JPH03217459A - Production of imide compound - Google Patents
Production of imide compoundInfo
- Publication number
- JPH03217459A JPH03217459A JP2011804A JP1180490A JPH03217459A JP H03217459 A JPH03217459 A JP H03217459A JP 2011804 A JP2011804 A JP 2011804A JP 1180490 A JP1180490 A JP 1180490A JP H03217459 A JPH03217459 A JP H03217459A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- substituted
- dicarboxylic acid
- groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B25/00—Quinophthalones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、顔料、染料、カラー液晶用および偏光板用材
料として用いられるイミド型の黄色系の二色性色素の新
規な製造法に関するものである。[Detailed Description of the Invention] [Field of Industrial Application] The present invention relates to a novel method for producing imide-type yellow dichroic dyes used as pigments, dyes, and materials for color liquid crystals and polarizing plates. It is.
従来、一般式（Ｉ）のような黄色系のキノフタロン系色
素が知られているが、これは、例えばその原料として、
弐（Ｖ）
で示されるキノフタロンージカルボン酸、あるいはその
酸無水物である弐（’ｖＴ）
で示される化合物と、
弐（Ｉ［Ｉ）
Ｒ−ＮＨ２ （ＩＩＩ）
（式（ＩＩＩ）中、Ｒは置換または無置換アルキル基、
アリール基、複素環基を表わす。）
で示される化合物を加熱反応することにより得ることが
できる（特開昭５２−１０３４１、特開昭５２− １０
３４２、特開昭６２−２７０６６４ ＞。Hitherto, yellow quinophthalone dyes such as those represented by general formula (I) have been known; for example, as raw materials thereof,
Quinophthalone-dicarboxylic acid represented by 2 (V) or its acid anhydride, a compound represented by 2 ('vT), and 2 (I[I) R-NH2 (III)
(In formula (III), R is a substituted or unsubstituted alkyl group,
Represents an aryl group or a heterocyclic group. ) can be obtained by thermally reacting the compound represented by (JP-A-52-10341, JP-A-52-10)
342, JP-A-62-270664>.
この場合、酸無水物（■）は、大気中の水分で容易に分
解して、ジカルボン酸（Ｖ）式との混合物となっている
。In this case, the acid anhydride (■) is easily decomposed by moisture in the atmosphere and becomes a mixture with the dicarboxylic acid (V).
しかるに、従来の方法では、式（Ｖ）で示されるジカル
ボン酸と式（ＩＩＩ）で示されるアミンよりイミドを選
択的に合成することは出来ず、前記特開昭に記載される
方法では、純度よく、目的のイミド化合吻を得ることは
できなかった。However, with conventional methods, it is not possible to selectively synthesize an imide from the dicarboxylic acid represented by formula (V) and the amine represented by formula (III), and the method described in JP-A-Sho, Unfortunately, we were unable to obtain the desired imidized proboscis.
そのため、弐（Ｖ）又は式（■）を中間体として製造し
た式（１）の化合物を樹脂に混合した時は透明の樹脂成
型物が得られない。又、液晶用色性色素あるいは偏光板
用二色性色素とした時は、不純物により二色比が著しく
低下するという欠点があり、工業的には採用出来る方法
ではなかった。Therefore, when a compound of formula (1) produced using 2 (V) or formula (■) as an intermediate is mixed with a resin, a transparent resin molded product cannot be obtained. Furthermore, when used as a chromatic dye for liquid crystals or a dichroic dye for polarizing plates, there is a drawback that the dichroic ratio is significantly lowered due to impurities, and this method cannot be adopted industrially.
本発明の目的は、キノフタロンージカルボン酸系の中間
体を原料として、純度よく、目的の二色性色素イミド化
合物を得る製造方法を提供するところにある。An object of the present invention is to provide a method for producing a desired dichroic dye imide compound with high purity using a quinophthalone-dicarboxylic acid intermediate as a raw material.
本発明は、一般式（１）
（弐四）中、Ｘはハロゲン原子、メチル基、トキシ基を
表わし、ｎは０または１を表わし、は置換または無置換
アルキル基、アリール基、素環基を表わす。）
で示される化合物を製造するに際して、一般式（ＩＩ）
メ
Ｒ
複
（式（ＩＩ）中、Ｘ，ｎは式（１）のＸ，ｎと同一の意
味を表わす。）
で示されるジカルボン酸と
一限式（Ｉ［［）
Ｒ−ＮＨ２ （Ｉ［［）（式（ＩＩ
Ｉ）中、Ｒは式（１）中のＲと同一の意味を表わす。）
で示されるアミンを一般式（ＩＶ）
Ｙ’ Ｙ２
（式（ＩＶ）中、Ｙ１、Ｙ２、Ｙ３、Ｙ４、ＹＳは水素
原子、置換または無置換のアルキル基、置換または無置
換のアルコキシ基、置換または無置換のアルコキンカル
ボニル基、ハロゲン原子を表わす。）
で示されるフェノール誘導体を溶媒として加熱反応させ
ることを特徴とする式（１）で表わされる化合物を製造
方法である。In the present invention, in the general formula (1) (24), X represents a halogen atom, a methyl group, or a toxy group, n represents 0 or 1, and is a substituted or unsubstituted alkyl group, aryl group, or a ring group. represents. ) When producing the compound represented by the general formula (II), a dicarboxylic acid represented by the formula (II) and one-limited formula (I[[) R-NH2 (I[[) (formula (II
In I), R has the same meaning as R in formula (1). ) The amine represented by the general formula (IV) Y' Y2 (In the formula (IV), Y1, Y2, Y3, Y4, YS are hydrogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkoxy groups, This is a method for producing a compound represented by formula (1), which is characterized by carrying out a heating reaction using a phenol derivative represented by (representing a substituted or unsubstituted alkoxycarbonyl group or a halogen atom) as a solvent.
式（ＩＩ）中、Ｘで表わされるキノリン環に置喚しても
よいハロゲン原子はフ／素、塩素、臭素、ヨウ素が挙げ
られる。In formula (II), examples of the halogen atom which may be substituted on the quinoline ring represented by X include fluorine, chlorine, bromine, and iodine.
式（Ｉ［ｌ）中、Ｒで示される置換または無置換のアル
キル基の例としては、炭素数１〜２０の直鎖又は分岐の
炭化水素基：メトキシメチル基、エトキシメチル基、メ
トキシエチル基、エトキシエチル基、プロポキシエチル
基、メトキシブチル基、フエノキシエチル基なとの直鎖
又は分岐の総炭素数１〜３０のアルコキシアルキル基：
クロルメチル基、クロルエチル基、クロルブチル基、フ
ロ口メチル基、フロロエチル基、プロムメチル基、プロ
ムエチル基、プロムブチル基、ヨウ化メチル基、ヨウ化
エチル基、ヨウ化ブチル基などの炭素数１〜２０のハロ
ゲノアルキル基：トリフロ口メチル基、トリク０コメチ
ル基、ジブロムメチル基、ペンタフロロエチル基、ヘプ
タフ口口プロビル基なトノバーハロゲノアルキル基：ヘ
ンジル基、フェニルエチル基などのアラルキル基などが
挙げられる。In formula (I[l), examples of the substituted or unsubstituted alkyl group represented by R include straight chain or branched hydrocarbon groups having 1 to 20 carbon atoms: methoxymethyl group, ethoxymethyl group, methoxyethyl group; , an ethoxyethyl group, a propoxyethyl group, a methoxybutyl group, a phenoxyethyl group, and a straight chain or branched alkoxyalkyl group having a total of 1 to 30 carbon atoms:
Halogenoalkyl having 1 to 20 carbon atoms such as chloromethyl group, chloroethyl group, chlorobutyl group, fluoromethyl group, fluoroethyl group, prommethyl group, promoethyl group, prombutyl group, methyl iodide group, ethyl iodide group, butyl iodide group Groups: trifluoromethyl group, tricomethyl group, dibromomethyl group, pentafluoroethyl group, heptafluoropropyl group; Tonovahalogenoalkyl group: aralkyl groups such as henzyl group and phenylethyl group.
置換または無置換のアリール基の例としては、下記一般
式（■）、（■）、（ＩＸ）、（Ｘ）および（ＸＩ）
で示される基が挙げられる。Examples of substituted or unsubstituted aryl groups include groups represented by the following general formulas (■), (■), (IX), (X) and (XI).
式（■）〜（ＸＩ）において、各芳香族環α、β、γ、
δ、ε、ζ、η、θ、乙およびκは、ハロゲン原子；メ
チル基、エチル基、イソプロビル基などの直鎖又は分岐
又は環状の総炭素数１〜４の炭化水素基，メトキソ基、
エトキン基、プロポキン基などの直鎮又は分岐の総炭素
数１〜６のアルコキソ基などで置換されてもよい。又、
Ａは水素原子：ハロゲン原子；メチル基、エチル基、シ
クロヘキシル基などの直鎖又は分岐又は環状の総炭素数
１〜２０の炭化水素基；メトキシ基、エトキン基、フェ
ニルメトキシ基なとの直鎖または分岐の総炭素数１〜３
０のアルコキシ基；フェノキシ基などの総炭素数１〜２
２のアリールオキシ基あるいは、下記一般弐（ＸＩ）、
（ＸＩＩＩ）、（ＸＩＶ）、（ＸＶ）および（Ｘ■）で
表わされる置換基を示す。In formulas (■) to (XI), each aromatic ring α, β, γ,
δ, ε, ζ, η, θ, O and κ are halogen atoms; straight chain, branched or cyclic hydrocarbon groups having a total of 1 to 4 carbon atoms such as methyl group, ethyl group, isoprobyl group, methoxo group,
It may be substituted with a straight or branched alkoxo group having 1 to 6 carbon atoms in total, such as an etochyne group or a propochyne group. or,
A is a hydrogen atom: a halogen atom; a straight chain, branched or cyclic hydrocarbon group having a total of 1 to 20 carbon atoms such as a methyl group, ethyl group, or cyclohexyl group; a straight chain such as a methoxy group, an ethquin group, or a phenylmethoxy group Or total carbon number of branches 1-3
0 alkoxy group; total carbon number 1-2 such as phenoxy group
2 aryloxy group or the following general 2 (XI),
The substituents represented by (XIII), (XIV), (XV) and (X■) are shown.
Ｏ
（式（Ｘｌｌ）〜（ＸＶＩ）のＺは水素原子；ハロゲン
原子；メチル基、エチル基、プロビル基、ブチル基など
の分岐又は直鎖の総炭素数１〜２０の炭化水素基；メト
キシ基、エトキシ基、プロボキシ基、ブトキシ基など分
岐又は直鎖の総炭素数１〜１０のアルコキシ基；フェニ
ル基、ナフチル基などの了りール基；フェノキシ基など
の総炭素数１〜１４のアリールオキシ基；アセトキシ基
などのカルボキシ基；クロロメチル基、クロロエチル基
などの炭素数１〜２のハロゲノアルキル基；トリフロロ
メチル基などのバーハロゲノアルキル基；ヘンジル基、
フエニルエチル基などの総炭素数１〜２０のアラルキル
基を示す。O (Z in formulas (Xll) to (XVI) is a hydrogen atom; a halogen atom; a branched or straight-chain hydrocarbon group having a total of 1 to 20 carbon atoms such as a methyl group, an ethyl group, a proyl group, a butyl group; a methoxy group Branched or linear alkoxy groups having a total of 1 to 10 carbon atoms such as , ethoxy, propoxy, and butoxy groups; Ryaryl groups such as phenyl and naphthyl groups; Aryloxy having 1 to 14 total carbon atoms such as phenoxy groups Group; Carboxy group such as acetoxy group; Halogenoalkyl group having 1 to 2 carbon atoms such as chloromethyl group and chloroethyl group; Barhalogenoalkyl group such as trifluoromethyl group; Henzyl group,
It represents an aralkyl group having a total of 1 to 20 carbon atoms, such as a phenylethyl group.
置換または無置換の複素環基の例としては、チオフエン
、オキサゾール、ヘンゾオキサヅール、チアゾール、ヘ
ンゾチアゾール、フラン、ピロル、キノリン、ピリジン
、メチルピリジンなどの置換又は無置換の複素環基が挙
げられる。Examples of substituted or unsubstituted heterocyclic groups include substituted or unsubstituted heterocyclic groups such as thiophene, oxazole, henzoxadur, thiazole, henzothiazole, furan, pyrrol, quinoline, pyridine, and methylpyridine. .
弐（１）で示されるイミド化合物を製造するに際して、
使用する溶媒は、式（■）
（弐（ＴＶ）中、Ｙ１、Ｙ２、Ｙ３、Ｙ４、Ｙ５は水素
原子、置換または無置換のアルキル基、置換または無置
換のアルコキシ基、置換または無置換のアルコキシカル
ボニル基、ハロゲン原子を表わす。）
で示されるフェノール誘導体である。When producing the imide compound represented by (1),
The solvent used is of the formula (■) (In (TV), Y1, Y2, Y3, Y4, Y5 are hydrogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted (represents an alkoxycarbonyl group or a halogen atom).
式（ＴＶ）中、置換または無置換のアルキル基の例とし
ては、メチル基、エチル基、プロビル基、ブチル基など
の直鎖又は分岐の総炭素数１〜４の炭化水素基；クロル
メチル基、クロルエチル基、フロルメチル基、フロルエ
チル基、プロムメチル基、プロムエチル基、ヨウ化メチ
ル基、ヨウ化エチル基などの炭素数１〜２のハロゲノア
ルキル基；トリフロロメチル基、トリクロロメチル基、
ジブロムメチル基、ペンタクロ口エチル基などのパーハ
ロゲノアルキル基；ヘンジル基などのアラルキル基など
が挙げられる。In formula (TV), examples of substituted or unsubstituted alkyl groups include straight chain or branched hydrocarbon groups having a total of 1 to 4 carbon atoms such as methyl group, ethyl group, probyl group, butyl group; chloromethyl group; Halogenoalkyl groups having 1 to 2 carbon atoms such as chloroethyl group, fluoromethyl group, fluoroethyl group, prommethyl group, promoethyl group, methyl iodide group, ethyl iodide group; trifluoromethyl group, trichloromethyl group,
Perhalogenoalkyl groups such as dibromomethyl group and pentacroethyl group; aralkyl groups such as Henzil group, and the like.
置換または無置換のアルコキシ基の例としては、メトキ
シ基、エトキシ基、ブロボキシ基のような炭素数１〜３
の分岐又は直鎖の炭化水素オキシ基；クロロメトキシ基
のようなハロゲノアルコキシ基などが挙げられる。Examples of substituted or unsubstituted alkoxy groups include those having 1 to 3 carbon atoms, such as methoxy, ethoxy, and broboxy groups.
branched or straight-chain hydrocarbon oxy groups; halogenoalkoxy groups such as chloromethoxy groups, and the like.
置換又は無置換のアルコキシ力ルポニル基の例としては
、メトキシカルボニル基、エトキシカルポニル基、プロ
ボキシカルポニル基、ブトキシ力ルボニル基のような炭
素数１〜４の分岐又は直鎖の炭化水素オキシカルボニル
基；クロロメトキシカルボニル基のようなハロゲノアル
コキシカルポニル基などが挙げられる。Examples of substituted or unsubstituted alkoxycarbonyl groups include branched or straight-chain hydrocarbonoxycarbonyl groups having 1 to 4 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, and butoxycarbonyl groups; ; Examples include halogenoalkoxycarbonyl groups such as chloromethoxycarbonyl groups.
ハロゲン原子の例としては、フノ素、塩素、臭素、ヨウ
素が挙げられる。Examples of halogen atoms include fluorine, chlorine, bromine, and iodine.
使用する溶媒の量は、前述の弐（ＩＩ）で示されるジカ
ルボン酸１重量部に対して１〜１００重量部であり、工
業的には５〜２０重量部が好ましい。The amount of the solvent used is 1 to 100 parts by weight, industrially preferably 5 to 20 parts by weight, per 1 part by weight of the dicarboxylic acid represented by II (II).
式（１）で示されるイミド化合物を製造するに際して、
溶媒を加熱する温度は５０〜２００゜Ｃであり、工業的
には１００〜１７０゜Ｃが好ましい。又、式（ＩＩ）で
表わされるジカルポン酸と弐（Ｉ［ｌ）で表わされるア
ミンはほぼ当モル使用する。さらに、必要に応じてキノ
リン、イソキノリン、ビリジンなどの触媒を添加しても
よい。When producing the imide compound represented by formula (1),
The temperature at which the solvent is heated is 50 to 200°C, and industrially preferably 100 to 170°C. Further, the dicarboxylic acid represented by formula (II) and the amine represented by 2 (I[l) are used in approximately equimolar amounts. Furthermore, a catalyst such as quinoline, isoquinoline, or pyridine may be added as necessary.
以下、本発明を実施例により詳しく説明するが、本発明
の範囲はこれらの実施例に限定されるものでないことは
いうまでもない。EXAMPLES Hereinafter, the present invention will be explained in detail with reference to Examples, but it goes without saying that the scope of the present invention is not limited to these Examples.
（実施例〕
実施例１
３゜−ヒドロキシキノフタロン−５，６−ジカルボン酸
３７７重量部と４−アミノー４゜−（５−メチルヘンゾ
オキサゾリル）ビフェニル３０１重量部をイソキノリン
１３０重量部、メタクレゾール３６００重量部中で１５
０゜Ｃに加熱して反応させ、析出した結晶を濾過温度１
００゜Ｃにて濾別し、メタクレゾール７２０重量部、メ
タノール６０００重量部で洗浄、乾燥した。(Example) Example 1 377 parts by weight of 3°-hydroxyquinophthalone-5,6-dicarboxylic acid and 301 parts by weight of 4-amino-4°-(5-methylhenzooxazolyl)biphenyl were mixed with 130 parts by weight of isoquinoline and metacresol. 15 in 3600 parts by weight
Heating to 0°C to react, precipitated crystals were filtered at 1
The mixture was filtered at 00°C, washed with 720 parts by weight of metacresol and 6,000 parts by weight of methanol, and dried.
こうして得られた化合物を（甲）とする。The compound thus obtained is designated as (A).
また、３゜−ヒドロキシキノフタロン−５．６一ジカル
ポン酸無水物を原料として特開昭６２−２７０６６４に
記載された製造法、すなわちＮ−メチルピロリドンを溶
媒として加熱還流する方法を用いて得られるイミド化合
物（下式（Ｘ■））
と前記化合物（甲）の赤外線吸収スペクトルの比較を行
った結果、双方のスペクトルピーク値が一致することを
確認した（表１）。In addition, an imide obtained by using 3°-hydroxyquinophthalone-5.6 monodicarboxylic acid anhydride as a raw material using the production method described in JP-A No. 62-270664, that is, the method of heating under reflux using N-methylpyrrolidone as a solvent. As a result of comparing the infrared absorption spectra of the compound (formula (X■) below) and the compound (A), it was confirmed that the spectral peak values of both were the same (Table 1).
赤外線吸収スペクトルピーク１７８０ｃｍ−’はイミド
基の吸収を示している。The infrared absorption spectrum peak at 1780 cm-' indicates absorption of imide groups.
また、表２に示すように化合物（甲）の元素分析値は化
合物
（Ｘ〜１）
の計算値とよく一致してい
る。Furthermore, as shown in Table 2, the elemental analysis values of compound (A) are in good agreement with the calculated values of compounds (X-1).
表２ 元素分析値
表１および表２の結果より、化合物（甲）は、弐（Ｘ■
）のイミド化合物であることを確認した。Table 2 Elemental analysis values From the results of Tables 1 and 2, compound (A) is
) was confirmed to be an imide compound.
なお、化合物（甲）の収率は９５％、液体クロマトグラ
フによる純度は９８％であった。The yield of compound (A) was 95%, and the purity as determined by liquid chromatography was 98%.
実施例２
３゛−ヒドロキシ−６゛−ブロモキノフタロン５，６−
ジカルボン酸４５６重量部と４−アミノ（４゛−ヘンヅ
チアヅリル）ビフェニル３０１重量部をイソキノリン１
３０重量部、０−クロルフェノール９０００重量部中で
１６０゜Ｃに加熱して反応させ、析出した結晶をｉＩ！
過温度１３０゜Ｃにて濾別し、０−クロロフェノール９
００重量部、メタノール７０００重量部で洗浄、乾燥し
、弐（Ｘ■）の化合物を得た。Example 2 3′-hydroxy-6′-bromoquinophthalone 5,6-
456 parts by weight of dicarboxylic acid and 301 parts by weight of 4-amino(4'-henzthiaduryl)biphenyl were added to 1 part by weight of isoquinoline.
30 parts by weight of 0-chlorophenol and 9000 parts by weight of 0-chlorophenol were heated to 160°C to react, and the precipitated crystals were converted into iI!
Filtered at a supertemperature of 130°C to remove 0-chlorophenol 9.
The product was washed with 00 parts by weight and 7000 parts by weight of methanol, and dried to obtain compound 2 (X■).
得られた化合物の元素分析値を表３に示す。Table 3 shows the elemental analysis values of the obtained compound.
表３ 元素分析値
また、式（Ｘ■）の化合物の収率は９４％、純度は９８
％であった。Table 3 Elemental analysis values The yield of the compound of formula (X■) is 94% and the purity is 98%.
%Met.
実施例３〜９
表４に示すモノ置換アミンと下記一般式（ＶＩＸ）のジ
カルボン酸誘導体を用いて、各種溶剤中で反応を行い、
相当する弐（１）のイミド化合物を得た。Examples 3 to 9 Reactions were carried out in various solvents using the monosubstituted amines shown in Table 4 and dicarboxylic acid derivatives of the following general formula (VIX),
The corresponding imide compound 2 (1) was obtained.
イミト化反応物の確認は、元素分析で行った。The imitization reaction product was confirmed by elemental analysis.
その結果を表５に示す。The results are shown in Table 5.
表５
元素分析値
（発明の効果〕
本発明の方法は、キノフタロン系ジカルボン酸を原料と
してイミド化合物を合成し、かつ、従来の方法で製造し
た二色性色素以上の高純度色素を得ることが出来る点に
おいて優れた製造方法である。Table 5 Elemental analysis values (effects of the invention) The method of the present invention synthesizes an imide compound using quinophthalone dicarboxylic acid as a raw material, and it is possible to obtain a pigment with a higher purity than dichroic pigments produced by conventional methods. This is an excellent manufacturing method in that it can be done.
Claims (1)
シ基を表わし、ｎは０または１を表わし、Ｒは置換また
は無置換アルキル基、アリール基、複素環基を表わす。 ） で示される化合物を製造するに際して、 一般式（II） ▲数式、化学式、表等があります▼（II） （式（II）中、Ｘ、ｎは式（ I ）のＸ、ｎと同一の意
味を表わす。） で示されるジカルボン酸と 一般式（III） Ｒ−ＮＨ＿２（III） （式（III）中、Ｒは式（ I ）中のＲと同一の意味を表
わす。） で示されるアミンを一般式（IV） ▲数式、化学式、表等があります▼（IV） （式（IV）中、Ｙ＾１、Ｙ＾２、Ｙ＾３、Ｙ＾４、Ｙ＾
５は水素原子、置換または無置換のアルキル基、置換ま
たは無置換のアルコキシ基、置換または無置換のアルコ
キシカルボニル基、ハロゲン原子を表わす。） で示されるフェノール誘導体を溶媒として加熱反応させ
ることを特徴とする式（ I ）で表わされる化合物の製
造方法 ２）加熱温度が５０〜２００℃である請求項１記載の製
造方法。[Claims] 1) General formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (I) (In formula (I), X represents a halogen atom, methyl group, or methoxy group, and n is 0 or 1 and R represents a substituted or unsubstituted alkyl group, aryl group, or heterocyclic group. (In formula (II), X and n represent the same meanings as X and n in formula (I).) Dicarboxylic acid represented by the general formula (III) R-NH_2(III) (in formula (III) , R represents the same meaning as R in formula (I).) The amine represented by general formula (IV) ▲There are numerical formulas, chemical formulas, tables, etc.▼(IV) (In formula (IV), Y^ 1, Y^2, Y^3, Y^4, Y^
5 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkoxycarbonyl group, or a halogen atom. 2) A method for producing a compound represented by formula (I), characterized in that the reaction is carried out by heating using a phenol derivative represented by (2) as a solvent.2) The method for producing a compound represented by formula (I) according to claim 1, wherein the heating temperature is 50 to 200C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011804A JP2854908B2 (en) | 1990-01-23 | 1990-01-23 | Method for producing imide compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011804A JP2854908B2 (en) | 1990-01-23 | 1990-01-23 | Method for producing imide compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03217459A true JPH03217459A (en) | 1991-09-25 |
| JP2854908B2 JP2854908B2 (en) | 1999-02-10 |
Family
ID=11788038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011804A Expired - Fee Related JP2854908B2 (en) | 1990-01-23 | 1990-01-23 | Method for producing imide compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2854908B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0669379A1 (en) * | 1994-02-25 | 1995-08-30 | MITSUI TOATSU CHEMICALS, Inc. | Quinophtalone compounds and polarizing films using same |
| WO2003086377A1 (en) * | 2002-04-18 | 2003-10-23 | Institute Of Medicinal Molecular Design. Inc. | Amide derivatives |
| CN106256827A (en) * | 2015-06-17 | 2016-12-28 | 上海和辉光电有限公司 | A kind of compound and synthetic method thereof and application |
| JP2021523231A (en) * | 2018-05-09 | 2021-09-02 | アプリノイア セラピューティクス インコーポレーテッド | Heteroaryl compounds and their use |
-
1990
- 1990-01-23 JP JP2011804A patent/JP2854908B2/en not_active Expired - Fee Related
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0669379A1 (en) * | 1994-02-25 | 1995-08-30 | MITSUI TOATSU CHEMICALS, Inc. | Quinophtalone compounds and polarizing films using same |
| WO2003086377A1 (en) * | 2002-04-18 | 2003-10-23 | Institute Of Medicinal Molecular Design. Inc. | Amide derivatives |
| GB2403474A (en) * | 2002-04-18 | 2005-01-05 | Inst Med Molecular Design Inc | Amide derivatives |
| JPWO2003086377A1 (en) * | 2002-04-18 | 2005-08-18 | 株式会社医薬分子設計研究所 | Amide derivatives |
| GB2403474B (en) * | 2002-04-18 | 2006-10-11 | Inst Med Molecular Design Inc | Amide derivatives |
| US7598418B2 (en) | 2002-04-18 | 2009-10-06 | Institute Of Medicinal Molecular Design, Inc. | Amide derivatives |
| JP4595059B2 (en) * | 2002-04-18 | 2010-12-08 | 株式会社医薬分子設計研究所 | Amide derivatives |
| CN106256827A (en) * | 2015-06-17 | 2016-12-28 | 上海和辉光电有限公司 | A kind of compound and synthetic method thereof and application |
| JP2021523231A (en) * | 2018-05-09 | 2021-09-02 | アプリノイア セラピューティクス インコーポレーテッド | Heteroaryl compounds and their use |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2854908B2 (en) | 1999-02-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Kawai et al. | A convenient preparation of bipyridines through ligand coupling reaction with a-sulfurane formed by treatment of methyl 2-pyridyl sulfoxide with grignard reagents | |
| EP1897875A1 (en) | Process for producing 1-pyridin-4-YL-indoles | |
| KR101578762B1 (en) | Copper phthalocyanine compound and near infrared absorption filter using the same | |
| CN114195711B (en) | Preparation method of quinoline-4 (1H) -ketone compound | |
| CA2187593A1 (en) | Naphthalenelactamimide fluorescence dyes | |
| US4973707A (en) | Acetylene bis-phthalic compounds and polyimides made therefrom | |
| JPH0414144B2 (en) | ||
| JPH03217459A (en) | Production of imide compound | |
| CN108947945B (en) | 1, 3-dihydroisobenzofuran derivative and synthetic method and application thereof | |
| Zimmermann et al. | Convenient syntheses of tetraarylmethane starting materials | |
| JP5130521B2 (en) | Heteropolycyclic phenazine compounds | |
| JPS61215663A (en) | Naphthalocyanine compound | |
| TW201927740A (en) | Compound and method for preparing chiral compound | |
| Helmholz et al. | Synthesis of Unsymmetrical Pyrrolo [3, 2-b] pyrrole-2, 5-diones and Bis (quinazolin-4-on-2-yls) by Double-Anion-Capture Reactions of Unsymmetrical Oxaldi (arylimidoyl) Dichlorides | |
| KR20010079690A (en) | Process for the preparation of substituted amido phthalocyanine derivatives and substituted amido phthalocyanine derivatives | |
| Yang et al. | A facile CN bond formation: One-pot reaction of phenols and amines via Smiles rearrangement | |
| KR20040023746A (en) | Fluorescent diketopyrrolopyrrole analogues | |
| CN112239456A (en) | A kind of preparation method of substituted 2,3-dihydroquinolone compound | |
| JPH0348666A (en) | Production of aromatic diamine compound | |
| GB2092130A (en) | 4-Oximino-1,2,3,4- tetrahydroquinoline Derivatives | |
| US5055580A (en) | Substituted polycylic derivatives of the 9-oxo-1,9a,10-triaza-9-hydroanthracene and method for coloring of native or synthetic materials | |
| JPH029882A (en) | Method for producing phthalocyanines | |
| CN110698490B (en) | Synthetic method of spiro-epoxy indole-cyclopentenobutenoic acid lactone compound | |
| JPH01157944A (en) | Methine compound, its production and optical information recording medium made thereof | |
| Wagger et al. | Synthesis of Racemic, N-Benzylated Neoechinulin A and Isoneoechinulin A |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |