.
g (9 mmol) in 10 ml of water is added,
Further 5 ml of dichloroethane and 0.57 g (3.0 mmol) of 2-methyl-4-trifluoromethoxyaniline
After addition of 1.0 g (3.0 mmol) of 3-iodophthalic acid dichloride at room temperature in dichloroethane (2 m
l) The solution was added dropwise. After stirring for 30 minutes, the organic layer was separated, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 82%). ¹ H-NMR (δ value, ppm / DMSO-d ₆ ) 2.33 (s.3H), 7.08 (d.1H), 7.10 (s.1H), 7.28 (d.1H), 7.
51 (t.1H), 8.09 (d.1H), 8.19 (d.1H).

Embodiment 7 FIG. N- (1,1-dimethyl-2-
Preparation of (methylthioethyl) -7-iodophthalisoimide. Sodium hydroxide 0.12 in a 20 ml glass reactor
g (3 mmol) dissolved in 3 ml of water was added, and 2 ml of dichloroethane and 0.12 g (1.0 mmol) of 1,1-dimethyl-2-methylthioethylamine were further added. Dichloride,
Mixture of 3,3-dichloro-7-iodophthalide and 3,3-dichloro-4-iodophthalide (1: 1: 1)
0.33 g (1.0 mmol) of dichloroethane (2 m
l) The solution was added dropwise. After stirring for 60 minutes, the organic layer was separated, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The resulting concentrate was crystallized from hexane to obtain 0.30 g of the desired product (yield). 80%). ¹ H-NMR (δ value, ppm / DMSO-d ₆ ) 1.56 (s.6H), 2.13 (brs.3H), 2.95 (brs.2H), 7.45 (t.1
H), 8.13 (d.1H), 8.14 (d.1H).

Reference Example 1 N ^1- (2-methyl-4-trifluoromethoxyphenyl) -N ^2- (1-methylethyl)
Production of -3-iodophthalic acid diamide (hereinafter referred to as "reference compound"). 1.0 g (2.2 mmol) of N- (2-methyl-4-trifluoromethoxyphenyl) -7-iodophthalisoimide (the compound of Example 7) was added to acetonitrile 10
and isopropylamine 0.15 g was added to the solution.
(2.5 mmol) was added and the reaction was carried out at room temperature for 1 hour. After completion of the reaction, the precipitated crystals were collected by filtration to obtain 0.90 g (yield 81%) of the desired product. Physical properties: m. p. 219-220 ° C

Reference Example 2 Diamondback moth (Plutella xylostella)
Insecticidal test against. The adults of Chinese moth were released to the seedlings of Chinese cabbage to lay eggs, and the seedlings of Chinese cabbage with laying eggs were immersed for 30 seconds in a drug solution obtained by diluting a drug containing a reference compound as an active ingredient to 500 ppm two days after release. After air-drying, it was left still in a constant temperature room at 25 ° C.
Six days after immersion in the drug solution, the number of hatching larvae was examined, the mortality was calculated by the following formula, and the judgment was made according to the following criteria. 1
Ward three consecutive system. As a result, the reference compound showed 100% mortality.

Reference Example 3 Spodoptera li
tura) against insects. Cabbage leaf pieces (variety: four seasons harvest) are immersed for about 30 seconds in a drug solution in which a drug containing a reference compound as an active ingredient is diluted to 500 ppm. After inoculation, it was left still in a constant temperature room at 25 ° C. and 70% humidity. 10 units per ward in three districts. As a result, Reference Compound 1 showed 100% mortality.

[0028]

According to the production method of the present invention, phthalisoimides can be produced safely in a simple and short process with almost no by-products. Further, the phthalisoimides can be produced industrially advantageously, such as being able to supply inexpensive and high-quality products.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C07C 255/57 C07C 255/57 // C07B 61/00 300 C07B 61/00 300 (72) Inventor Arai Ino Nobuyuki 765-3-203, Mukono-cho, Kawachinagano-shi, Osaka (72) Inventor Hironori Kodama 685-7, Pottery Kita, Sakai-shi, Osaka (72) Inventor Kazuhiro Takagi 4-12-10-, Kitahorie, Nishi-ku, Osaka-shi, Osaka 1124 (72) Inventor Akira Seo 2-3-19 Kimigaoka, Hashimoto City, Wakayama Prefecture F-term (reference) 4C037 RA20 4H006 AA01 AB84 4H039 CA42 CA71 CD10 CD20 CH40

Claims (5)

[Claims] 1. A compound of the general formula (II):(Wherein X may be the same or different, and a hydrogen atom, a halo
Gen atom, nitro group, cyano group, (C₁-C₆) Alkyl group,
Halo (C₁-C₆) Alkyl group, (C₁-C₆) Alkoxy group, halo
 (C₁-C₆) Alkoxy group, (C₁-C₆) Alkylthio group, halo
 (C₁-C₆) Alkylthio group or an optionally substituted
And n represents an integer of 0 to 4. Also, X is
Together with the adjacent carbon atom on the fused ring
And the condensed rings may be the same or different.
, Halogen atom, (C₁-C₆) Alkyl group, halo (C₁-C₆)
Alkyl group, (C₁-C₆) Alkoxy group, halo (C₁-C₆) Al
Coxy group, (C₁-C₆) Alkylthio or halo (C₁-C₆A)
Having one or more substituents selected from alkylthio groups.
Can also be. Hal is the same or different halogen
Indicates an atom. A) phthalic acid dihalides represented by
General formula (II '):(In the formula, X, n and Hal are the same as described above.)
3,3-Dihalogenophthalides are separated from water and organic solvents.
In a two-phase solvent, a compound of the formula (III): R-NH_Two (III) (where R is (C₁-C₈) Alkyl group, halo (C₁-C₈) Archi
Group, (C₁-C_Four) Alkoxy (C₁-C₈) Alkyl group, (C₁-C
_Four) Alkylthio (C₁-C₈) Alkyl group, (C₁-C_Four) Alkyl
Sulfinyl (C₁-C₈) Alkyl group, (C₁-C_Four) Alkyls
Ruphonyl (C₁-C ₈) Alkyl group, (C₁-C_Four) Alkoxyimi
No (C₁-C₈) Alkyl group, (C₁-C_Four) Alkylaminocarbo
Nyloxy (C₁-C₈) Alkyl group, (C₁-C_Four) Alkoxyka
Rubonil (C₁-C₈) Alkyl group, (C₁-C_Four) Alkoxycar
Bonylamino (C₁-C₈) Alkyl group, one or more same or different
A phenyl group, which may have a substituent,
It may have one or more substituents which may be the same or different.
Phenyl (C₁-C_Four) Alkyl groups, one or more identical or
An aromatic heterocyclic group which may have a different substituent,
Has at least one substituent which may be the same or different on the ring
Aromatic heterocycle (C₁-C_Four) Represents an alkyl group. )so
General reaction characterized by reacting with amines represented
Formula (I):(Wherein, X, n and R are the same as described above)
A method for producing a luisoimide derivative. 2. The reaction of a phthalic dihalide represented by the general formula (II) with an amine represented by the general formula (III) in a two-phase mixed solvent of water and an organic solvent. The method for producing the phthalisoimide derivative according to the above. 3. The method for producing a phthalisoimide derivative according to claim 2, wherein the phthalic dihalides are phthalic dichlorides. 4. A three-phase mixed solvent of water and an organic solvent comprising a 3,3-dihalogenophthalide represented by the general formula (II ′) and an amine represented by the general formula (III). The method for producing a phthalisoimide derivative according to claim 1, wherein 5. The method according to claim 3, wherein the 3,3-dihalogenophthalide is 3,3.
The method for producing a phthalisoimide derivative according to claim 4, which is a dichlorophthalide.