JP6877563B2 - Compound manufacturing method and compound - Google Patents

Description

The present invention relates to a compound and a method for producing the same. More specifically, the present invention relates to a sulfonate of a hydrazine compound and a method for producing the same, and a method for producing an acid hydrazide compound derived from the hydrazine compound.

Several methods are known for producing sulfonates of hydrazine compounds. For example, in Example 3 of Patent Document 1, a compound represented by the formula (E-6) is synthesized by reacting hydrazine with 2-ethylhexanal, and then the compound represented by the formula (E-6) is synthesized. And ethanol and palladium-carbon catalyst are added to the autoclave, filled with hydrogen until the pressure reaches 40 atm, and stirred at 80 ° C. for 5 hours to prepare an ethanol solution of the compound represented by the formula (D-6). Then, it is described that naphthalene 1,5-disulfonic acid tetrahydrate is added to this ethanol solution to produce naphthalene 1,5-disulfonate, which is a compound represented by the formula (D-6). ..

JP-A-2010-018595

In the conventionally known method for producing a sulfonate compound of a hydrazine compound, a neutral hydrazine compound is produced and then the neutral hydrazine compound is reacted with a sulfonic acid to produce the sulfonate. Also in Patent Document 1, a compound represented by the formula (D-6), which is a neutral hydrazine compound, is synthesized, and this compound is reacted with naphthalene 1,5-disulfonic acid tetrahydrate to obtain a hydrazine compound. It is a sulfonate.

However, since the neutral hydrazine compound is a compound that is easily decomposed, it is necessary to sufficiently ventilate the compound, and it is necessary to pay attention to the safety at the time of production. Further, since the neutral hydrazine compound is a compound that is easily decomposed, the yield of the final product tends to decrease.

Therefore, an object of the present invention is to provide a method for producing a compound capable of producing a sulfonate of a hydrazine compound in a safe and high yield. Another object of the present invention is to provide a method for producing a compound capable of producing an acid hydrazide compound derived from a hydrazine compound in a safe and high yield. Another object of the present invention is to provide a sulfonate of a hydrazine compound having excellent safety.

式中、Ｒ^２１、Ｒ^２２およびＲ^３１は各々独立に脂肪族基、芳香族基または複素環基を表し、
ｍは正の整数を表し、ｑは正数を表し、
Ｒ^２１とＲ^２２は互いに結合して環を形成していてもよい。
＜２＞ 式（ＩＩ）で表される化合物のモル数に対する、式（ＩＩＩ）で表される化合物のモル数とｍの数との積の比が１．０以上である、＜１＞に記載の化合物の製造方法。
＜３＞ 式（ＩＶ）で表わされる化合物が式（Ｉ）で表わされる化合物である、＜１＞または＜２＞に記載の化合物の製造方法；

式中、Ｒ^２１、Ｒ^２２およびＲ^３２は各々独立に脂肪族基、芳香族基または複素環基を表し、ｐは正数を表し、Ｒ^２１とＲ^２２は互いに結合して環を形成していてもよい。
＜４＞ ＜１＞〜＜３＞のいずれかに記載の化合物の製造方法により式（ＩＶ）で表わされる化合物を得たのち、式（ＩＶ）で表わされる化合物と式（Ｖ）で表わされる化合物とを反応させることを含む、式（ＶＩ）で表わされる化合物の製造方法；

式中、Ｒ^２１、Ｒ^２２、Ｒ^３１、Ｒ^５１およびＲ^５２は各々独立に脂肪族基、芳香族基または複素環基を表し、ｍは正の整数を表し、ｑは正数を表し、Ｒ^２１とＲ^２２は互いに結合して環を形成していてもよい。
＜５＞ ＜１＞〜＜３＞のいずれかに記載の化合物の製造方法により式（ＩＶ）で表わされる化合物を得たのち、式（ＩＶ）で表わされる化合物と式（ＶＩＩ）で表わされる化合物とを反応させることを含む、式（ＶＩＩＩ）で表わされる化合物の製造方法；

式中、Ｒ^２１、Ｒ^２２、Ｒ^３１およびＲ^７１は各々独立に脂肪族基、芳香族基または複素環基を表し、Ｌ^７１は２価の連結基を表し、ｍは正の整数を表し、ｑは正数を表し、Ｒ^２１とＲ^２２は互いに結合して環を形成していてもよい。
＜６＞ 式（Ｉ）で表わされる化合物；

式中、Ｒ^２１、Ｒ^２２およびＲ^３２は各々独立に脂肪族基、芳香族基または複素環基を表し、ｐは正数を表し、Ｒ^２１とＲ^２２は互いに結合して環を形成していてもよい。
＜７＞ Ｒ^２１およびＲ^２２が各々独立に炭素数１〜１０の直鎖アルキル基である、＜６＞に記載の化合物。
＜８＞ Ｒ^３２がアリール基である、＜６＞または＜７＞に記載の化合物。
＜９＞ 示差走査熱量分析における発熱開始温度が１５０℃以上である、＜６＞〜＜８＞のいずれかに記載の化合物。
＜１０＞ ＜４＞または＜５＞に記載の化合物の製造方法に用いられる、＜６＞〜＜９＞のいずれかに記載の化合物。
＜１１＞ 式（ＶＩ）で表される化合物または式（ＶＩＩＩ）で表される化合物の前駆体である、＜６＞〜＜９＞のいずれかに記載の化合物；

式中、Ｒ^２１、Ｒ^２２およびＲ^５１は各々独立に脂肪族基、芳香族基または複素環基を表し、Ｌ^７１は２価の連結基を表し、Ｒ^２１とＲ^２２は互いに結合して環を形成していてもよい。According to the study of the present inventor, by reacting the compound represented by the formula (II) described later with the compound represented by the formula (III), hydrazine does not go through the process of producing a neutral hydrazine compound. They have found that a compound represented by the formula (II) described later, which is a sulfonate of a compound, can be produced, and have completed the present invention. Therefore, the present invention provides the following.
<1> A method for producing a compound represented by the formula (IV), which comprises reacting a compound represented by the formula (II) with a compound represented by the formula (III);

In the formula, R ²¹ , R ²² and R ³¹ each independently represent an aliphatic group, an aromatic group or a heterocyclic group.
m represents a positive integer, q represents a positive number,
R ²¹ and R ²² may be combined with each other to form a ring.
<2> In <1>, the ratio of the product of the number of moles of the compound represented by the formula (III) to the number of m to the number of moles of the compound represented by the formula (II) is 1.0 or more. The method for producing the compound described.
<3> The method for producing a compound according to <1> or <2>, wherein the compound represented by the formula (IV) is a compound represented by the formula (I);

In the formula, R ²¹ , R ²² and R ³² each independently represent an aliphatic group, an aromatic group or a heterocyclic group, p represents a positive number, and R ²¹ and R ²² combine with each other to form a ring. May be.
<4> After obtaining the compound represented by the formula (IV) by the method for producing the compound according to any one of <1> to <3>, the compound represented by the formula (IV) and the compound represented by the formula (V) are represented. A method for producing a compound represented by the formula (VI), which comprises reacting with the compound;

In the formula, R ²¹ , R ²² , R ³¹ , R ⁵¹ and R ⁵² independently represent an aliphatic group, an aromatic group or a heterocyclic group, m represents a positive integer and q represents a positive number. R ²¹ and R ²² may be coupled to each other to form a ring.
<5> After obtaining the compound represented by the formula (IV) by the method for producing the compound according to any one of <1> to <3>, the compound represented by the formula (IV) and the compound represented by the formula (VII) are represented. A method for producing a compound represented by the formula (VIII), which comprises reacting with the compound;

In the formula, R ²¹ , R ²² , R ³¹ and R ⁷¹ each independently represent an aliphatic group, an aromatic group or a heterocyclic group, L ⁷¹ represents a divalent linking group, and m represents a positive integer. , Q represent a positive number, and R ²¹ and R ²² may be coupled to each other to form a ring.
<6> Compound represented by formula (I);

In the formula, R ²¹ , R ²² and R ³² each independently represent an aliphatic group, an aromatic group or a heterocyclic group, p represents a positive number, and R ²¹ and R ²² combine with each other to form a ring. May be.
<7> ^{The compound according to <6>, wherein R 21} and R ²² are independently linear alkyl groups having 1 to 10 carbon atoms.
<8> The compound according to <6> or <7>, wherein ^{R 32 is an aryl group.}
<9> The compound according to any one of <6> to <8>, wherein the heat generation start temperature in the differential scanning calorimetry is 150 ° C. or higher.
<10> The compound according to any one of <6> to <9>, which is used in the method for producing the compound according to <4> or <5>.
<11> The compound according to any one of <6> to <9>, which is a precursor of the compound represented by the formula (VI) or the compound represented by the formula (VIII);

In the formula, R ²¹ , R ²² and R ⁵¹ each independently represent an aliphatic group, an aromatic group or a heterocyclic group, L ⁷¹ represents a divalent linking group, and R ²¹ and R ²² are bonded to each other. It may form a ring.

According to the present invention, it is possible to provide a method for producing a compound capable of producing a sulfonate of a hydrazine compound in a safe and high yield. Further, it is possible to provide a method for producing a compound capable of producing an acid hydrazide compound derived from a hydrazine compound in a safe and high yield. Further, it is possible to provide a sulfonate of a hydrazine compound having excellent safety.

Hereinafter, the contents of the present invention will be described in detail.
In the notation of a group (atomic group) in the present specification, the notation not describing substitution and non-substitution includes a group having a substituent as well as a group having no substituent. For example, the "alkyl group" includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
The numerical range represented by using "~" in the present specification means a range including the numerical values before and after "~" as the lower limit value and the upper limit value.
In the present specification, the total solid content means the total amount of the components excluding the solvent from all the components of the composition.
As used herein, the term "process" not only means an independent process, but also the term "process" as long as the intended action of the process is achieved even if it cannot be clearly distinguished from other processes. include.

式中、Ｒ^２１、Ｒ^２２およびＲ^３１は各々独立に脂肪族基、芳香族基または複素環基を表し、
ｍは正の整数を表し、ｑは正数を表し、
Ｒ^２１とＲ^２２は互いに結合して環を形成していてもよい。<Method for producing the compound represented by the formula (IV)>
The method for producing a compound of the present invention is a method for producing a compound represented by the formula (IV), which comprises reacting a compound represented by the formula (II) with a compound represented by the formula (III).

In the formula, R ²¹ , R ²² and R ³¹ each independently represent an aliphatic group, an aromatic group or a heterocyclic group.
m represents a positive integer, q represents a positive number,
R ²¹ and R ²² may be combined with each other to form a ring.

According to the present invention, the compound represented by the formula (IV), which is a sulfonate of the hydrazine compound, can be produced without going through the process of producing the neutral hydrazine compound. Therefore, the sulfonate of the hydrazine compound can be produced safely and in high yield.

The reaction between the compound represented by the formula (II) and the compound represented by the formula (III) may be carried out in the presence of a solvent or may be carried out without using a solvent. Further, the above-mentioned reaction may be carried out by adding an acid, a base, a salt, an inorganic compound or the like.

Examples of the solvent include water, amide-based solvents (for example, N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone), sulfone-based solvents (for example, sulfolane), sulfoxide-based solvents (for example, dimethylsulfoxide), and the like. Ureid solvents (eg tetramethylurea), alcohol solvents (eg methanol, octanol, benzyl alcohol), ether solvents (eg dioxane, anisole, tetrahydrofuran), ketone solvents (eg acetone, cyclohexanone), hydrocarbon solvents (eg acetone, cyclohexanone) For example, toluene, xylene, mesitylene, n-octane, n-dodecane), halogen solvents (eg chlorobenzene, tetrachloroethane, dichlorobenzene), pyridine solvents (eg pyridine, γ-picolin, 2,6-rutidine) and nitriles. Examples of the system solvent (for example, acetonitrile) are mentioned, and it is preferable to use these alone or in combination. Of these solvents, water, alcohol-based solvents, amide-based solvents, sulfone-based solvents, sulfoxide-based solvents, ureido-based solvents, ether-based solvents, hydrocarbon-based solvents, halogen-based solvents and nitrile-based solvents are preferable. Water, alcohol-based solvent, sulfone-based solvent, ether-based solvent, hydrocarbon-based solvent and halogen-based solvent are preferable, water, alcohol-based solvent and ether-based solvent are more preferable, and water and alcohol are particularly preferable. It is a system solvent.

The reaction temperature of the compound represented by the formula (II) and the compound represented by the formula (III) is preferably 0 to 250 ° C. The lower limit is preferably 10 ° C. or higher, more preferably 20 ° C. or higher, further preferably 25 ° C. or higher, and particularly preferably 30 ° C. or higher. The upper limit is preferably 200 ° C. or lower, more preferably 100 ° C. or lower, further preferably 70 ° C. or lower, and particularly preferably 60 ° C. or lower.

The compound represented by the formula (II) and the compound represented by the formula (III) are the number of moles and m of the compound represented by the formula (III) with respect to the number of moles of the compound represented by the formula (II). The reaction is carried out at a ratio of the product of and (the product of the number of moles of the compound represented by the formula (III) and the number of m / the number of moles of the compound represented by the formula (II)) of 0.01 or more. The reaction is preferably 0.1 or more, more preferably 0.8 or more, and 1.0 or more from the viewpoint of yield. Is even more preferable, and the reaction is particularly preferably at a ratio of 1.5 or more, and most preferably at a ratio of 1.8 or more. The upper limit of the above-mentioned ratio is preferably 10.0 or less, more preferably 6.0 or less, further preferably 5.0 or less, and 4.0 or less from the viewpoint of yield. More preferably, it is particularly preferably 3.0 or less, and most preferably 2.5 or less.

Next, the compound represented by the formula (II), the compound represented by the formula (III), and the compound represented by the formula (IV) will be described.

式（ＩＩ）中、Ｒ^２１およびＲ^２２は各々独立に脂肪族基、芳香族基または複素環基を表す。Ｒ^２１とＲ^２２は互いに結合して環を形成していてもよい。(Compound represented by formula (II))

In formula (II), R ²¹ and R ²² independently represent an aliphatic group, an aromatic group or a heterocyclic group, respectively. R ²¹ and R ²² may be combined with each other to form a ring.

The ^{number of carbon atoms of the aliphatic group represented by R 21} and R ²² is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 7. Examples of the type of the aliphatic group include an alkyl group, an alkenyl group, an alkynyl group and an aralkyl group, and an alkyl group or an alkenyl group is preferable, and an alkyl group is more preferable. The alkyl group, alkenyl group, alkynyl group and aralkyl group may have a substituent. Examples of the substituent include the group described in Substituent T described later.
The number of carbon atoms of the alkyl group is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, and most preferably 1 to 7. The alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear. Further, the alkyl group moiety of the cyclic alkyl group and the cyclic alkoxy group may be a monocyclic cycloalkyl group or a polycyclic alkyl group (bicycloalkyl group, tricycloalkyl group, etc.). ..
The alkenyl group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, further preferably 2 to 15 carbon atoms, particularly preferably 2 to 10 carbon atoms, and most preferably 2 to 7 carbon atoms. The alkenyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
The alkynyl group preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, further preferably 2 to 15 carbon atoms, particularly preferably 2 to 10 carbon atoms, and most preferably 2 to 7 carbon atoms. The alkynyl group may be linear, branched or cyclic, preferably linear or branched, and more preferably linear.
The carbon number of the aralkyl group is preferably 7 to 30, more preferably 7 to 20, and even more preferably 7 to 15. The alkyl moiety of the aralkyl group is the same as the above alkyl group. The aryl moiety of the aralkyl group is the same as the following aryl group.

Examples of the aromatic group include an aryl group. The number of carbon atoms of the aromatic group is preferably 6 to 40, more preferably 6 to 30, further preferably 6 to 20, particularly preferably 6 to 15, and most preferably 6 to 12. As the aryl group, a phenyl group and a naphthyl group are preferable, and a phenyl group is more preferable. The aryl group may have a substituent. Examples of the substituent include the group described in Substituent T described later.

The heterocycle in the heterocyclic group preferably contains a 5- or 6-membered saturated or unsaturated heterocycle. It is preferable that the site of the carbon atom of the heterocyclic group is a linking hand. The heterocycle may be fused with an aliphatic ring, an aromatic ring or another heterocycle. Examples of the heteroatom constituting the ring of the heterocycle include B, N, O, S, Se and Te, and N, O and S are preferable.
The number of carbon atoms of the preferred heterocyclic group is 1 to 40, more preferably 1 to 30, and even more preferably 1 to 20. Examples of saturated heterocycles in the heterocyclic group include pyrrolidine ring, morpholine ring, 2-bora-1,3-dioxolane ring and 1,3-thiazolidine ring. Examples of the unsaturated heterocycle in the heterocyclic group include an imidazole ring, a thiazole ring, a benzothiazole ring, a benzoxazole ring, a benzotriazole ring, a benzoselenazole ring, a pyridine ring, a pyrimidine ring and a quinoline ring. The heterocyclic group may have a substituent. Examples of the substituent include the group described in Substituent T described later.

In the formula (II), R ²¹ and R ²² are preferably an aliphatic group or an aromatic group, respectively, and are an aliphatic group having 1 to 30 carbon atoms or an aromatic group having 6 to 30 carbon atoms. Is more preferable, an aliphatic group having 1 to 20 carbon atoms is further preferable, and an alkyl group having 1 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms is even more preferable. It is even more preferable that it is an alkyl group of 1 to 10, particularly preferably a linear alkyl group having 1 to 10 carbon atoms, and most preferably a linear alkyl group having 1 to 7 carbon atoms.

In formula (II), R ²¹ and R ²² may be bonded to each other to form a ring. The ^{ring formed by combining R 21} and R ²² is preferably a 5- or 6-membered ring.

(Substituent T)
As the substituent T,
Halogen atom (eg chlorine atom, bromine atom, iodine atom);
Alkyl group [straight, branched, cyclic alkyl group. Specifically, a linear or branched alkyl group (preferably a linear or branched alkyl group having 1 to 30 carbon atoms, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a t-butyl group, n -Octyl group, eicosyl group, 2-chloroethyl group, 2-cyanoethyl group, 2-ethylhexyl group), cycloalkyl group (preferably cycloalkyl group having 3 to 30 carbon atoms, for example, cyclohexyl group, cyclopentyl group, 4- n-dodecylcyclohexyl group), bicycloalkyl group (preferably a bicycloalkyl group having 5 to 30 carbon atoms, that is, a monovalent group obtained by removing one hydrogen atom from a bicycloalkane having 5 to 30 carbon atoms, for example, bicyclo [ It also includes 1,2,2] heptan-2-yl group, bicyclo [2,2,2] octane-3-yl group), and tricyclo structure having many ring structures. The alkyl group among the substituents described below (for example, the alkyl group of the alkylthio group) also represents the alkyl group of such a concept. ];
Alkenyl group [straight, branched, cyclic alkenyl group. Specifically, a linear or branched alkenyl group (preferably a linear or branched alkenyl group having 2 to 30 carbon atoms, for example, a vinyl group, an allyl group, a prenyl group, a geranyl group, an oleyl group), a cycloalkenyl group. (Preferably, it is a cycloalkenyl group having 3 to 30 carbon atoms, that is, a monovalent group from which one hydrogen atom of cycloalkene having 3 to 30 carbon atoms has been removed. For example, 2-cyclopenten-1-yl group, 2 -Cyclohexene-1-yl group), bicycloalkenyl group (preferably a substituted or unsubstituted bicycloalkenyl group having 5 to 30 carbon atoms, that is, a monovalent by removing one hydrogen atom of bicycloalkene having one double bond. It is a group, for example, a bicyclo [2,2,1] hept-2-ene-1-yl group, a bicyclo [2,2,2] octo-2-en-4-yl group). .. ];
An alkynyl group (preferably a linear or branched alkynyl group having 2 to 30 carbon atoms; for example, an ethynyl group, a propargyl group, a trimethylsilylethynyl group;

Aryl groups (preferably aryl groups having 6 to 30 carbon atoms, such as phenyl group, p-tolyl group, naphthyl group, m-chlorophenyl group, o-hexadecanoylaminophenyl group);
Heterocyclic group (preferably a monovalent group obtained by removing one hydrogen atom from an aromatic or non-aromatic heterocyclic compound having 5 or 6 members, and more preferably 5 or 6 members having 3 to 30 carbon atoms. Aromatic heterocyclic groups such as 2-furyl group, 2-thienyl group, 2-pyrimidinyl group, 2-benzothiazolyl group);
Cyano group;
Hydroxy group;
Nitro group;
Carboxylic group;
Alkoxy groups (preferably linear or branched alkoxy groups having 1 to 30 carbon atoms, such as methoxy group, ethoxy group, isopropoxy group, t-butoxy group, n-octyloxy group, 2-methoxyethoxy group);
Aryloxy group (preferably an aryloxy group having 6 to 30 carbon atoms, for example, a phenoxy group, a 2-methylphenoxy group, a 4-t-butylphenoxy group, a 3-nitrophenoxy group, a 2-tetradecanoylaminophenoxy group. );
A silyloxy group (preferably a silyloxy group having 3 to 20 carbon atoms, for example, a trimethylsilyloxy group, a t-butyldimethylsilyloxy group);
Heterocyclic oxy group (preferably a heterocyclic oxy group having 2 to 30 carbon atoms, for example, 1-phenyltetrazole-5-oxy group, 2-tetrahydropyranyloxy group);
Acyloxy group (preferably formyloxy group, alkylcarbonyloxy group having 2 to 30 carbon atoms, arylcarbonyloxy group having 6 to 30 carbon atoms, for example, formyloxy group, acetyloxy group, pivaloyloxy group, stearoyloxy group, benzoyloxy group. Group, p-methoxyphenylcarbonyloxy group);

Carbamoyloxy group (preferably a carbamoyloxy group having 1 to 30 carbon atoms, for example, N, N-dimethylcarbamoyloxy group, N, N-diethylcarbamoyloxy group, morpholinocarbonyloxy group, N, N-di-n- Octylaminocarbonyloxy group, Nn-octylcarbamoyloxy group);
Alkoxycarbonyloxy groups (preferably alkoxycarbonyloxy groups having 2 to 30 carbon atoms, such as methoxycarbonyloxy groups, ethoxycarbonyloxy groups, t-butoxycarbonyloxy groups, n-octylcarbonyloxy groups);
Aryloxycarbonyloxy group (preferably an aryloxycarbonyloxy group having 7 to 30 carbon atoms; for example, a phenoxycarbonyloxy group, a p-methoxyphenoxycarbonyloxy group, a pn-hexadecyloxyphenoxycarbonyloxy group);
Amino group (preferably an amino group, an alkylamino group having 1 to 30 carbon atoms, an anilino group having 6 to 30 carbon atoms, for example, an amino group, a methylamino group, a dimethylamino group, an anilino group, an N-methyl-anilino group. , Diphenylamino group);
Acylamino group (preferably formylamino group, alkylcarbonylamino group having 1 to 30 carbon atoms, arylcarbonylamino group having 6 to 30 carbon atoms, for example, formylamino group, acetylamino group, pivaloylamino group, lauroylamino group, benzoyl. Amino group, 3,4,5-tri-n-octyloxyphenylcarbonylamino group);

Aminocarbonylamino group (preferably an aminocarbonylamino group having 1 to 30 carbon atoms; for example, a carbamoylamino group, an N, N-dimethylaminocarbonylamino group, an N, N-diethylaminocarbonylamino group, a morpholinocarbonylamino group);
Alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having 2 to 30 carbon atoms, for example, a methoxycarbonylamino group, an ethoxycarbonylamino group, a t-butoxycarbonylamino group, an n-octadecyloxycarbonylamino group, an N-methyl-methoxy group. Carbonyl group);
Aryloxycarbonylamino group (preferably an aryloxycarbonylamino group having 7 to 30 carbon atoms; for example, a phenoxycarbonylamino group, a p-chlorophenoxycarbonylamino group, an mn-octyloxyphenoxycarbonylamino group);
Sulfamoylamino group (preferably a sulfamoylamino group having 0 to 30 carbon atoms; for example, a sulfamoylamino group, an N, N-dimethylaminosulfonylamino group, an Nn-octylaminosulfonylamino group);
Alkyl or arylsulfonylamino groups (preferably alkylsulfonylamino groups having 1 to 30 carbon atoms, arylsulfonylamino groups having 6 to 30 carbon atoms, such as methylsulfonylamino groups, butylsulfonylamino groups, phenylsulfonylamino groups, 2, 3,5-Trichlorophenylsulfonylamino group, p-methylphenylsulfonylamino group);
Mercapto group;
Alkylthio group (preferably an alkylthio group having 1 to 30 carbon atoms, for example, a methylthio group, an ethylthio group, an n-hexadecylthio group);
Arylthio group (preferably an arylthio group having 6 to 30 carbon atoms, for example, a phenylthio group, a p-chlorophenylthio group, an m-methoxyphenylthio group);
Heterocyclic thio group (preferably a heterocyclic thiogroup having 2 to 30 carbon atoms, for example, 2-benzothiazolylthio group, 1-phenyltetrazole-5-ylthio group);

Sulfamoyl group (preferably a sulfamoyl group having 0 to 30 carbon atoms, for example, N-ethylsulfamoyl group, N- (3-dodecyloxypropyl) sulfamoyl group, N, N-dimethylsulfamoyl group, N-acetylsul. Famoyl group, N-benzoyl sulfamoyl group, N- (N'-phenylcarbamoyl) sulfamoyl group);
Sulfone group;
Alkyl or arylsulfinyl groups (preferably alkylsulfinyl groups having 1 to 30 carbon atoms, arylsulfinyl groups having 6 to 30 carbon atoms, for example, methylsulfinyl groups, ethylsulfinyl groups, phenylsulfinyl groups, p-methylphenylsulfinyl groups);
Alkyl or arylsulfonyl groups (preferably alkylsulfonyl groups with 1 to 30 carbon atoms, arylsulfonyl groups with 6 to 30 carbon atoms, such as methylsulfonyl groups, ethylsulfonyl groups, phenylsulfonyl groups, p-methylphenylsulfonyl groups);

An acyl group (preferably a formyl group, an alkylcarbonyl group having 2 to 30 carbon atoms, an arylcarbonyl group having 7 to 30 carbon atoms, a heterocyclic carbonyl group bonded to the carbonyl group with a carbon atom having 4 to 30 carbon atoms, for example. , Acetyl group, pivaloyl group, 2-chloroacetyl group, stearoyl group, benzoyl group, pn-octyloxyphenylcarbonyl group, 2-pyridylcarbonyl group, 2-furylcarbonyl group);
Aryloxycarbonyl groups (preferably aryloxycarbonyl groups having 7 to 30 carbon atoms, such as phenoxycarbonyl groups, o-chlorophenoxycarbonyl groups, m-nitrophenoxycarbonyl groups, pt-butylphenoxycarbonyl groups);
Alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 30 carbon atoms; for example, a methoxycarbonyl group, an ethoxycarbonyl group, a t-butoxycarbonyl group, an n-octadecyloxycarbonyl group);
Carbamoyl group (preferably a carbamoyl group having 1 to 30 carbon atoms, for example, a carbamoyl group, an N-methylcarbamoyl group, an N, N-dimethylcarbamoyl group, an N, N-di-n-octylcarbamoyl group, N- (methyl). Sulfonyl) carbamoyl group);
Aryl or heterocyclic azo groups (preferably arylazo groups having 6 to 30 carbon atoms, heterocyclic azo groups having 3 to 30 carbon atoms, for example, phenylazo groups, p-chlorophenylazo groups, 5-ethylthio-1,3,4- Thianazol-2-ylazo group);
Imid group (preferably N-succinimide group, N-phthalimide group);
Phosphino group (preferably a phosphino group having 2 to 30 carbon atoms, for example, a dimethylphosphino group, a diphenylphosphino group, a methylphenoxyphosphino group).
A phosphinyl group (preferably a phosphinyl group having 2 to 30 carbon atoms, for example, a phosphinyl group, a dioctyloxyphosphinyl group, a diethoxyphosphinyl group);
A phosphinyloxy group (preferably a phosphinyloxy group having 2 to 30 carbon atoms; for example, a diphenoxyphosphinyloxy group, a dioctyloxyphosphinyloxy group);
A phosphinylamino group (preferably a phosphinylamino group having 2 to 30 carbon atoms, for example, a dimethoxyphosphinylamino group, a dimethylaminophosphinylamino group);
A silyl group (preferably a silyl group having 3 to 30 carbon atoms, for example, a trimethylsilyl group, a t-butyldimethylsilyl group, a phenyldimethylsilyl group) can be mentioned.

Among the groups listed above, for a group having a hydrogen atom, one or more hydrogen atoms may be substituted with the above-mentioned substituent T. Examples of such functional groups include alkylcarbonylaminosulfonyl groups, arylcarbonylaminosulfonyl groups, alkylsulfonylaminocarbonyl groups and arylsulfonylaminocarbonyl groups. Specific examples include a methylsulfonylaminocarbonyl group, a p-methylphenylsulfonylaminocarbonyl group, an acetylaminosulfonyl group, a benzoylaminosulfonyl group and the like.

Specific examples of the compound represented by the formula (II) include the following compounds.

式中、Ｒ^３１は脂肪族基、芳香族基または複素環基を表し、ｍは正の整数を表す。(Compound represented by formula (III))

In the formula, R ³¹ represents an aliphatic group, an aromatic group or a heterocyclic group, and m represents a positive integer.

Examples of the aliphatic group, aromatic group or heterocyclic group represented by R ³¹ include those described in ^{R 21} and R ^{22 described above.} Among them, R ³¹ is preferably an aliphatic group or an aromatic group, more preferably an aromatic group, and the yield of the compound represented by the formula (IV) and the yield of the compound represented by the formula (IV) and the compound represented by the formula (IV). From the viewpoint of stability, it is more preferably an aryl group. Specifically, R ³¹ is preferably an aliphatic group having 1 to 15 carbon atoms or an aromatic group having 6 to 15 carbon atoms, and an aliphatic group having 1 to 12 carbon atoms or an aliphatic group having 6 to 12 carbon atoms. It is more preferably an aromatic group, further preferably an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 12 carbon atoms, and a linear alkyl group having 1 to 4 carbon atoms, a phenyl group or a naphthalene. It is even more preferably a 1,5-diyl group, particularly preferably a methyl group, a phenyl group or a p-tolyl group, and most preferably a phenyl group or a p-tolyl group.

m represents a positive integer, preferably 1 to 3, more preferably 1 or 2, and even more preferably 1 from the viewpoint of the stability of the compound represented by the formula (IV).

Specific examples of the compound represented by the formula (III) include the following compounds.

式中、Ｒ^２１、Ｒ^２２およびＲ^３１は各々独立に脂肪族基、芳香族基または複素環基を表し、ｍは正の整数を表し、ｑは正数を表し、Ｒ^２１とＲ^２２は互いに結合して環を形成していてもよい。(Compound represented by formula (IV))

In the formula, R ²¹ , R ²² and R ³¹ independently represent an aliphatic group, an aromatic group or a heterocyclic group, m represents a positive integer, q represents a positive number, and R ²¹ and R ^{22 represent positive numbers.} They may be combined with each other to form a ring.

R ²¹ , R ²² , R ³¹ , ^{and m are synonymous with R 21} , R ²² in formula (II) and R ³¹ , m in formula (III), and the preferred ranges are also the same. In equation (IV), q represents a positive number. The product of m and q is preferably 1 to 3, more preferably 1.5 to 2.5, further preferably 1.8 to 2.3, and particularly preferably 2.

In formula (IV), m is preferably 1. That is, the compound represented by the formula (IV) is preferably a compound represented by the following formula (I). The compound represented by the formula (I) has a high thermal decomposition temperature and is excellent in stability. Further, by producing a compound represented by the formula (VI) or a compound represented by the formula (VIII) described later using the compound represented by the formula (I), these compounds can be produced in a high yield. Can be manufactured. Therefore, it can be preferably used as a precursor of these compounds. The compound represented by the formula (I) is also the compound of the present invention.

In the formula, R ²¹ , R ²² and R ³² each independently represent an aliphatic group, an aromatic group or a heterocyclic group, p represents a positive number, and R ²¹ and R ²² combine with each other to form a ring. May be. R ²¹ , R ²² , and R ³² are ^{synonymous with R 21} and R ^{22 of} the formula (II) and R ³¹ of the formula (III), and the preferable ranges are also the same. In the formula (I), p represents a positive number, preferably 1-3, more preferably 1.5 to 2.5, further preferably 1.8 to 2.3, and particularly preferably 2. Specific examples of the compound represented by the formula (I) include the following compounds.

Among the compounds represented by the formula (IV), specific examples of the compounds other than the compound represented by the formula (I) include the following compounds.

式中、Ｒ^２１、Ｒ^２２、Ｒ^３１、Ｒ^５１およびＲ^５２は各々独立に脂肪族基、芳香族基または複素環基を表し、ｍは正の整数を表し、ｑは正数を表し、Ｒ^２１とＲ^２２は互いに結合して環を形成していてもよい。<Method for producing a compound represented by the formula (VI)>
Next, a method for producing the compound represented by the formula (VI) will be described.
In the method for producing a compound represented by the formula (VI) in the present invention, a compound represented by the formula (IV) is obtained by the method described above, and then a compound represented by the formula (IV) and a compound represented by the formula (V) are obtained. Including reacting with.

In the formula, R ²¹ , R ²² , R ³¹ , R ⁵¹ and R ⁵² independently represent an aliphatic group, an aromatic group or a heterocyclic group, m represents a positive integer and q represents a positive number. R ²¹ and R ²² may be coupled to each other to form a ring.

In the method for producing a compound represented by the formula (VI), the compound represented by the formula (IV) is purified from a reaction product of the compound represented by the formula (II) and the compound represented by the formula (III). After taking out, the compound represented by the formula (VI) may be produced by reacting with the compound represented by the formula (V), without taking out the compound represented by the formula (IV) from the above-mentioned reactant. The compound represented by the formula (VI) can also be produced by reacting the reactant with the compound represented by the formula (V).

The reaction between the compound represented by the formula (IV) and the compound represented by the formula (V) may be carried out in the presence of a solvent or may be carried out without using a solvent. Further, the above-mentioned reaction may be carried out by adding an acid, a base, a salt, an inorganic compound or the like.

Examples of the solvent include amide-based solvents (for example, N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone), sulfone-based solvents (for example, sulfolane), sulfoxide-based solvents (for example, dimethylsulfoxide), and ureido-based solvents. Solvents (eg tetramethylurea), alcohol solvents (eg methanol, octanol, benzyl alcohol), ether solvents (eg dioxane, anisole, tetrahydrofuran), ketone solvents (eg acetone, cyclohexanone), hydrocarbon solvents (eg toluene) , Xylene, mesitylene, n-octane, n-dodecane), halogen-based solvents (eg chlorobenzene, tetrachloroethane, dichlorobenzene), pyridine-based solvents (eg pyridine, γ-picolin, 2,6-rutidine), nitrile-based solvents (For example, acetonitrile) and water can be used alone or in admixture. Further, the compound represented by the formula (IV) can also be used as a solvent. Of these solvents, a sulfone solvent, a sulfoxide solvent, an alcohol solvent, an ether solvent, a ketone solvent, a hydrocarbon solvent, a halogen solvent and water are preferable, and a sulfone solvent and an ether solvent are more preferable. , Ketone-based solvent, hydrocarbon-based solvent, halogen-based solvent and water, more preferably ether-based solvent, hydrocarbon-based solvent, halogen-based solvent, and most preferably hydrocarbon-based solvent.

The reaction temperature of the compound represented by the formula (IV) and the compound represented by the formula (V) is preferably 0 to 250 ° C. The lower limit is preferably 20 ° C. or higher, more preferably 50 ° C. or higher, and even more preferably 90 ° C. or higher. The upper limit is preferably 200 ° C. or lower, more preferably 180 ° C. or lower, and even more preferably 160 ° C. or lower.

In the compound represented by the formula (IV) and the compound represented by the formula (V), the ratio of the number of moles of the compound represented by the formula (V) to the number of moles of the compound represented by the formula (IV) is 0. It is preferable to react at a ratio of 1 or more, more preferably 1.0 or more, further preferably 1.5 or more, and 1.6 or more. It is more preferable to react with the above, particularly preferably with a ratio of 1.8 or more, and most preferably with a ratio of 2.0 or more. The upper limit of the above-mentioned ratio is preferably 20.0 or less, more preferably 15.0 or less, further preferably 10.0 or less, and even more preferably 4.0 or less. , 3.0 or less is particularly preferable, and 2.6 or less is most preferable.

Next, the compound represented by the formula (V) and the compound represented by the formula (VI) will be described.

(Compound represented by formula (V))

In the formula, R ⁵¹ and R ⁵² each independently represent an aliphatic group, an aromatic group or a heterocyclic group.
Examples of the aliphatic group, aromatic group or heterocyclic group represented by R ⁵¹ and R ⁵² include those described in ^{R 21} and R ^{22 described above.}

R ⁵¹ is preferably an aliphatic group or an aromatic group, more preferably an aliphatic group having 1 to 30 carbon atoms or an aromatic group having 6 to 20 carbon atoms, and an aliphatic group having 1 to 20 carbon atoms. It is more preferably a group or an aromatic group having 6 to 20 carbon atoms, further preferably an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, a phenyl group or an naphthyl group, and carbon. It is particularly preferably an alkyl group or a phenyl group having a number of 1 to 15, and particularly preferably an alkyl group or a phenyl group having 1 to 10 carbon atoms. These groups may further have a substituent. Examples of the substituent include the group described in the above-mentioned Substituent T.

R ⁵² is preferably an aliphatic group or an aromatic group, more preferably an aliphatic group having 1 to 20 carbon atoms or an aromatic group having 6 to 20 carbon atoms, and an aliphatic group having 1 to 10 carbon atoms. It is more preferably a group or an aromatic group having 6 to 10 carbon atoms. Further, R ⁵² is preferably an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, a phenyl group or a naphthyl group, and may be an alkyl group or a phenyl group having 1 to 15 carbon atoms. It is more preferably an alkyl group or a phenyl group having 1 to 10 carbon atoms, and most preferably an alkyl group or a phenyl group having 1 to 3 carbon atoms. These groups may further have a substituent. Examples of the substituent include the group described in the above-mentioned Substituent T.

Specific examples of the compound represented by the formula (V) include the following compounds.

(Compound represented by formula (VI))

In the formula, R ²¹ , R ²² and R ⁵¹ each independently represent an aliphatic group, an aromatic group or a heterocyclic group, and R ²¹ and R ²² may be bonded to each other to form a ring. ^{R 21} and ^{R 22} in formula (VI) has the same meaning as ^{R 21} and ^{R 22} in formula (II), ^{R 51} in formula (VI) has the same meaning as ^{R 51} in Formula (V), at a preferred range Is the same. Specific examples of the compound represented by the formula (VI) include the following compounds.

式中、Ｒ^２１、Ｒ^２２、Ｒ^３１およびＲ^７１は各々独立に脂肪族基、芳香族基または複素環基を表し、Ｌ^７１は２価の連結基を表し、ｍは正の整数を表し、ｑは正数を表し、Ｒ^２１とＲ^２２は互いに結合して環を形成していてもよい。<Method for producing the compound represented by the formula (VIII)>
Next, a method for producing the compound represented by the formula (VIII) will be described.
In the method for producing a compound represented by the formula (VIII) in the present invention, a compound represented by the formula (IV) is obtained by the method described above, and then a compound represented by the formula (IV) and a compound represented by the formula (VII) are obtained. Including reacting with.

In the formula, R ²¹ , R ²² , R ³¹ and R ⁷¹ each independently represent an aliphatic group, an aromatic group or a heterocyclic group, L ⁷¹ represents a divalent linking group, and m represents a positive integer. , Q represent a positive number, and R ²¹ and R ²² may be coupled to each other to form a ring.

In the method for producing a compound represented by the formula (VIII), the compound represented by the formula (IV) is purified from a reaction product of the compound represented by the formula (II) and the compound represented by the formula (III). After taking out, the compound represented by the formula (VIII) may be produced by reacting with the compound represented by the formula (VII), without taking out the compound represented by the formula (IV) from the above-mentioned reactant. The compound represented by the formula (VIII) can also be produced by reacting the reaction product with the compound represented by the formula (VII).

The reaction between the compound represented by the formula (IV) and the compound represented by the formula (VII) may be carried out in the presence of a solvent or may be carried out without using a solvent. Examples of the solvent include those described in the method for producing a compound represented by the formula (VI), and the preferred range is also the same. Further, the above-mentioned reaction may be carried out by adding an acid, a base, a salt, an inorganic compound or the like.

The reaction temperature of the compound represented by the formula (IV) and the compound represented by the formula (VII) is preferably 0 to 250 ° C. The lower limit is preferably 20 ° C. or higher, more preferably 50 ° C. or higher, and even more preferably 90 ° C. or higher. The upper limit is preferably 200 ° C. or lower, more preferably 180 ° C. or lower, and even more preferably 160 ° C. or lower.

In the compound represented by the formula (IV) and the compound represented by the formula (VII), the ratio of the number of moles of the compound represented by the formula (VII) to the number of moles of the compound represented by the formula (IV) is 0. The reaction is preferably at a rate of 0.05 or more, more preferably at a rate of 0.5 or more, further preferably at a rate of 0.75 or more, and at a rate of 0.8 or more. It is more preferable to react with, particularly preferably to react at a ratio of 0.9 or more, and most preferably to react at a ratio of 1.0 or more. The upper limit of the above-mentioned ratio is preferably 10.0 or less, more preferably 7.5 or less, further preferably 5.0 or less, and even more preferably 2.0 or less. , 1.5 or less is particularly preferable, and 1.3 or less is most preferable.

Next, the compound represented by the formula (VII) and the compound represented by the formula (VIII) will be described.

式中、Ｒ^７１は脂肪族基、芳香族基または複素環基を表し、Ｌ^７１は２価の連結基を表す。(Compound represented by formula (VII))

In the formula, R ⁷¹ represents an aliphatic group, an aromatic group or a heterocyclic group, and L ⁷¹ represents a divalent linking group.

Examples of the aliphatic group, aromatic group or heterocyclic group represented by R ⁷¹ include those described in ^{R 21} and R ^{22 described above.} R ⁷¹ is preferably an aliphatic group or an aromatic group, more preferably an aliphatic group having 1 to 20 carbon atoms or an aromatic group having 6 to 20 carbon atoms, and an aliphatic group having 1 to 10 carbon atoms. It is more preferably a group or an aromatic group having 6 to 10 carbon atoms. Further, R ⁷¹ is preferably an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, a phenyl group or a naphthyl group, and more preferably an alkyl group or a phenyl group having 1 to 15 carbon atoms. It is more preferably an alkyl group or a phenyl group having 1 to 10 carbon atoms, and most preferably an alkyl group or a phenyl group having 1 to 3 carbon atoms. These groups may further have a substituent. Examples of the substituent include the group described in the above-mentioned Substituent T.

The ^{divalent linking group represented by L 71} consists of an alkylene group, an arylene group, a heterocyclic group, -O-, -S-, -CO-, -COO-, -OCO-, or a combination of these groups. The group is preferably an alkylene group or an arylene group, more preferably an alkylene group having 1 to 10 carbon atoms or an arylene group having 6 to 10 carbon atoms, and a methylene group, an ethylene group or an o-phenylene group. Is particularly preferable, and a methylene group is most preferable.

Specific examples of the compound represented by the formula (VII) include the following compounds.

(Compound represented by formula (VIII))

In the formula, R ²¹ and R ²² independently represent an aliphatic group, an aromatic group or a heterocyclic group, L ⁷¹ represents a divalent linking group, and R ²¹ and R ²² are bonded to each other to form a ring. You may be doing it.
^{R 21} and ^{R 22} in formula (VIII) has the same meaning as ^{R 21} and ^{R 22} of formula (II), ^{L 71} in the formula (VIII) has the same meaning as ^{L 71} in the formula (VII), preferred are The range is similar. Specific examples of the compound represented by the formula (VIII) include the following compounds.

<Compound>
Next, the compound of the present invention will be described.
The compound of the present invention is a compound represented by the above-mentioned formula (I).
The compound of the present invention has a high thermal decomposition temperature and is excellent in stability. The compound of the present invention can be preferably used as a raw material for pigments, pharmaceuticals, pesticides and the like. In addition, the compound of the present invention can be preferably used as a raw material for producing the compound represented by the above formula (VI) or the compound represented by the formula (VIII). That is, the compound of the present invention can be preferably used as a precursor of the above-mentioned compound.

The compound of the present invention preferably has a heat generation start temperature of 150 ° C. or higher, more preferably 180 ° C. or higher, and even more preferably 200 ° C. or higher in the differential scanning calorimetry. The upper limit of the heat generation start temperature is not particularly limited. The higher the value, the better the stability, which is preferable. For example, the upper limit can be 380 ° C. or lower. The heat generation start temperature in the differential scanning calorimetry is the temperature at the intersection of the tangent line of the heat generation peak and the baseline that appears when the temperature rises from the room temperature (25 ° C.) at a temperature rise rate of 10 ° C./min. is there.

Hereinafter, the present invention will be described in more detail with reference to examples. The materials, amounts used, ratios, treatment contents, treatment procedures, etc. shown in the following examples can be appropriately changed as long as they do not deviate from the gist of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. Unless otherwise specified, "part" and "%" are based on mass.

<Manufacturing Example 1> (Example 1)
Compound (VIII-1) was synthesized according to the following scheme.

62.6 g of compound (1) (hydrazine monohydrate), 109 mL of isopropyl alcohol and 125.4 g of formic acid were placed in a three-necked flask, and the mixture was stirred under heating under reflux for 3 hours. Then, the flask was cooled with water, stirred at 15 ° C. for 1 hour, and the precipitated crystals were filtered and dried to obtain 84.7 g of compound (2) (yield 96%).
Next, 69.9 g of compound (2), 332.0 g of potassium carbonate, 105 mL of N, N-dimethylacetamide and 253 mL of acetonitrile were placed in a three-necked flask, and 260.6 g of n-bromobutane was added dropwise under heating under reflux. After the dropping, the mixture was heated under reflux for 3 hours as it was, cooled, and 776 mL of ethyl acetate and 777 mL of water were added and stirred to carry out extraction. The obtained ethyl acetate phase was washed 3 times with a saline solution prepared by mixing 11.6 g of salt and 817 mL of water, and then concentrated with a rotary evaporator to obtain 152.7 g of compound (II-1) (152.7 g of compound (II-1)). Yield 96%).
Next, 100.1 g of compound (II-1), 190.2 g of p-toluenesulfonic acid monohydrate, and 230 mL of methanol were placed in a three-necked flask and stirred at 40 ° C. for 2 hours. Then, after concentrating with a rotary evaporator, 500 mL of ethyl acetate was added to disperse the crystals, and then the crystals were filtered and dried to obtain 244.3 g of compound (I-1) (yield 100%). The total yield from hydrazine monohydrate to compound (I-1) was 92%.
Next, a Dean Stark condenser was attached to a three-necked flask, 48.9 g of compound (I-1), 489 mL of xylene, and 26.4 g of dimethyl malonate were added, and a distillation product containing water and the like accumulated in the Dean Stark condenser. The mixture was stirred under heating and reflux for 6 hours. On the way, the same amount of xylene as the extracted distillate was added. Then, the reaction mixture was cooled to 120 ° C., 240 mL of water was added dropwise, and the mixture was stirred under heating under reflux for 1 hour. This was cooled to room temperature, 240 mL of water was added, and the mixture was extracted. The obtained aqueous phase was neutralized with an aqueous sodium hydroxide solution, and then extracted with 240 mL of toluene. The obtained toluene phase and the xylene phase obtained in the previous extraction were combined and washed with 240 mL of 0.02 mol / L hydrochloric acid, and then in an aqueous solution prepared by dissolving 4.2 g of sodium hydrogen carbonate and 76 g of salt in 440 mL of water. After washing, 76 g of sodium chloride was washed with an aqueous solution dissolved in 440 mL of water. Then, the mixture was concentrated on a rotary evaporator, and the obtained residue was purified by silica gel column chromatography to obtain 20.5 g of compound (VIII-1) (yield 96%). The total yield from hydrazine monohydrate to compound (VIII-1) was 88%.

<Production Example 2> (Synthesis of compound (VIII-1) that does not extract compound (I-1))
Compound (II-1) was synthesized in the same manner as in Production Example 1.
Next, attach a Dean Stark condenser to a three-necked flask, add 20.0 g of compound (II-1), 38.0 g of p-toluenesulfonic acid monohydrate, and 50 mL of methanol, and add them at 40 ° C. for 2 hours. , Heated and stirred. 489 mL of xylene was added thereto to raise the external temperature, and the mixture was heated to an internal temperature of 135 ° C. while removing distillates. Further, 300 mL of xylene and 26.4 g of dimethyl malonate were added thereto, and the mixture was stirred under heating under reflux for 6 hours while removing the distillate containing water and the like accumulated in the Dean Stark condenser. On the way, the same amount of xylene as the extracted distillate was added. Then, the reaction mixture was cooled to 120 ° C., 240 mL of water was added dropwise, and the mixture was stirred under heating under reflux for 1 hour. This was cooled to room temperature, 240 mL of water was added, and the mixture was extracted. The obtained aqueous phase was neutralized with an aqueous sodium hydroxide solution, and then extracted with 240 mL of toluene. The obtained toluene phase and the xylene phase obtained in the previous extraction were combined and washed with 240 mL of 0.02 mol / L hydrochloric acid, and then washed with an aqueous solution of 4.2 g of sodium hydrogen carbonate and 76 g of salt in 440 mL of water. Then, 76 g of sodium chloride was washed with an aqueous solution dissolved in 440 mL of water. Then, the mixture was concentrated on a rotary evaporator, and the obtained residue was purified by silica gel column chromatography to obtain 20.2 g of compound (VIII-1) (yield 95%). The total yield from hydrazine monohydrate to compound (VIII-1) was 88%.

<Manufacturing example 3>
Compound (VIII-1) was synthesized according to the following scheme.

Compound (II-1) was synthesized in the same manner as in Production Example 1.
Next, 100.1 g of compound (II-1), 180 g of naphthalene-1,5-disulfonic acid tetrahydrate, and 230 mL of methanol were placed in a three-necked flask and stirred at 40 ° C. for 2 hours. After concentrating this with a rotary evaporator, 500 mL of ethyl acetate was added to disperse the crystals, and then the crystals were filtered and dried to obtain 190.3 g of the compound (IV-21) (yield 88%). The total yield from hydrazine monohydrate to compound (IV-21) was 81%.
Next, a Dean Stark condenser was attached to a three-necked flask, 43.3 g of compound (IV-21), 433 mL of xylene, and 26.4 g of dimethyl malonate were added, and a distillation product containing water and the like accumulated in the Dean Stark condenser. The mixture was stirred under heating and reflux for 6 hours. On the way, the same amount of xylene as the extracted distillate was added. Then, the reaction mixture was cooled to 120 ° C., 240 mL of water was added dropwise, and the mixture was stirred under heating under reflux for 1 hour. This was cooled to room temperature, 240 mL of water was added, and the mixture was extracted. The obtained aqueous phase was neutralized with an aqueous sodium hydroxide solution, and then extracted with 240 mL of toluene. The obtained toluene phase and the xylene phase obtained in the previous extraction were combined and washed with 240 mL of 0.02 mol / L hydrochloric acid, and then in an aqueous solution prepared by dissolving 4.2 g of sodium hydrogen carbonate and 76 g of salt in 440 mL of water. After washing, 76 g of sodium chloride was washed with an aqueous solution dissolved in 440 mL of water. Then, the mixture was concentrated on a rotary evaporator, and the obtained residue was purified by silica gel column chromatography to obtain 17.2 g of compound (VIII-1) (yield 81%). The total yield from hydrazine monohydrate to compound (VIII-1) was 66%.

<Manufacturing example 4>
Compound (VIII-18) was synthesized according to the following scheme.

Compound (2) was synthesized in the same manner as in Production Example 1.
Next, 88.07 g of compound (2), 414.6 g of potassium carbonate, and 600 mL of N-methylpyrrolidone were placed in a three-necked flask, and 463.5 g of n-octyl bromide was added dropwise at an internal temperature of 80 ° C. After the dropping, the mixture was heated and stirred as it was for 4 hours, cooled, and 1000 mL of ethyl acetate and 1000 mL of water were added and stirred, and extraction was performed. The obtained ethyl acetate phase was washed 3 times with an aqueous solution consisting of 1000 mL of water and 20.0 g of salt, and then concentrated with a rotary evaporator to obtain 306.3 g of compound (II-20) (yield 98%). ).
Next, 156.3 g of compound (II-20), 190.2 g of p-toluenesulfonic acid monohydrate, and 500 mL of methanol were placed in a three-necked flask and stirred by heating at 50 ° C. for 3 hours. After concentrating this with a rotary evaporator, 1000 mL of acetonitrile was added to disperse the crystals, and then the crystals were filtered and dried to obtain 297.5 g of the compound (I-12) (yield 99%). The total yield from hydrazine monohydrate to compound (I-12) was 93%.
Next, a Dean Stark condenser was attached to a three-necked flask, 60.1 g of compound (I-12), 500 mL of xylene, and 32.0 g of diethyl malonate were added, and a distillation product containing water and the like accumulated in the Dean Stark condenser. The mixture was stirred under heating and reflux for 8 hours. On the way, the same amount of xylene as the extracted distillate was added. Then, the reaction mixture was cooled to 90 ° C., 200 mL of water was added dropwise, and the mixture was stirred at an internal temperature of 90 to 100 ° C. for 1 hour. This was cooled to room temperature, 300 mL of water was added, and the mixture was extracted. The obtained aqueous phase was neutralized with an aqueous sodium hydroxide solution, and then extracted with 300 mL of toluene. The obtained toluene phase and the xylene phase obtained in the previous extraction were combined and washed with 500 mL of 0.02 mol / L hydrochloric acid, and then washed with an aqueous solution of 7.0 g of sodium hydrogen carbonate and 100 g of sodium chloride dissolved in 700 mL of water. Then, 100 g of sodium chloride was washed with an aqueous solution dissolved in 700 mL of water. Then, the mixture was concentrated on a rotary evaporator, and the obtained residue was purified by silica gel column chromatography to obtain 31.8 g of compound (VIII-18) (yield 98%). The total yield from hydrazine monohydrate to compound (VIII-18) was 91%.

<Manufacturing example 5>
Compound (VIII-18) was synthesized according to the following scheme.

Compound (II-20) was synthesized in the same manner as in Production Example 4.
156.3 g of compound (II-20), 180.0 g of naphthalene-1,5-disulfonic acid tetrahydrate, and 500 mL of methanol were placed in a three-necked flask and stirred by heating at 50 ° C. for 3 hours. After concentrating this with a rotary evaporator, 1000 mL of acetonitrile was added to disperse the crystals, and then the crystals were filtered and dried to obtain 237.0 g of the compound (IV-22) (yield 87%). The total yield from hydrazine monohydrate to compound (IV-22) was 82%.
Next, a Dean Stark condenser was attached to a three-necked flask, 54.5 g of compound (IV-22), 500 mL of xylene, and 32.0 g of diethyl malonate were added, and a distillation product containing water and the like accumulated in the Dean Stark condenser. The mixture was stirred under heating and reflux for 8 hours. On the way, the same amount of xylene as the extracted distillate was added. Then, the reaction mixture was cooled to 90 ° C., 200 mL of water was added dropwise, and the mixture was stirred at an internal temperature of 90 to 100 ° C. for 1 hour. This was cooled to room temperature, 300 mL of water was added, and the mixture was extracted. The obtained aqueous phase was neutralized with an aqueous sodium hydroxide solution, and then extracted with 300 mL of toluene. The obtained toluene phase and the xylene phase obtained in the previous extraction were combined and washed with 500 mL of 0.02 mol / L hydrochloric acid, and then washed with an aqueous solution of 7.0 g of sodium hydrogen carbonate and 100 g of sodium chloride dissolved in 700 mL of water. Then, 100 g of sodium chloride was washed with an aqueous solution dissolved in 700 mL of water. Then, the mixture was concentrated on a rotary evaporator, and the obtained residue was purified by silica gel column chromatography to obtain 26.7 g of compound (VIII-18) (yield 82%). The total yield from hydrazine monohydrate to compound (VIII-18) was 67%.

<Manufacturing example 6>
Compound (VIII-9) was synthesized according to the following scheme.

Compound (2) was synthesized in the same manner as in Production Example 1.
Next, 88.07 g of compound (2), 414.6 g of potassium carbonate, and 600 mL of N-methylpyrrolidone were placed in a three-necked flask, and 412.9 g of n-hexyl bromide was added dropwise at an internal temperature of 80 ° C. After the dropping, the mixture was heated and stirred as it was for 4 hours, cooled, and 1000 mL of ethyl acetate and 1000 mL of water were added and stirred, and extraction was performed. The obtained ethyl acetate phase was washed 3 times with an aqueous solution consisting of 1000 mL of water and 20.0 g of salt, and then concentrated with a rotary evaporator to obtain 253.9 g of compound (II-5) (yield 99%). ).
Next, 128.2 g of compound (II-5), 190.2 g of p-toluenesulfonic acid monohydrate, and 500 mL of methanol were placed in a three-necked flask and stirred by heating at 45 ° C. for 3 hours. After concentrating this with a rotary evaporator, 1000 mL of ethyl acetate was added to disperse the crystals, and then the crystals were filtered and dried to obtain 269.8 g of compound (I-4) (yield 99%). The total yield from hydrazine monohydrate to compound (I-4) was 94%.
Next, a Dean Stark condenser was attached to a three-necked flask, 54.5 g of compound (I-4), 500 mL of xylene, and 26.4 g of dimethyl malonate were added, and a distillation product containing water and the like accumulated in the Dean Stark condenser. The mixture was stirred under heating and reflux for 8 hours. On the way, the same amount of xylene as the extracted distillate was added. Then, the reaction mixture was cooled to 90 ° C., 200 mL of water was added dropwise, and the mixture was stirred at an internal temperature of 90 to 100 ° C. for 1 hour. This was cooled to room temperature, 300 mL of water was added, and the mixture was extracted. The obtained aqueous phase was neutralized with an aqueous sodium hydroxide solution, and then extracted with 300 mL of toluene. The obtained toluene phase and the xylene phase obtained in the previous extraction were combined and washed with 500 mL of 0.02 mol / L hydrochloric acid, and then washed with an aqueous solution of 7.0 g of sodium hydrogen carbonate and 100 g of sodium chloride dissolved in 700 mL of water. Then, 100 g of sodium chloride was washed with an aqueous solution dissolved in 700 mL of water. Then, the mixture was concentrated on a rotary evaporator, and the obtained residue was purified by silica gel column chromatography to obtain 26.0 g of compound (VIII-9) (yield 97%). The total yield from hydrazine monohydrate to compound (VIII-9) was 91%.

<Manufacturing example 7>
Compound (VIII-9) was synthesized according to the following scheme.

Compound (II-5) was synthesized in the same manner as in Production Example 6.
Next, 128.2 g of compound (II-5), 180 g of naphthalene disulfonic acid tetrahydrate, and 500 mL of methanol were placed in a three-necked flask and stirred by heating at 45 ° C. for 3 hours. After concentrating this with a rotary evaporator, 1000 mL of ethyl acetate was added to disperse the crystals, and then the crystals were filtered and dried to obtain 217.5 g of the compound (IV-23) (yield 89%). The total yield from hydrazine monohydrate to compound (IV-23) was 85%.
Next, a Dean Stark condenser was attached to a three-necked flask, 48.9 g of compound (IV-23), 500 mL of xylene, and 26.4 g of dimethyl malonate were added, and the distilled product containing water and the like accumulated in the Dean Stark condenser was added. While removing the mixture, the mixture was stirred under heating and reflux for 8 hours. On the way, the same amount of xylene as the extracted distillate was added. Then, the reaction mixture was cooled to 90 ° C., 200 mL of water was added dropwise, and the mixture was stirred at an internal temperature of 90 to 100 ° C. for 1 hour. This was cooled to room temperature, 300 mL of water was added, and the mixture was extracted. The obtained aqueous phase was neutralized with an aqueous sodium hydroxide solution, and then extracted with 300 mL of toluene. The obtained toluene phase and the xylene phase obtained in the previous extraction were combined and washed with 500 mL of 0.02 mol / L hydrochloric acid, and then with an aqueous solution prepared by dissolving 7.0 g of sodium hydrogen carbonate and 100 g of salt in 700 mL of water. After washing, it was washed with an aqueous solution in which 100 g of sodium chloride was dissolved in 700 mL of water. Then, the mixture was concentrated on a rotary evaporator, and the obtained residue was purified by silica gel column chromatography to obtain 21.7 g of compound (VIII-9) (yield 81%). The total yield from hydrazine monohydrate to compound (VIII-9) was 69%.

<Manufacturing example 8>
Compound (VIII-2) was synthesized according to the following scheme.

Compound (2) was synthesized in the same manner as in Production Example 1.
Next, 88.07 g of compound (2), 414.6 g of potassium carbonate, 133 mL of N, N-dimethylacetamide and 317 mL of acetonitrile were placed in a three-necked flask, and 463.5 g of 2-ethylhexyl bromide was added dropwise under heating under reflux. After the dropping, the mixture was heated under reflux for 3 hours as it was, cooled, 1000 mL of ethyl acetate and 1000 mL of water were added, and the mixture was stirred and extracted. The obtained ethyl acetate phase was washed 3 times with a saline solution prepared from 14.5 g of salt and 1,000 mL of water, and then concentrated with a rotary evaporator to obtain 297.0 g of compound (II-2) as a residue. Obtained (yield 95%).
Next, 31.3 g of compound (II-2), 38.1 g of p-toluenesulfonic acid monohydrate, and 90 mL of methanol were placed in a three-necked flask and stirred at 40 ° C. for 2 hours. After concentrating this with a rotary evaporator, 500 mL of ethyl acetate was added to disperse the crystals, and then the crystals were filtered and dried to obtain 55.3 g of compound (I-2) (yield 92%). The total yield from hydrazine monohydrate to compound (I-2) was 84%.
Next, a Dean Stark condenser was attached to a three-necked flask, 60.1 g of compound (I-2), 400 mL of xylene, and 26.4 g of dimethyl malonate were added, and a distillation product containing water and the like accumulated in the Dean Stark condenser. The mixture was stirred under heating and reflux for 6 hours. On the way, the same amount of xylene as the extracted distillate was added. Then, the reaction mixture was cooled to 120 ° C., 250 mL of water was added dropwise, and the mixture was stirred under heating under reflux for 1 hour. This was cooled to room temperature, 250 mL of water was added, and the mixture was extracted. The obtained aqueous phase was neutralized with an aqueous sodium hydroxide solution, and then extracted with 400 mL of toluene. The obtained toluene phase and the xylene phase obtained in the previous extraction were combined and washed with 800 mL of 0.02 mol / L hydrochloric acid, and then washed with an aqueous solution prepared by dissolving 6 g of sodium hydrogen carbonate and 100 g of sodium chloride in 700 mL of water. Then, 100 g of sodium chloride was washed with an aqueous solution dissolved in 700 mL of water. Then, the mixture was concentrated on a rotary evaporator, and the obtained residue was purified by silica gel column chromatography to obtain 29.9 g of compound (VIII-2) (yield 92%). The total yield from hydrazine monohydrate to compound (VIII-2) was 77%.

<Manufacturing example 9>
Compound (VIII-2) was synthesized according to the following scheme.

Compound (II-2) was synthesized in the same manner as in Production Example 8.
Then, 31.3 g of compound (II-2), 19.2 g of methanesulfonic acid, and 90 mL of methanol were placed in a three-necked flask and heated and stirred at 40 ° C. for 2 hours. After concentrating this with a rotary evaporator, 500 mL of ethyl acetate was added to disperse the crystals, and then the crystals were filtered and dried to obtain 41.7 g of compound (I-11) (yield 93%). The total yield from hydrazine monohydrate to compound (I-11) was 85%.
Next, a Dean Stark condenser was attached to a three-necked flask, 44.8 g of compound (I-11), 400 mL of xylene, and 26.4 g of dimethyl malonate were added, and a distillation product containing water and the like accumulated in the Dean Stark condenser. The mixture was stirred under heating and reflux for 6 hours. On the way, the same amount of xylene as the extracted distillate was added. Then, the reaction mixture was cooled to 120 ° C., 250 mL of water was added dropwise, and the mixture was stirred under heating under reflux for 1 hour. This was cooled to room temperature, 250 mL of water was added, and the mixture was extracted. The obtained aqueous phase was neutralized with an aqueous sodium hydroxide solution, and then extracted with 400 mL of toluene. The obtained toluene phase and the xylene phase obtained in the previous extraction were combined and washed with 800 mL of 0.02 mol / L hydrochloric acid, and then washed with an aqueous solution prepared by dissolving 6 g of sodium hydrogen carbonate and 100 g of sodium chloride in 700 mL of water. Then, 100 g of sodium chloride was washed with an aqueous solution dissolved in 700 mL of water. Then, the mixture was concentrated on a rotary evaporator, and the obtained residue was purified by silica gel column chromatography to obtain 29.5 g of compound (VIII-2) (yield 91%). The total yield from hydrazine monohydrate to compound (VIII-2) was 77%.

<Manufacturing example 10>
Compound (VIII-2) was synthesized according to the following scheme.

Compound (II-2) was synthesized in the same manner as in Production Example 8.
Next, 31.3 g of compound (II-2), 38.0 g of p-toluenesulfonic acid monohydrate, and 90 mL of methanol were placed in a three-necked flask and stirred at 40 ° C. for 2 hours. After concentrating this with a rotary evaporator, 500 mL of ethyl acetate was added to disperse the crystals, and then the crystals were filtered and dried to obtain 45.8 g of the compound (IV-20) (yield 84%). The total yield from hydrazine monohydrate to compound (IV-20) was 77%.
Next, a Dean Stark condenser was attached to a three-necked flask, 54.5 g of compound (IV-20), 400 mL of xylene, and 26.4 g of dimethyl malonate were added, and a distillation product containing water and the like accumulated in the Dean Stark condenser. The mixture was stirred under heating and reflux for 6 hours. On the way, the same amount of xylene as the extracted distillate was added. Then, the reaction mixture was cooled to 120 ° C., 250 mL of water was added dropwise, and the mixture was stirred under heating under reflux for 1 hour. This was cooled to room temperature, 250 mL of water was added, and the mixture was extracted. The obtained aqueous phase was neutralized with an aqueous sodium hydroxide solution, and then extracted with 400 mL of toluene. The obtained toluene phase and the xylene phase obtained in the previous extraction were combined and washed with 800 mL of 0.02 mol / L hydrochloric acid, and then washed with an aqueous solution prepared by dissolving 6 g of sodium hydrogen carbonate and 100 g of sodium chloride in 700 mL of water. Then, 100 g of sodium chloride was washed with an aqueous solution dissolved in 700 mL of water. Then, it concentrated with a rotary evaporator to obtain 26.9 g of the target compound (VIII-2) (yield 83%). The total yield from hydrazine monohydrate to compound (VIII-2) was 64%.

<Manufacturing example 11>
Compound (VI-2) was synthesized according to the following scheme.

Compound (2) was synthesized in the same manner as in Production Example 1.
Next, 88.07 g of compound (2), 414.6 g of potassium carbonate, and 600 mL of N-methylpyrrolidone were placed in a three-necked flask, and 376.3 g of benzyl bromide was added dropwise at an internal temperature of 70 ° C. After the dropping, the mixture was heated and stirred as it was for 2 hours, cooled, and 1000 mL of ethyl acetate and 1000 mL of water were added and stirred, and extraction was performed. The obtained ethyl acetate phase was washed 3 times with 1000 mL of water and then concentrated on a rotary evaporator to obtain 269 g of compound (II-6) as a residue (yield 100%).
Next, 26.8 g of compound (II-6), 31.6 g of benzenesulfonic acid, and 200 mL of isopropyl alcohol were placed in a three-necked flask and stirred by heating at 60 ° C. for 3 hours. After concentrating this with a rotary evaporator, 500 mL of acetonitrile was added to disperse the crystals, and then the crystals were filtered and dried to obtain 49.2 g of compound (I-6) (yield 93%). The total yield from hydrazine monohydrate to compound (I-6) was 89%.
Next, a Dean Stark condenser was attached to a three-necked flask, 49.2 g of compound (I-6), 400 mL of xylene, and 68.1 g of methyl benzoate were added, and a distillation product containing water and the like accumulated in the Dean Stark condenser. The mixture was stirred under heating and reflux for 8 hours. On the way, the same amount of xylene as the extracted distillate was added. Then, the reaction mixture was cooled to 90 ° C., 600 mL of water was added dropwise, and the mixture was stirred at an internal temperature of 90 to 100 ° C. for 1 hour. This was cooled to room temperature, 600 mL of water was added, and the mixture was extracted. The obtained aqueous phase was neutralized with an aqueous sodium hydroxide solution, and then extracted with 600 mL of toluene. The obtained toluene phase and the xylene phase obtained in the previous extraction were combined and washed with 1.21 L of 0.02 mol / L hydrochloric acid, and then 12.9 g of sodium hydrogen carbonate and 232 g of salt were dissolved in 1.21 L of water. Then, 232 g of sodium chloride was washed with an aqueous solution dissolved in 1.21 L of water. Then, the mixture was concentrated on a rotary evaporator, and the obtained residue was purified by silica gel column chromatography to obtain 35.2 g of compound (VI-2) (yield 90%). The total yield from hydrazine monohydrate to compound (VI-2) was 80%.

<Manufacturing example 12>
Compound (IV-20) was synthesized according to the method described in Example 3 of JP-A-2010-018595.
That is, 900 mL of ethanol was added to 46.2 g (0.92 mol) of hydrazine monohydrate and stirred under ice-cooling (internal temperature 0 ° C. or lower), and then 236.7 g (1.) of 2-ethylhexanal was added thereto. A mixed solution prepared by dissolving 84 mol) in 600 mL of ethanol was added dropwise over 30 minutes (internal temperature 2 to 5 ° C.). After stirring this reaction solution at room temperature for 2 hours, ethanol was added so that the total amount of the reaction solution became 2.0 L to prepare an ethanol solution of compound (E-6).
110 mL of an ethanol solution (theoretical molar number of 50 mmol) of the prepared compound (E-6), 10 mL of ethanol, and 1.0 g of a lane nickel catalyst were added to an autoclave, filled with hydrogen until the pressure reached 40 atm, and at 80 ° C. for 5 hours. Stirred. After cooling the reaction solution with air, the catalyst was removed by filtration through Celite to prepare an ethanol solution of compound (D-6). After adding 19.8 g (55 mmol) of naphthalene 1,5-disulfonic acid tetrahydrate to this ethanol solution, ethanol was concentrated under reduced pressure to make the total volume about 100 mL, and 200 mL of acetonitrile was further added to precipitate crystals. .. After stirring at room temperature for 30 minutes, the crystals were collected by filtration and dried to obtain 14.9 g of compound (IV-20). The total yield from hydrazine monohydrate to compound (IV-20) was 56%.

The yields of the compounds obtained in each step of Production Examples 1 to 12 are summarized in the table below.

Production Examples 1 to 11 are production examples corresponding to the examples of the present invention, and Production Example 12 is a production example corresponding to a comparative example with respect to the present invention.
As is clear from the above table, in Production Examples 1, 3 to 11, the total yield of the compound (I) or the compound (IV) from the hydrazine monohydrate was significantly higher than that of the production example 12, and the yield of the compound was significantly higher. The rate was remarkably excellent.
In Production Example 2, since the compound (VIII-1) was synthesized without taking out the compound (I-1), the yield of the compound (I-1) was not calculated, but the compound (Final product) was obtained. Since the total yield of hydrazine monohydrate of VIII-1) was the same as that of Production Example 1, the yield of compound (I-1) in Production Example 2 was as high as that of Production Example 1. It can be understood that it is a rate.
Further, in Production Examples 1 to 11, since the compound (I) or the compound (IV) could be produced without going through the step of synthesizing the neutral hydrazine compound, the safety at the time of producing the compound was excellent.

(Evaluation of heat generation start temperature)
The heat generation start temperature in the differential scanning calorimetry of compounds (I-1), (IV-21), (R-1), and (R-2) was measured. The heat generation start temperature of compound (I-1) is 233 ° C., the heat generation start temperature of compound (IV-21) is 223 ° C., the heat generation start temperature of compound (R-1) is 56 ° C., and the heat generation start temperature of compound (R-2) is 56 ° C. The heat generation start temperature of) was 85 ° C. Compound (I-1) is a compound corresponding to an example of the present invention, and this compound has a higher heat generation start temperature than compounds (IV-21), (R-1), and (R-2) and is more stable. It was a compound.

Claims (5)

A method for producing a compound represented by the formula (IV), which comprises reacting a compound represented by the formula (II) with a compound represented by the formula (III);

In the formula, R ²¹ , R ²² and R ³¹ independently represent an aliphatic group, an aromatic group or a heterocyclic group, respectively.
m represents a positive integer, q represents a positive number,
R ²¹ and R ²² may be combined with each other to form a ring. The compound according to claim 1, wherein the ratio of the product of the number of moles of the compound represented by the formula (III) to the number of m to the number of moles of the compound represented by the formula (II) is 1.0 or more. Manufacturing method. The method for producing a compound according to claim 1 or 2, wherein the compound represented by the formula (IV) is a compound represented by the formula (I);

In the formula, R ²¹ , R ²² and R ³² each independently represent an aliphatic group, an aromatic group or a heterocyclic group, p represents a positive number, and R ²¹ and R ²² combine with each other to form a ring. May be. After obtaining the compound represented by the formula (IV) by the method for producing the compound according to any one of claims 1 to 3, the compound represented by the formula (IV) and the compound represented by the formula (V) are obtained. A method for producing a compound represented by the formula (VI), which comprises reacting;

In the formula, R ²¹ , R ²² , R ³¹ , R ⁵¹ and R ⁵² independently represent an aliphatic group, an aromatic group or a heterocyclic group, m represents a positive integer, q represents a positive number, and so on. R ²¹ and R ²² may be combined with each other to form a ring. After obtaining the compound represented by the formula (IV) by the method for producing the compound according to any one of claims 1 to 3, the compound represented by the formula (IV) and the compound represented by the formula (VII) are obtained. A method for producing a compound represented by the formula (VIII), which comprises reacting;

In the formula, R ²¹ , R ²² , R ³¹ and R ⁷¹ each independently represent an aliphatic group, an aromatic group or a heterocyclic group, L ⁷¹ represents a divalent linking group, and m represents a positive integer. , Q represent a positive number, and R ²¹ and R ²² may be combined with each other to form a ring.