JP2021107388A - Method for producing hydroxyalkylcarboxamide compound and hydroxyalkylcarboxamide compound - Google Patents

Abstract

To provide a method for producing a hydroxyalkylcarboxamide compound that can produce a compound having a block isocyanato group and a hydroxy group without using a compound including halogen.SOLUTION: The method for producing a hydroxyalkylcarboxamide compound includes a first step of synthesizing a compound by reacting either one or both of a carbamic acid ester and a cyclized product of a carbamic acid ester with a blocking agent including a pyrazole ring in the presence of a solvent.SELECTED DRAWING: None

Description

The present invention relates to a method for producing a hydroxyalkylcarboxamide compound having a blocked isocyanate group and a hydroxy group, and a hydroxyalkylcarboxamide compound.

Among the carbamic acid esters, those generally called blocked isocyanates are synthesized by a method of reacting isocyanate with an isocyanato group (-NCO) blocking agent. Conventionally, as a blocking agent for an isocyanato group, compounds such as pyrazoles and ketooximes that add active hydrogen to an isocyanato group have been used. When the carbamic acid ester obtained from pyrazoles or ketooximes is heated, the blocking agent is dissociated and the isocyanato group is regenerated to become an isocyanate. Such carbamic acid esters are widely used as compounds having a blocked isocyanate group in which the isocyanate group is protected by a blocking agent.

As a compound having a block isocyanate group, a highly versatile compound that can be used as a material for various compounds is required. Examples of such a compound include compounds having a blocked isocyanate group and a hydroxy group in the molecule.
Compounds having a block isocyanate group and a hydroxy group can undergo various reactions using a hydroxy group and can be reacted with various compounds. Moreover, the compound having a blocking isocyanate group and a hydroxy group can self-polymerize because a urethane bond (-NH-CO-O-) can be formed by dissociating the blocking agent.

As a method for synthesizing a compound having a block isocyanate group and a hydroxy group, for example, there are the methods described in Patent Document 1 and Patent Document 2. Patent Document 1 and Patent Document 2 describe a method for synthesizing a compound having a blocked isocyanate group and a hydroxy group using a phosgene or a chloroformic acid compound as a raw material.

German Patent Application Publication No. 102013021933 German Patent Application Publication No. 1618361

However, in the method for producing a compound having a blocked isocyanate group and a hydroxy group described in Patent Document 1 and Patent Document 2, a phosgene or a chloroformic acid compound is used as a raw material. Phosgene and chloroformic acid are toxic substances and are difficult to handle. The phosgene and chloroformic acid compounds are compounds containing halogen. If a compound containing a halogen remains as an impurity in a compound used for an electronic component, the electronic component may be hindered. Therefore, it is desirable not to use halogen-containing compounds as raw materials for compounds used in electronic components.

Further, as a method for synthesizing a compound having a blocked isocyanato group and a hydroxy group without using a compound containing a halogen, a method of synthesizing an isocyanate having a hydroxy group and protecting the isocyanato group with a blocking agent is used. Can be considered.

However, the isocyanato group is highly reactive with the hydroxy group. For this reason, it is difficult to have both an isocyanato group and a hydroxy group present in the compound. Further, the reactivity of the isocyanato group and the hydroxy group is higher than the reactivity of the isocyanato group and the active hydrogen of the blocking agent. From these facts, it is difficult to synthesize a blocked isocyanate group and a compound having a hydroxy group by using a method of synthesizing an isocyanate having a hydroxy group and protecting the isocyanato group with a blocking agent.

Therefore, in the conventional technique, it has been difficult to synthesize a compound having a blocked isocyanate group and a hydroxy group without using a compound containing a halogen.
Further, a novel hydroxyalkylcarboxamide compound which has a block isocyanate group and a hydroxy group and can be produced without using a halogen-containing compound has been desired.

The present invention has been made in view of the above circumstances, and is a method for producing a hydroxyalkylcarboxamide compound for synthesizing a hydroxyalkylcarboxamide compound having a blocked isocyanate group and a hydroxy group without using a compound containing a halogen, and a hydroxy. It is an object of the present invention to provide an alkylcarboxamide compound.

The present inventors have diligently studied to solve the above problems.
As a result, by reacting a specific carbamic acid ester (and / or a cyclized product thereof) with a specific blocking agent in the presence of a solvent, the hydroxyalkylcarboxamide compound can be obtained without using a compound containing a halogen. We found that it could be obtained and came up with the present invention.
That is, the present invention relates to the following matters.

[1] In the presence of a solvent, one or both of the carbamic acid ester represented by the following general formula (3) and the cyclized compound of the carbamic acid ester represented by the following general formula (4), and the following general formula ( A method for producing a hydroxyalkyl carboxamide compound, which comprises a first step of synthesizing a compound represented by the following general formula (6) by reacting with a blocking agent containing a pyrazole ring represented by 5).

（式（３）において、Ｒ^１は−ＣＨ_３、−ＣＨ_２−ＣＨ_３を示す。式（３）、式（４）および式（６）において、Ｒ^２は炭素原子数２〜６の直鎖状アルキレン基または炭素原子数４〜６のシクロアルキレン基を示す。式（５）および式（６）において、Ｒ^３およびＲ^５はそれぞれ−Ｈ、−ＣＨ_３または−ＣＨ_２−ＣＨ_３のいずれかを示し、Ｒ^４は−Ｈを示す。式（５）において、Ｘは水素原子、アルカリ金属原子のいずれかを示す。）

(In the formula (3), R ¹ represents -CH ₃ and -CH _2- CH _{3. In the} formulas (3), (4) and (6), R ² is a direct number of carbon atoms 2 to 6. Indicates a chain alkylene group or a cycloalkylene group having 4 to 6 carbon atoms. In formulas (5) and (6), R ³ and R ⁵ are of −H, −CH ₃ or −CH ₂ −CH ₃ , respectively. Either is indicated, and R ⁴ indicates −H. In the formula (5), X indicates either a hydrogen atom or an alkali metal atom.)

[2] Before the first step,
By reacting the dialkyl carbonate represented by the following general formula (1) with the compound having an amino group and a hydroxy group represented by the following general formula (2), the carbamic acid ester represented by the following general formula (3) can be obtained. The method for producing a hydroxyalkyl carboxamide compound according to [1], which comprises performing a second step of synthesizing one or both of the cyclized compounds of the carbamic acid ester represented by the following general formula (4).

（式（１）および式（３）において、Ｒ^１は−ＣＨ_３、−ＣＨ_２−ＣＨ_３を示す。式（１）中の２つのＲ^１は同じである。式（２）〜式（４）において、Ｒ^２は炭素原子数２〜６の直鎖状アルキレン基または炭素原子数４〜６のシクロアルキレン基を示す。）

(In the formula (1) and (3), ^{R 1} is _{-CH 3,} 2 one of ^{R 1} are shown a -CH 2 -CH _3. Equation (1) is the same. Equation (2) to ( In 4), R ² represents a linear alkylene group having 2 to 6 carbon atoms or a cycloalkylene group having 4 to 6 carbon atoms.)

[3] In the formula (3), R ¹ represents −CH ₃ , and in the formulas (3), (4) and (6), R ² represents −CH ₂ −CH ₂ −, and the formula (5). ) And the method for producing a hydroxyalkylcarboxamide compound according to [1] or [2] ^{, wherein R 3} and R ⁵ represent −CH ₃ and R ⁴ represents −H in the formula (6).

[4] The first step is characterized in that one or both of the carbamic acid ester and the cyclized product is reacted with the blocking agent in the presence of an activator composed of a basic compound. The method for producing a hydroxyalkylcarboxamide compound according to any one of [1] to [3].

[5] The activator is selected from alkali metal hydrides, alkaline earth metal hydrides, primary to tertiary alkoxides, alkali metal hydroxides, and alkali metal phosphates. The method for producing a hydroxyalkylcarboxamide compound according to [4], which comprises one kind or two or more kinds.
[6] The method for producing a hydroxyalkylcarboxamide compound according to [4], wherein the activator is any one selected from lithium methoxide, sodium methoxide, and sodium tert-butoxide.

[7] In the first step, one or both of the carbamic acid ester and the cyclized compound are reacted with the blocking agent in an amide-based solvent [1] to [1] to [ 6] The method for producing a hydroxyalkylcarboxamide compound according to any one of.
[8] The method for producing a hydroxyalkylcarboxamide compound according to [7], wherein the amide-based solvent is N, N-dimethylformamide.

[9] A hydroxyalkylcarboxamide compound represented by the following general formula (60).

（式（６０）において、Ｒ^２０は−ＣＨ_２−ＣＨ_２−ＣＨ_２−を示す。Ｒ^３０およびＲ^５０はそれぞれ−Ｈ、−ＣＨ_３または−ＣＨ_２−ＣＨ_３のいずれかを示し、Ｒ^４０は−Ｈを示す。）

(In formula (60), R ²⁰ represents −CH ₂ −CH ₂ −CH ₂ −. R ³⁰ and R ⁵⁰ represent either −H, −CH ₃ or −CH ₂ −CH ₃ , respectively, and R ⁴⁰ indicates -H.)

According to the method for producing a hydroxyalkylcarboxamide compound of the present invention, a hydroxyalkylcarboxamide compound having a blocked isocyanate group and a hydroxy group can be produced without using a compound containing a halogen.
According to the present invention, it is possible to provide a novel hydroxyalkylcarboxamide compound having a blocked isocyanate group and a hydroxy group.

FIG. 1 is a ¹ H-NMR measurement chart of Example 1. FIG. 2 is a ¹³ C-NMR measurement chart of Example 1. FIG. 3 is a ¹ H-NMR measurement chart of Example 28. FIG. 4 is a ¹³ C-NMR measurement chart of Example 28. FIG. 5 is a ¹ H-NMR measurement chart of Example 29. FIG. 6 is a ¹³ C-NMR measurement chart of Example 29.

Hereinafter, the method for producing the compound of the present invention will be described in detail. The present invention is not limited to the embodiments shown below.

<Compound manufacturing method>
The method for producing the hydroxyalkyl carboxamide compound of the present embodiment includes a carbamic acid ester synthesis step (corresponding to the "second step" in the claims) and a carboxamide compound synthesis step (the "first step" in the claims. ”.) And is included.

The carbamic acid ester synthesis step can be, for example, the step shown below. First, the dialkyl carbonate represented by the following general formula (1) is reacted with a compound having an amino group and a hydroxy group represented by the following general formula (2). As a result, either or both of the carbamic acid ester represented by the following general formula (3) and the cyclized product of the carbamic acid ester represented by the following general formula (4) are synthesized.

（式（１）および式（３）において、Ｒ^１は−ＣＨ_３、−ＣＨ_２−ＣＨ_３を示す。式（１）中の２つのＲ^１は同じである。式（２）〜式（４）において、Ｒ^２は炭素原子数２〜６の直鎖状アルキレン基または炭素原子数４〜６のシクロアルキレン基を示す。）

(In the formula (1) and (3), ^{R 1} is _{-CH 3,} 2 one of ^{R 1} are shown a -CH 2 -CH _3. Equation (1) is the same. Equation (2) to ( In 4), R ² represents a linear alkylene group having 2 to 6 carbon atoms or a cycloalkylene group having 4 to 6 carbon atoms.)

In the carboxamide compound synthesis step, in the presence of a solvent, one or both of the carbamic acid ester represented by the formula (3) and the cyclized product represented by the formula (4) are represented by the following general formula (5). React with a blocking agent containing a pyrazole ring. As a result, the hydroxyalkylcarboxamide compound represented by the following general formula (6) is synthesized.

（式（３）において、Ｒ^１は−ＣＨ_３、−ＣＨ_２−ＣＨ_３を示す。式（３）、式（４）および式（６）において、Ｒ^２は炭素原子数２〜６の直鎖状アルキレン基または炭素原子数４〜６のシクロアルキレン基を示す。式（５）および式（６）において、Ｒ^３およびＲ^５はそれぞれ−Ｈ、−ＣＨ_３または−ＣＨ_２−ＣＨ_３のいずれかを示し、Ｒ^４は−Ｈを示す。式（５）において、Ｘは水素原子、アルカリ金属原子のいずれかを示す。）

(In the formula (3), R ¹ represents -CH ₃ and -CH _2- CH _{3. In the} formulas (3), (4) and (6), R ² is a direct number of carbon atoms 2 to 6. Indicates a chain alkylene group or a cycloalkylene group having 4 to 6 carbon atoms. In formulas (5) and (6), R ³ and R ⁵ are of −H, −CH ₃ or −CH ₂ −CH ₃ , respectively. Either is indicated, and R ⁴ indicates −H. In the formula (5), X indicates either a hydrogen atom or an alkali metal atom.)

(Carbamic acid ester synthesis step)
In carbamate synthesis step, dialkyl carbonate represented by formula is used as a raw material (1) has the formula (1) two in R ¹ are both dimethyl carbonate or formula (1) in a -CH ₃ least two of ^{R 1} both are diethyl carbonate is _-CH 2 -CH _3, is preferably dimethyl carbonate. When the dialkyl carbonate represented by the formula (1) is a dimethyl carbonate, the product desorbed from the raw material with the synthesis of the hydroxyalkylcarboxamide compound represented by the general formula (6) is methanol. Since methanol is a compound having a low boiling point, it is easy to separate from the reaction product and is preferable.

In the carbamic acid ester synthesis step, the compound having an amino group and a hydroxy group represented by the formula (2) used as a raw material has a ^{linear alkylene group in which R 2} in the formula (2) has 2 to 6 carbon atoms. Alternatively, it is a cycloalkylene group having 4 to 6 carbon atoms. As the compound having an amino group and a hydroxy group represented by the formula (2), the hydroxyalkylcarboxamide compound represented by the formula (6) has high versatility, and therefore R ² is −CH ₂ −CH ₂ −. It is preferable to use some ethanolamine, or 3-amino-1-propanol in which ^{R 2} is -CH _2- CH _2- CH _2-. When R ² is a cycloalkylene group having 4 to 6 carbon atoms, it is preferably a cyclohexene group.

In the carbamic acid ester synthesis step, the conditions for reacting the dialkyl carbonate represented by the formula (1) with the compound having an amino group and a hydroxy group represented by the formula (2) are the dialkyl carbonate represented by the formula (1). And, it can be appropriately determined according to the type of the compound represented by the formula (2), and is not particularly limited.
For example, when the dialkyl carbonate represented by the formula (1) is a dimethyl carbonate and the compound represented by the formula (2) is ethanolamine, it is preferable to react in a closed container under a solvent-free condition.
In this case, the reaction temperature is preferably in the range of 25 ° C. to 150 ° C., more preferably in the range of 35 ° C. to 120 ° C., further preferably in the range of 50 ° C. to 100 ° C., and 60 to 60 to 100 ° C. The range of 95 ° C. is more preferable, and the range of 70 ° C. to 90 ° C. is particularly preferable. The reaction time is preferably 0.5 hours to 24 hours, more preferably 1 hour to 12 hours, and even more preferably 2 hours to 6 hours.

The reaction for synthesizing either or both of the carbamic acid ester represented by the formula (3) and the cyclized product represented by the formula (4) in the carbamic acid ester synthesis step is carried out in the presence of a catalyst to promote the reaction. You may go.
As catalysts, lithium hydride, sodium hydride, potassium hydride, lithium methoxide, sodium methoxide, potassium methoxide, calcium methoxide, lithium tert-butoxide, sodium tert-butoxide, potassium tert-butoxide, triethylamine, diah Zabicycloundecene, sodium hydroxide, potassium phosphate, sodium phosphate, lithium phosphate and the like can be used. Among these, it is particularly preferable to use sodium methoxide and sodium tert-butoxide in terms of reaction yield.
The content of the catalyst can be, for example, 0.01 to 0.1 molar equivalent with respect to the compound represented by the formula (2).

In the carbamic acid ester synthesis step, one or both of the carbamic acid ester represented by the formula (3) and the cyclized product of the carbamic acid ester represented by the formula (4) are synthesized. In the carbamic acid ester synthesis step, only one of the carbamic acid ester represented by the formula (3) and the cyclized product of the carbamic acid ester represented by the formula (4) may be selectively synthesized. These may be synthesized as a mixture containing them in an arbitrary ratio.

(Carboxamide compound synthesis step)
The blocking agent containing the pyrazole ring represented by the formula (5) used in the carboxamide compound synthesis step has R ³ and R ⁵ in the formula (5) of -H, -CH ₃ , and -CH _2- CH ₃ , respectively. In any of these, R ⁴ indicates −H, and X indicates either a hydrogen atom or an alkali metal atom.
As the blocking agent containing the pyrazole ring represented by the formula (5), those in which ^{R 3} and R ⁵ are −CH _{3 are preferable.} When R ³ and R ⁵ are −CH ₃ , the produced hydroxyalkylcarboxamide compound represented by the formula (6) is easily dissociated from the blocking agent by heating, and the isocyanato group is regenerated. It will be highly sexual.

Further, X in the formula (5) may be a hydrogen atom or an alkali metal atom. When X is an alkali metal atom, the compound represented by the formula (6) can be obtained in a high yield without using an activator. Examples of the alkali metal when X is an alkali metal atom include lithium, sodium, potassium and the like, and sodium is preferable because it is inexpensive and easily available.

One or both of the carbamic acid ester represented by the formula (3) and the cyclized product of the carbamic acid ester represented by the formula (4) used in the carboxamide compound synthesis step, and the blocking represented by the formula (5). The ratio with the agent is 1: 1 in molar ratio (formula (3) (and / or formula (4)): blocking agent) because the hydroxyalkylcarboxamide compound represented by the formula (6) can be obtained in a high yield. It is preferably in the range of 1 to 1:10, and more preferably in the range of 1: 1 to 1: 5.

In the carboxamide compound synthesis step, in the presence of a solvent, one or both of the carbamic acid ester represented by the formula (3) and the cyclized product of the carbamic acid ester represented by the formula (4), and a blocking agent To react. The solvent used in the carboxamide compound synthesis step is preferably a polar solvent having a high boiling point.
Specifically, as the solvent, for example, N, N-dimethylacetamide (DMAc), N, N-dimethylformamide (DMF), N-methyl-2-pyrrolidone (NMP), acetonitrile, formamide, dimethyl sulfoxide (DMSO). , Hexamethylphosphoric acid triamide, anisole, dimethoxyethane, diethylene glycol dimethyl ether and the like can be used. Among these, as the solvent, since the compound represented by the formula (6) can be obtained in a high yield, an amide-based solvent such as N, N-dimethylacetamide, N, N-dimethylformamide, N-methyl-2-pyrrolidone and the like can be obtained. Is preferable, and in particular, it is more preferable to use N, N-dimethylformamide.

The sum of the carbamic acid ester represented by the formula (3) and / or the cyclized compound of the carbamic acid ester represented by the formula (4) and the blocking agent containing the pyrazole ring represented by the formula (5) contained in the solvent. The content is preferably in the range of 0.2 mol / L to 4.0 mol / L, preferably 0.5 mol / L to 1.5 mol / L, because the compound represented by the formula (6) can be obtained in a high yield. It is more preferably in the range of L.

In the carboxamide compound synthesis step, one or both of the carbamic acid ester represented by the formula (3) and the cyclized product of the carbamic acid ester represented by the formula (4) and the pyrazole ring represented by the formula (5) are included. The conditions for synthesizing the compound represented by the formula (6) by reacting with the blocking agent can be appropriately determined according to the type of the target compound represented by the formula (6), the type of solvent used, and the like. , Not particularly limited.

For example, when the hydroxyalkylcarboxamide compound represented by the formula (6) has R ² of −CH ₂ −CH ₂ −, R ³ and R ⁵ of −CH ₃ , and R ⁴ of −H, the following It is preferable that the reaction temperature and reaction time are as shown in.
That is, the reaction temperature is preferably in the range of 100 ° C. to 200 ° C. so as to suppress the formation of 2-oxazolidone, which is a by-product, and obtain a compound represented by the formula (6) in a high yield. More preferably, it is in the range of 130 ° C to 160 ° C.

The reaction time in the carboxamide compound synthesis step is preferably in the range of 3 hours to 20 hours, preferably in the range of 4 hours to 10 hours, because the compound represented by the formula (6) can be obtained in a high yield. More preferred. When the reaction time is 3 to 20 hours, it is possible to suppress the formation of oligomers and / or polymers as by-products, and the productivity is improved.

The reaction in the carboxamide compound synthesis step is preferably carried out in the presence of an activator composed of a base compound in order to promote the above reaction. Activators composed of basic compounds include alkali metal hydrides, alkaline earth metal hydrides, primary to tertiary alkoxides, alkali metal hydroxides, alkali metal phosphates, organic bases, etc. Any one or two or more selected from the above can be used. As the activator, an acidic catalyst such as trifluoromethanesulfonic acid (TfOH) may be used.

Specifically, as an activator, lithium hydride, sodium hydride, potassium hydride, lithium methoxide, sodium methoxide, potassium methoxide, calcium methoxide, lithium tert-butoxide, sodium tert-butoxide, potassium tert. -Butoxide, triethylamine, diazabicycloundecene, sodium hydroxide, potassium phosphate, sodium phosphate, lithium phosphate and the like can be used. Among these, since the compound represented by the formula (6) can be obtained in a high yield, any one selected from lithium methoxide, sodium methoxide, sodium tert-butoxide, and potassium phosphate can be used as the activator. It is preferable to use it. In particular, it is preferable to use sodium tert-butoxide because the compound represented by the formula (6) can be obtained in a high yield and is easily available.

The amount of the activator used in the carboxamide compound synthesis step is determined by the type of the carbamic acid ester represented by the formula (3) and / or the cyclized product of the carbamic acid ester represented by the formula (4) and the formula (5). It can be appropriately changed depending on the type of blocking agent containing the pyrazole ring shown. For example, when the blocking agent containing the pyrazole ring represented by the formula (5) is 3,5-dimethylpyrazole, the activator may be used in the range of 1 equivalent to 5 equivalents with respect to 1 equivalent of the blocking agent. Preferably, it is more preferably used in the range of 1 equivalent to 2 equivalents. When the amount of the activator used is 1 equivalent or more with respect to 1 equivalent of the blocking agent, the reaction promoting effect by using the activator becomes remarkable. Further, when the amount of the activator used is 5 equivalents or less with respect to 1 equivalent of the blocking agent, the amount of the activator used is large, and therefore, depending on the solvent type used (for example, N, N-dimethylformamide (DMF)). Can prevent the solvent from being easily decomposed.

In the production method of the present embodiment, the carbamic acid ester synthesis step is preferably a step of reacting the dimethyl carbonate represented by the following formula (11) with the ethanolamine represented by the following formula (12). As a result, the carbamic acid ester represented by the following formula (13) may be synthesized, or the cyclized product of the carbamic acid ester represented by the following formula (14) may be synthesized. Further, the carboxamide compound synthesis step can be carried out even when both the compounds represented by the formulas (13) and (14) are mixed. Therefore, in the carbamic acid ester synthesis step, if it is not necessary to synthesize only one of them, both the compounds represented by the formulas (13) and the formula (14) may be synthesized at the same time.

When the carbamic acid ester represented by the formula (13) is synthesized in preference to the cyclized product of the carbamic acid ester represented by the formula (14), for example, the dialkyl carbonate represented by the formula (11) is used in the formula (11). It is supplied in excess of 1.1 times equivalent to the ethanolamine shown in 12), and reacted at 50 to 150 ° C. for 1 to 10 hours in a closed system so that alkanol (methanol) does not come out of the system. Then, the heat source may be removed and excess dialkyl carbonate may be removed under a reduced pressure atmosphere. Excess carbonate may be removed under a reduced pressure atmosphere between the reaction temperature and cooling to room temperature (for example, until cooled to 100 ° C.), or after cooling to around room temperature, a reduced pressure atmosphere. Excess carbonate may be removed below.
Further, when the cyclized product of the carbamic acid ester represented by the formula (14) is synthesized almost selectively, for example, the method shown below is used. First, the dialkyl carbonate represented by the formula (11) is supplied in an amount of 1.0 to 1.3 times the ethanolamine represented by the formula (12), and an activator composed of the above-mentioned basic compound is added. The reaction is carried out at 70 to 150 ° C. for 2 to 20 hours in an open system in which the produced alkanol is easily distilled off. After the ethanolamine represented by the formula (12) is substantially eliminated by the reaction, the remaining dialkyl carbonate represented by the formula (11) is distilled off. At the same time, the carbamic acid ester represented by the formula (13) contained in the reaction system is heated (80 to 150 ° C.) to promote the dealkanol reaction (demethanolation reaction), and the cyclized product represented by the formula (14) is promoted. Convert to.

When both the compounds represented by the formula (13) and the compound represented by the formula (14) are synthesized at the same time, for example, the method shown below may be used. First, the dialkyl carbonate represented by the formula (11) and the ethanolamine represented by the formula (12) are reacted in equimolar amounts. After the ethanolamine represented by the formula (12) is substantially eliminated by the reaction, heating is performed. As a result, a part of the carbamic acid ester represented by the formula (13) contained in the reaction system is subjected to a demethanol reaction to be converted into a cyclized product represented by the formula (14). At this time, for demethanolizing the carbamic acid ester represented by the formula (13) so that the mixing ratio of the compound represented by the formula (13) and the compound represented by the formula (14) is within a predetermined range. Adjust the heating conditions as appropriate. The higher the heating temperature and the longer the heating time, the more easily the compound represented by the formula (13) is converted into the cyclized product represented by the formula (14).

In the carbamic acid ester synthesis step, when a compound having an amino group and a hydroxy group represented by the general formula (2) in which ^{R 2 has 2 carbon atoms is used, the reaction proceeds without using a catalyst.} , The reaction rate can be increased by using a catalyst. When a compound having an amino group and a hydroxy group represented by the general formula (2) in which ^{R 2 has 3 or more carbon atoms is used, a catalyst is used.} When a catalyst is used, the mixing ratio of the compound represented by the formula (3) and the compound represented by the formula (4) can be adjusted according to the type and amount of the catalyst used. For example, when a strong base such as NaOMe or NaOtBu is used as the catalyst, more compounds represented by the formula (4) are more likely to be produced as compared with the compound represented by the formula (3).
As described above, the compound represented by the formula (13) and the compound represented by the formula (14) can be synthesized preferentially.
In the present embodiment, the carbamate ester synthesis step is completed at the stage where the ethanolamine represented by the formula (12) is converted into the compound represented by the formula (13) and / or the compound represented by the formula (14). Then, the process moves to the carboxamide compound synthesis step.

In the production method of the present embodiment, the carboxamid compound synthesis step is the carbamic acid ester represented by the formula (13) produced in the carbamic acid ester synthesis step and 3,5-dimethylpyrazole represented by the following formula (15). The step of reacting with the sodium salt of 3,5-dimethylpyrazole represented by the following formula (25) is preferable. As a result, as represented by the following formula, the compound represented by the following formula (16) is obtained.
Further, in the carboxamide compound synthesis step, 2-oxazolidinone, which is a cyclized product of the carbamic acid ester represented by the formula (14) produced in the carbamic acid ester synthesis step, and 3,5-dimethyl represented by the formula (15). It may be a step of reacting with pyrazole or a sodium salt of 3,5-dimethylpyrazole represented by the following formula (25). Also in this case, as shown by the following formula, the compound represented by the formula (16) is obtained.

The carboxamide compound synthesis step is represented by the formula (14) at the same time as the reaction of the carbamic acid ester represented by the formula (13) with 3,5-dimethylpyrazole (and / or the sodium salt of 3,5-dimethylpyrazole). It may be a step of reacting a cyclized product of a carbamic acid ester with 3,5-dimethylpyrazole (and / or a sodium salt of 3,5-dimethylpyrazole). That is, in the carboxamide compound synthesis step, a mixture of the carbamic acid ester represented by the formula (13) and the cyclized product of the carbamic acid ester represented by the formula (14) may be used as a raw material. Also in this case, the compound represented by the formula (16) can be obtained.

According to the method for producing a compound of the present embodiment, the compound represented by the formula (6) can be produced without using a compound containing a halogen. In the compound represented by the general formula (6), a nitrogen atom of a blocking agent containing a pyrazole ring represented by the general formula (5) is bonded to a carbon atom forming a urethane bond to form a urethane bond. It has a structure in which a hydroxy group is bonded to a nitrogen atom via an alkyl group. Therefore, the compound represented by the general formula (6) can be used as a material for various compounds as shown below.

That is, the compound represented by the general formula (6) is obtained by reacting the hydroxy group in the compound with the functional group of the compound having a functional group such as an isocyanato group, an epoxy group, a carboxy group and an ester group. Reacts with various compounds. Therefore, the compound represented by the general formula (6) is highly versatile and can be used as a material for various compounds having a polyfunctional group.
In addition, the compound represented by the general formula (6) has a blocked isocyanate group and a hydroxy group. Therefore, as shown by the following formula, the compound represented by the general formula (6) can be self-polymerized.

（式（２７）および式（２８）において、Ｒ^２は、式（６）と同じである。）

(In equations (27) and (28), R ² is the same as in equation (6).)

As shown by the above formula, the compound represented by the general formula (6) dissociates the blocking agent represented by the general formula (5) by heating to regenerate the isocyanate group (-NCO). .. The compound represented by the general formula (27) having a regenerated isocyanato group reacts with the hydroxy group having another molecule (the compound represented by the formula (27)) to form a urethane bond (-NH-CO-O-). Form and polymerize. As a result, the polymer represented by the general formula (28) (n in the formula is the number of repetitions) is formed.

The structure of the compound represented by the general formula (6) produced by the production method of the present embodiment includes, for example, nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), infrared spectroscopy (IR), and ultraviolet. -The structure can be confirmed by using known methods such as visible spectroscopy (UV-VIS absorption spectrum) and elemental analysis.

<Compound>
The hydroxyalkylcarboxamide compound of the present embodiment is represented by the following general formula (60).

（式（６０）において、Ｒ^２０は−ＣＨ_２−ＣＨ_２−ＣＨ_２−を示す。Ｒ^３０およびＲ^５０はそれぞれ−Ｈ、−ＣＨ_３または−ＣＨ_２−ＣＨ_３のいずれかを示し、Ｒ^４０は−Ｈを示す。）

(In formula (60), R ²⁰ represents −CH ₂ −CH ₂ −CH ₂ −. R ³⁰ and R ⁵⁰ represent either −H, −CH ₃ or −CH ₂ −CH ₃ , respectively, and R ⁴⁰ indicates -H.)

^{R 30} and R ⁵⁰ in the formula (60) are any of -H, -CH ₃ , and -CH _2- CH ₃ , respectively, and are the same as ^{R 3} and R ⁵ in the formula (6). ^{R 30} and R ⁵⁰ in the formula (60) _{are −CH 3} because the blocking agent is easily dissociated by heating and the isocyanato group is regenerated into a highly versatile product. preferable.
The hydroxyalkylcarboxamide compound of the present embodiment has a block isocyanate group and a hydroxy group, is useful as a material for various compounds having a polyfunctional group, and is highly versatile.

[Other examples]
In the production method of the present embodiment, a carbamic acid ester represented by the formula (3) and / or a cyclized product of the carbamic acid ester represented by the formula (4) was synthesized by carrying out a carbamic acid ester synthesis step. However, the method for synthesizing the carbamic acid ester represented by the formula (3) and / or the cyclized product of the carbamic acid ester represented by the formula (4) is not limited to the above-mentioned method, and any method may be used. May be good.

Hereinafter, the present invention will be described in more detail with reference to Examples. The present invention is not limited to the following examples.
"Examples 1 to 11"
The compound represented by the formula (16) was synthesized by the method shown below.

(Carbamic acid ester synthesis step)
55 g [0.60 mol] of dimethyl carbonate (manufactured by Tokyo Chemical Industry Co., Ltd.) and 31 g [0.50 mol] of ethanolamine (manufactured by Tokyo Chemical Industry Co., Ltd.) are placed in a closed container (eggplant flask with glass stopper (200 mL)). The reaction was carried out at 80 ° C. for 4 hours under solvent-free conditions.
The obtained reaction solution was concentrated under reduced pressure to remove unreacted dimethyl carbonate, and analyzed using gas chromatography (GC2014; manufactured by Shimadzu Corporation). As a result, the product in the reaction solution contained 95% by mass of the carbamic acid ester represented by the formula (13) and 5% by mass of the cyclized product of the carbamic acid ester represented by the formula (14). The obtained product (55.4 g) was not purified and was used as it was as a raw material in the carboxamide compound synthesis step.

(Carboxamide compound synthesis step)
The product (carbamic acid ester) produced in the carbamic acid ester synthesis step in the presence of N, N-dimethylformamide (DMF) (manufactured by Tokyo Chemical Industry Co., Ltd.) as the activator and solvent shown in Table 1 and a block. 3,5-Dimethylpyrazole (manufactured by Tokyo Chemical Industry Co., Ltd.) represented by the formula (15) as an agent was reacted at the reaction temperature and reaction time shown in Table 1. As a result, the hydroxyalkylcarboxamide compound represented by the formula (16) was obtained.
Table 1 shows the types and amounts of carbamic acid esters, blocking agents, activators, and solvents used in the carboxamide compound synthesis step.

As the activator shown in Table 1, those shown below were used.
MeOLi: Lithium methoxyde (manufactured by SIGMA-ALDRICH)
MeONa: Sodium methoxide (manufactured by Tokyo Chemical Industry Co., Ltd.)
MeOK: Potassium methoxyde (manufactured by SIGMA-ALDRICH)
(MeO) ₂ Ca: Calcium methoxyde (manufactured by SIGMA-ALDRICH)
tBuOLi: Lithium tert-butoxide (manufactured by SIGMA-ALDRICH)
tBuONa: Sodium tert-butoxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)
tBuOK: Potassium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.)
Triethylamine: (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)
Diazabicycloundesen: (manufactured by Tokyo Chemical Industry Co., Ltd.)
NaOH: Sodium hydroxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)
K ₃ PO ₄ : Potassium Phosphate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)

The hydroxyalkylcarboxamide compounds obtained by the production methods of Examples 1 to 11 were analyzed by gas chromatography (GC2014; manufactured by Shimadzu Corporation) using biphenyl as an internal standard substance, and yielded by the following formula. The rate was calculated. The results are shown in Table 1.
Yield (%) = (Production amount of target compound (mol) / Amount of carbamic acid ester used (mol)) x 100

The hydroxyalkylcarboxamide compounds obtained by the production methods of Examples 1 to 11 were measured by ¹ H-NMR and ¹³ C-NMR using an NMR (Nuclear Magnetic Resonance) apparatus (Bruker Avance III), respectively. The structure was identified by the following results. FIG. 1 is a ¹ H-NMR measurement chart of Example 1. FIG. 2 is a ¹³ C-NMR measurement chart of Example 1.
As a result, it was confirmed that the hydroxyalkylcarboxamide compounds obtained by the production methods of Examples 1 to 11 were all hydroxyalkylcarboxamide compounds represented by the formula (16).

^{1 1} H-NMR (600MHz, CDCl ₃ , 300K) δ (ppm): 2.21 (S, 3H, Me), 2.22 (S, 3H, Me), 3.70 (q, J = 5.7) _{, 2H, -CH 2 -),} 4.09 (t, J = 5.6,2H, -CH 2 -), 5.81 (S, 1H, CH), 6.54 (S, 1H, OH) , 8.17 (S, 1H, NH)
^{13 C {1 H} -NMR (} 125MHz, CDCl 3, 300K) δ (ppm): 10.9 (S), 13.2 (S), 37.8 (S), 46.9 (S), 105 .5 (S), 140.1 (S), 147.8 (S), 161.4 (S)

As shown in Table 1, in Examples 1 to 11 using the activator shown in Table 1, the hydroxyalkylcarboxamide compound represented by the formula (16) was obtained.
In particular, in Example 1 using lithium methoxide as an activator, Example 2 using sodium methoxide, Example 6 using sodium tert-butoxide, and Example 11 using potassium phosphate, the formula ( The compound represented by 16) was obtained in a high yield of 40% or more.

"Example 12 to 22"
(Carbamic acid ester synthesis step)
The carbamic acid ester synthesis step was carried out in the same manner as in Example 1.

(Carboxamide compound synthesis step)
In the presence of sodium tert-butoxide as an activator, in N, N-dimethylformamide (DMF) as a solvent, the product (carbamic acid ester) produced in the carbamic acid ester synthesis step and as a blocking agent. The 3,5-dimethylpyrazole represented by the formula (15) was reacted at the reaction temperature and reaction time shown in Table 2. As a result, the compound represented by the formula (16) was obtained.
Table 2 shows the types and amounts of carbamic acid esters, blocking agents, activators, and solvents used in the carboxamide compound synthesis step.

The yields of the hydroxyalkylcarboxamide compounds obtained by the production methods of Examples 12 to 22 were calculated in the same manner as in Example 1. The results are shown in Table 2.

In addition, the structures of the hydroxyalkylcarboxamide compounds obtained by the production methods of Examples 12 to 22 were specified in the same manner as in Example 1.
As a result, it was confirmed that the hydroxyalkylcarboxamide compounds obtained by the production methods of Examples 12 to 22 were all hydroxyalkylcarboxamide compounds represented by the formula (16).

As shown in Table 2, in each of Examples 12 to 22, the hydroxyalkylcarboxamide compound represented by the formula (16) was obtained.
In Example 12 in which the amount of the activator used was 1.5 equivalents with respect to 1 equivalent of the blocking agent, Example 14 in which the amount of the activator was 2.0 equivalents, and the amount of the activator used was 1. Higher yields were obtained as compared to Example 13, which is 0 equivalents.

As shown in Table 2, in Example 18 in which the amount of solvent used is 4.0 ml, Example 12 in which the amount of solvent used is 0.5 ml, Example 16 in which the amount of solvent used is 1.0 ml, and the amount of solvent used. Higher yields were obtained as compared to Example 17 in which the volume was 2.0 ml.
As shown in Table 2, in Example 12 having a reaction time of 5 hours, a higher yield was obtained as compared with Example 14 having a reaction time of 4 hours. Further, in Example 17 having a reaction time of 5 hours, a higher yield was obtained as compared with Example 19 having a reaction time of 17 hours.

"Example 23-Example 26"
(Carbamic acid ester synthesis step)
The carbamic acid ester synthesis step was carried out in the same manner as in Example 1.

(Carboxamide compound synthesis step)
In the presence of sodium tert-butoxide as an activator, the product (carbamic acid ester) produced in the carbamic acid ester synthesis step in the solvent shown in Table 3 is represented by the formula (15) as a blocking agent. 3,5-Dimethylpyrazole was reacted at the reaction temperature and reaction time shown in Table 3. As a result, the compound represented by the formula (16) was obtained.
Table 3 shows the types and amounts of carbamic acid esters, blocking agents, activators, and solvents used in the carboxamide compound synthesis step.

As the solvent shown in Table 3, the solvent shown below was used.
DMF: N, N-dimethylformamide (manufactured by Tokyo Chemical Industry Co., Ltd.)
DMAc: N, N-dimethylacetamide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)
NMP: N-methyl-2-pyrrolidone (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)
Acetonitrile: (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)
DMSO: Dimethyl sulfoxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)

The yields of the hydroxyalkylcarboxamide compounds obtained by the production methods of Examples 23 to 26 were calculated in the same manner as in Example 1. The results are shown in Table 3. For comparison, Table 3 also shows the results of Example 13 shown in Table 2.

In addition, the structures of the hydroxyalkylcarboxamide compounds obtained by the production methods of Examples 23 to 26 were specified in the same manner as in Example 1.
As a result, it was confirmed that the hydroxyalkylcarboxamide compounds obtained by the production methods of Examples 23 to 26 were all hydroxyalkylcarboxamide compounds represented by the formula (16).

As shown in Table 3, in each of Examples 23 to 26, the hydroxyalkylcarboxamide compound represented by the formula (16) was obtained.
In particular, in Example 13 using N, N-dimethylformamide (DMF) as the solvent, the compound represented by the formula (16) was obtained in a high yield.

"Example 27"
(Carbamic acid ester synthesis step)
The carbamic acid ester synthesis step was carried out in the same manner as in Example 1.

(Carboxamide compound synthesis step)
The product (carbamic acid ester) produced in the carbamic acid ester synthesis step and the 3,5-dimethyl represented by the formula (25) as a blocking agent in the solvent shown in Table 4 without using an activator. The sodium salt of pyrazole was reacted at the reaction temperature and reaction time shown in Table 4. As a result, the compound represented by the formula (16) was obtained.

As the sodium salt of 3,5-dimethylpyrazole as a blocking agent, one synthesized by the following method was used.
Dissolve 1.9 g (20 mmol) of 3,5-dimethylpyrazole (manufactured by Tokyo Chemical Industry Co., Ltd.) in 2 mL of tetrahydrofuran (THF), add 1.1 g (20 mmol) of sodium methoxide (manufactured by Tokyo Chemical Industry Co., Ltd.), and add 1 hour. Refluxed. Then, by concentrating under reduced pressure, 2.3 g of sodium salt of 3,5-dimethylpyrazole was obtained as white crystals.

Table 4 shows the types and amounts of carbamic acid esters, blocking agents, and solvents used in the carboxamide compound synthesis step.

The yield of the hydroxyalkylcarboxamide compound obtained by the production method of Example 27 was calculated in the same manner as in Example 1. The results are shown in Table 4.
Further, the structure of the hydroxyalkylcarboxamide compound obtained by the production method of Example 27 was specified in the same manner as in Example 1.
As a result, it was confirmed that the hydroxyalkylcarboxamide compound obtained by the production method of Example 27 was the hydroxyalkylcarboxamide compound represented by the formula (16).

As shown in Table 4, in Example 27 using the sodium salt of 3,5-dimethylpyrazole represented by the formula (25) as the blocking agent, it is represented by the formula (16) without using an activator. The hydroxyalkylcarboxamide compound was obtained in a high yield of 50% or more.

"Example 28"
A hydroxyalkylcarboxamide compound was prepared in the same manner as in Example 21 except that pyrazole (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 3,5-dimethylpyrazole represented by the formula (15) as a blocking agent. Manufactured.
Table 4 shows the types and amounts of carbamic acid esters, blocking agents, activators, solvents used in the carboxamide compound synthesis step, reaction temperature, and reaction time.
The yield of the hydroxyalkylcarboxamide compound obtained by the production method of Example 28 was calculated in the same manner as in Example 1. The results are shown in Table 4.

^{The hydroxyalkylcarboxamide compound obtained by the production method of Example 28 was measured by 1} H-NMR and ¹³ C-NMR using an NMR (Nuclear Magnetic Resonance) apparatus (Bruker Availability III), and the structure was obtained according to the following results. Was identified. FIG. 3 is a ¹ H-NMR measurement chart of Example 28. FIG. 4 is a ¹³ C-NMR measurement chart of Example 28.
As a result, it was confirmed that the hydroxyalkylcarboxamide compound obtained by the production method of Example 28 was the hydroxyalkylcarboxamide compound represented by the formula (16).

^{1 1} H-NMR (600MHz, CDCl ₃ , 300K) δ (ppm): 3.78 (dd, J = 11, 5.7Hz, 2H, -CH _2- ), 4.32 (t, J = 5.7Hz) , 2H, -CH _2- ), 6.30 (t, J = 2.1Hz, 1H, CH), 7.42 (d, J = 2.1Hz, 1H, CH), 7.57 (d, J) = 2.1Hz, 1H, CH), 8.18 (S, 1H, NH)
^{13 C {1 H} -NMR (} 125MHz, CDCl 3, 300K) δ (ppm): 38.3 (S), 50.7 (S), 106.0 (S), 130.5 (S), 139 .4 (S), 161.3 (S)

As shown in Table 4, in Example 28 using pyrazole as a blocking agent, the hydroxyalkylcarboxamide compound represented by the formula (16) was obtained in a high yield of 60% or more.

"Example 29"
Hydroxyalkylcarboxamide compounds in the same manner as in Example 21 except that 3-amino-1-propanol (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of ethanolamine as the compound having an amino group and a hydroxy group. Manufactured.
Table 4 shows the types and amounts of carbamic acid esters, blocking agents, activators, solvents used in the carboxamide compound synthesis step, reaction temperature, and reaction time.
The yield of the hydroxyalkylcarboxamide compound obtained by the production method of Example 29 was calculated in the same manner as in Example 1. The results are shown in Table 4.

^{The hydroxyalkylcarboxamide compound obtained by the production method of Example 29 was measured by 1} H-NMR and ¹³ C-NMR using an NMR (Nuclear Magnetic Resonance) apparatus (Bruker Availability III), and the structure was obtained according to the following results. Was identified. FIG. 5 is a ¹ H-NMR measurement chart of Example 29. FIG. 6 is a ¹³ C-NMR measurement chart of Example 29.
As a result, hydroxyalkyl carboxamide compound obtained by the method of Example 29, hydroxyalkyl carboxamide compound represented by the formula (60) in (equation ^{(60), R 20} is _-CH 2 _-CH 2 -CH ₂ - R ³⁰ and R ⁵⁰ each _{indicate -CH 3} , and R ⁴⁰ indicates -H).

^{1 1} H-NMR (600 MHz, CD ₃ OD, 300 K) δ (ppm): 1.96 (quint, J = 7.1 Hz, 2H, -CH _2- ), 2.16 (s, 3H, CH ₃ ), 2.24 (s, 3H, CH ₃ ), 3.20 (t, J = 7.1Hz, 2H, -CH _2- ), 5.83 (s, 1H, CH), 8.05 (s, 1H) , NH)
¹³ C { ¹ H} -NMR (125 MHz, CD ₃ OD, 300 K) δ (ppm): 10.8 (S), 13.2 (S), 30.9 (S), 36.3 (S), 46.7 (S), 106.1 (S), 141.1 (S), 148.7 (S), 163.9 (S)

As shown in Table 4, in Example 29 using 3-amino-1-propanol as the compound having an amino group and a hydroxy group, the hydroxyalkylcarboxamide compound represented by the formula (60) had a high yield of 39%. Obtained at a rate.

"Example 30"
A hydroxyalkylcarboxamide compound was produced in the same manner as in Example 13 except that the reaction was carried out at the reaction temperatures shown in Table 5.
Table 5 shows the types and amounts of carbamic acid esters, blocking agents, activators, solvents used in the carboxamide compound synthesis step, reaction temperature, and reaction time.
The yield of the hydroxyalkylcarboxamide compound obtained by the production method of Example 30 was calculated in the same manner as in Example 1. The results are shown in Table 5. For comparison, Table 5 also shows the results of Example 13 shown in Table 2.

The structure of the hydroxyalkylcarboxamide compound obtained by the production method of Example 30 was specified in the same manner as in Example 1.
As a result, it was confirmed that the hydroxyalkylcarboxamide compound obtained by the production method of Example 30 was the hydroxyalkylcarboxamide compound represented by the formula (16).

As shown in Table 5, in Example 13 having a reaction temperature of 150 ° C., the yield of the hydroxyalkylcarboxamide compound represented by the formula (16) was higher than that in Example 30 having a reaction temperature of 130 ° C. Obtained in.

"Example 31"
A hydroxyalkylcarboxamide compound was produced in the same manner as in Example 12 except that the reaction was carried out at the reaction temperatures shown in Table 5.
Table 5 shows the types and amounts of carbamic acid esters, blocking agents, activators, solvents used in the carboxamide compound synthesis step, reaction temperature, and reaction time.
The yield of the hydroxyalkylcarboxamide compound obtained by the production method of Example 31 was calculated in the same manner as in Example 1. The results are shown in Table 5. For comparison, Table 5 also shows the results of Example 12 shown in Table 2.

The structure of the hydroxyalkylcarboxamide compound obtained by the production method of Example 31 was specified in the same manner as in Example 1.
As a result, it was confirmed that the hydroxyalkylcarboxamide compound obtained by the production method of Example 31 was the hydroxyalkylcarboxamide compound represented by the formula (16).

As shown in Table 5, in Example 12 having a reaction temperature of 150 ° C., the yield of the hydroxyalkylcarboxamide compound represented by the formula (16) was higher than that in Example 31 having a reaction temperature of 100 ° C. Obtained in.

"Example 32"
A hydroxyalkylcarboxamide compound was produced in the same manner as in Example 12 except that trifluoromethanesulfonic acid (TfOH) (manufactured by Tokyo Chemical Industry Co., Ltd.) was used as the activator.
Table 5 shows the types and amounts of carbamic acid esters, blocking agents, activators, solvents used in the carboxamide compound synthesis step, reaction temperature, and reaction time.
The yield of the hydroxyalkylcarboxamide compound obtained by the production method of Example 32 was calculated in the same manner as in Example 1. The results are shown in Table 5.

The structure of the hydroxyalkylcarboxamide compound obtained by the production method of Example 32 was specified in the same manner as in Example 1.
As a result, it was confirmed that the hydroxyalkylcarboxamide compound obtained by the production method of Example 32 was the hydroxyalkylcarboxamide compound represented by the formula (16).

The present invention can be used as a material for various compounds having a polyfunctional group and a method for producing the same.

Claims (9)

In the presence of a solvent, one or both of the carbamic acid ester represented by the following general formula (3) and the cyclized compound of the carbamic acid ester represented by the following general formula (4), and the following general formula (5) A method for producing a hydroxyalkyl carboxamide compound, which comprises a first step of synthesizing a compound represented by the following general formula (6) by reacting with a blocking agent containing a pyrazole ring shown.

(In the formula (3), R ¹ represents -CH ₃ and -CH _2- CH _{3. In the} formulas (3), (4) and (6), R ² is a direct number of carbon atoms 2 to 6. Indicates a chain alkylene group or a cycloalkylene group having 4 to 6 carbon atoms. In formulas (5) and (6), R ³ and R ⁵ are of −H, −CH ₃ or −CH ₂ −CH ₃ , respectively. Either is indicated, and R ⁴ indicates −H. In the formula (5), X indicates either a hydrogen atom or an alkali metal atom.) Before the first step,
By reacting the dialkyl carbonate represented by the following general formula (1) with the compound having an amino group and a hydroxy group represented by the following general formula (2), the carbamic acid ester represented by the following general formula (3) can be obtained. The method for producing a hydroxyalkyl carboxamide compound according to claim 1, wherein the second step of synthesizing one or both of the cyclized compounds of the carbamic acid ester represented by the following general formula (4) is carried out.

(In the formula (1) and (3), ^{R 1} is _{-CH 3,} 2 one of ^{R 1} are shown a -CH 2 -CH _3. Equation (1) is the same. Equation (2) to ( In 4), R2 represents a linear alkylene group having 2 to 6 carbon atoms or a cycloalkylene group having 4 to 6 carbon atoms.) In formula (3), R ¹ represents −CH ₃ , and in formulas (3), (4) and (6), R ² represents −CH ₂ −CH ₂ −, and formulas (5) and formula (5) and formula (6). (6) The method for producing a hydroxyalkylcarboxamide compound according to claim 1 or 2 ^{, wherein R 3} and R ⁵ show −CH ₃ and R ^{4 shows −H.} The first step is characterized in that one or both of the carbamic acid ester and the cyclized product is reacted with the blocking agent in the presence of an activator composed of a basic compound. The method for producing a hydroxyalkylcarboxamide compound according to any one of 1 to 3. The activator is any one selected from alkali metal hydrides, alkaline earth metal hydrides, primary to tertiary alkoxides, alkali metal hydroxides, and alkali metal phosphates. The method for producing a hydroxyalkylcarboxamide compound according to claim 4, wherein the number is two or more. The method for producing a hydroxyalkylcarboxamide compound according to claim 4, wherein the activator is any one selected from lithium methoxide, sodium methoxide, and sodium tert-butoxide. Claims 1 to 6, wherein in the first step, one or both of the carbamic acid ester and the cyclized compound are reacted with the blocking agent in an amide-based solvent. The method for producing a hydroxyalkylcarboxamide compound according to any one of the above. The method for producing a hydroxyalkylcarboxamide compound according to claim 7, wherein the amide-based solvent is N, N-dimethylformamide. A hydroxyalkylcarboxamide compound represented by the following general formula (60).

(In formula (60), R ²⁰ represents −CH ₂ −CH ₂ −CH ₂ −. R ³⁰ and R ⁵⁰ represent either −H, −CH ₃ or −CH ₂ −CH ₃ , respectively, and R ⁴⁰ indicates -H.)

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