KR102599566B1 - Process for preparing acrylamides compounds and its derivatives - Google Patents

Abstract

The present invention relates to a method for producing an acrylamide compound and its derivatives, wherein an acrylamide compound and its derivatives can be prepared in a one-step reaction from an azido compound under mild reaction conditions.

Description

Method for producing acrylamide compounds and derivatives thereof {PROCESS FOR PREPARING ACRYLAMIDES COMPOUNDS AND ITS DERIVATIVES}

The present invention relates to a method for producing an acrylamide compound and its derivatives, and more specifically, to a method for producing an acrylamide compound and its derivatives that can synthesize acrylamide in a one-step process from an azido compound.

Acrylamide and its derivatives play an important role in various organic reactions such as nucleophilic addition, cycloaddition, and radical reaction, so they are used as intermediates or ligands for numerous biologically active substances and as precursors for polymer synthesis.

In addition, acrylamide derivatives are widely used as precursors for polyacrylamide-based polymer compounds, and polyacrylamide is widely used in dyes, contact lenses, cosmetics, and chemical grouting agents. In the defense field, it is also used as a soil stabilizer during helicopter landings, and due to its electrical conductivity, it is also attracting attention as an electrolyte for future combat uniforms with electronic performance. Additionally, research on poly(N-alkylacrylamide)s and poly(N-alkylmethacrylamide)s, which have temperature-responsive microgel properties, is being actively conducted recently. Accordingly, research on synthesizing acrylamide single molecules with various substituents is attracting attention.

Meanwhile, in pharmacochemistry, acrylamide acts as a Michael receptor and is used as an important framework in designing various drugs. Since 1990, methods for inactivating target biomolecules by forming covalent bonds with selective small molecules have received attention, and this field has recently developed rapidly. As representative examples, ibrutinib, osimertinib, antiallergenic tranilast, and anticonvulsant ilepcimide entered the market, and accordingly, acrylamide became a major framework for designing target covalent inhibitors (TCIs). Ibrutinib and osimertinib are known to form covalent bonds with target cells through a conjugate addition reaction with amino acids containing heteroatoms in the activated site. Because of this sensitivity to conjugate addition, acrylamide is often introduced at the final stage of synthesis.

Acrylamide compounds, which can be applied to various fields, are mainly synthesized by the following method. The first method is to use the Ritter reaction. As shown in the reaction formula below, sulfuric acid is added dropwise to acrylonitrile and alcohol to react. (J. Org. React. 1969, 17, 213)

This method has a limitation in the scope of the reaction because it uses a strong acid, and has the disadvantage of increasing the risk of the process and lowering the yield due to the large amount of heat generated during the scale-up reaction.

Second, as shown in the reaction formula below, acrylamide is obtained by reacting amine and acryloyl chloride in the presence of a base.

Because of its sensitivity to conjugate addition, acrylamide is often introduced in the final stage of synthesis. When an amine compound is used as an intermediate, it reacts with other compounds during step-by-step reactions due to the reactivity of the amine, generating many by-products. In addition, acrylamide remaining unreacted has the problem of complicated post-reaction treatment and low yield as by-products are generated when acryloyl chloride and base react.

In order to solve the problem of using a highly reactive amine compound as a starting material, the third method is to obtain acrylamide through a two-step reaction from an azido compound that is easy to introduce. As shown in the reaction formula below, this is a method of reducing the azido group to an amine and then using a base and acryloyl chloride to obtain acrylamide.

Since this method uses an easily introduced azido compound as a starting material, it has the advantage of avoiding using an amine compound as a starting material, which is highly reactive and can generate a lot of by-products during step-by-step reactions. (Eur. J. Org. Chem. 2013, 465-473., Bioorg. Med. Chem. 7, 1999, 1549-1558., Synlett, 2007, 11, 1742-1744., J. Org. Med. Chem. , 2012, 55, 2646., Org. Biomol. Chem. 2003, 1, 2276)

However, the conventional method of synthesizing acrylamide from an azido compound has the limitation of requiring a two-step reaction. There are two methods to reduce the azido group to an amine group in the first step: using H ₂ /Pd or LiAlH ₄ or Staudinger reaction using PPh _3. H ₂ /Pd or LiAlH ₄ , which are strong reducing agents. When used, the yield is lowered because other functional groups are reduced. When reducing using the Staudinger reaction. There is a problem in that it is difficult to remove an equivalent amount of phosphine oxide generated after the reaction. In the second step, this method also uses a base and is difficult to use in mass synthesis due to the high cost of acryloyl chloride.

Therefore, there is a need to develop a new production method that can produce various acrylamide derivatives from azido compounds under easier and milder conditions.

Korean Patent Publication No. 10-0408201 (announced on December 1, 2003) Korean Patent Publication No. 10-1647165 (announced on June 16, 2011)

The purpose of the present invention is to provide a method for producing an acrylamide compound that can easily obtain an acrylamide compound and its derivatives under mild reaction conditions without using an acid or base.

Another object of the present invention is to provide a method for producing an acrylamide compound that can obtain an acrylamide compound and its derivatives with high purity and high yield while reacting under mild conditions.

Another object of the present invention is to provide a method for producing an acrylamide compound by which an acrylamide compound and a derivative thereof can be obtained from an azido compound in a one-pot process.

Another object of the present invention is to provide monomers of acrylamide compounds and their derivatives.

The problem to be solved by the present invention is not limited to the problem(s) mentioned above, and other problem(s) not mentioned will be clearly understood by those skilled in the art from the following description.

In order to solve the above problem, according to one aspect of the present invention, the present invention provides a method for producing an acrylamide compound, comprising reacting an azido compound, a propargyl compound, a solvent, and a catalyst.

Additionally, the present invention relates to an azido compound; Propargyl compounds; menstruum; and reacting a catalyst, wherein the azido compound is represented by the following formula (1):

[Formula 1]

In the above formula, R is a replaceable hydrocarbon group, and represents an alkyl group with 1 to 10 carbon atoms, an aryl group or heteroaryl group with 3 to 10 ring atoms, and the alkyl group, aryl group, and heteroaryl group are halogen, cyano, and hydroxy. , thiol, amino, alkyl, alkyloxy, alkylamino, dialkylamino, aryl, aryloxy, arylamino, diarylamino, or heteroaryl group.

Additionally, the present invention relates to an azido compound; Propargyl compounds; menstruum; and reacting a catalyst, wherein the propargyl compound is represented by the following formula (2):

[Formula 2]

In the above formula, X may be selected from bromine (Br), iodine (I), chlorine (Cl), or tosylate.

The propargyl compound may be contained in a ratio of 0.2 to 5 moles relative to the azido compound.

Additionally, the present invention relates to an azido compound; Propargyl compounds; menstruum; and reacting a catalyst, wherein the solvent includes water (H ₂ O).

The solvent may be water (H ₂ O).

The solvent is dichloromethane (CH ₂ Cl ₂ ), chloroform (CHCl ₃ ), dichloroethane (C ₂ H ₄ Cl ₂ ), acetone (C ₃ H ₆ O ₂ ), ethanol (C ₂ H ₅ OH), and propanol ( C ₃ H ₈ OH) may further be included.

Additionally, the present invention relates to an azido compound; Propargyl compounds; menstruum; And comprising reacting a catalyst, wherein the catalyst is any one of copper sulfate dihydride (CuSO ₄ 5H ₂ O), copper iodide (CuI), copper bromide (CuBr), and copper chloride (CuCl) of an acrylamide compound. Manufacturing method is provided.

The catalyst may further include sodium ascorbate.

Additionally, the present invention relates to an azido compound; Propargyl compounds; menstruum; and reacting a catalyst, wherein the reaction is performed in a one-pot process.

The reaction can be performed at 30 to 80 °C for 2 to 24 hours.

Additionally, the present invention relates to an azido compound; Propargyl compounds; menstruum; It provides a method for producing an acrylamide compound represented by the following formula (3), comprising reacting a catalyst:

[Formula 3]

In the above formula, R is a replaceable hydrocarbon group, and represents an alkyl group with 1 to 10 carbon atoms, an aryl group or heteroaryl group with 3 to 10 ring atoms, and the alkyl group, aryl group, and heteroaryl group are halogen, cyano, and hydroxy. , thiol, amino, alkyl, alkyloxy, alkylamino, dialkylamino, aryl, aryloxy, arylamino, diarylamino, or heteroaryl group.

The acrylamide compound may be a monomer.

According to the method for producing an acrylamide compound and its derivatives of the present invention, an azido compound that is easy to introduce is used as a starting material and easily available materials are used under mild and controllable reaction conditions without using acids or bases. Thus, there is an effect of producing high purity and high yield acrylamide in a one-step reaction.

The effects of the present invention are not limited to the effects described above, and should be understood to include all effects that can be inferred from the configuration of the invention described in the detailed description or claims of the present invention.

Figure 1 is a ¹ H-NMR spectrum of N-benzylacrylamide prepared according to an embodiment of the present invention.
Figure 2 is a ¹ H-NMR spectrum (Figure 2a) and ^{a 13} C-NMR spectrum (Figure 2b) of N-octylacrylamide prepared according to an embodiment of the present invention.
Figure 3 is ^{a 1} H-NMR spectrum (Figure 3a) and ^{a 13} C-NMR spectrum (Figure 3b) of methyl-4-(acrylamidomethyl)benzoate prepared according to an embodiment of the present invention.
Figure 4 shows the ¹ H-NMR spectrum (Figure 4a) and ¹³ C-NMR spectrum (Figure 4b) of N-(4-methylbenzyl)acrylamide prepared according to an embodiment of the present invention.
Figure 5 is ^{a 1} H-NMR spectrum (Figure 5a) and ^{a 13} C-NMR spectrum (Figure 5b) of N-(4-nitrobenzyl)acrylamide prepared according to an embodiment of the present invention.
Figure 6 shows the ¹ H-NMR spectrum (FIG. 6a) and ¹³ C-NMR spectrum (FIG. 6b) of N-(4-(trifluoromethyl)benzyl)acrylamide prepared according to an embodiment of the present invention.

Hereinafter, preferred embodiments according to the present invention will be described in detail with reference to the attached drawings.

The advantages and features of the present invention and how to achieve it will become clear by referring to the embodiments described in detail below along with the accompanying drawings.

However, the present invention is not limited to the embodiments disclosed below and will be implemented in various different forms, but the present embodiments only serve to ensure that the disclosure of the present invention is complete and are within the scope of common knowledge in the technical field to which the present invention pertains. It is provided to fully inform those who have the scope of the invention, and the present invention is only defined by the scope of the claims.

Additionally, in describing the present invention, if it is determined that related known techniques may obscure the gist of the present invention, detailed description thereof will be omitted.

Hereinafter, the present invention will be described in detail.

The present invention provides a method for producing an acrylamide compound represented by Scheme 1 below:

[Scheme 1]

As shown in Scheme 1 above, an acrylamide compound can be prepared by mixing an azido compound, a propargyl compound, and a catalyst in a solvent and reacting. The preparation method of Scheme 1 is for preparing monomers of acrylamide compounds and their derivatives.

The azido compound, which is the starting material for this reaction, is represented by the following formula (1):

[Formula 1]

In the above formula, R is a replaceable hydrocarbon group, and represents an alkyl group with 1 to 10 carbon atoms, an aryl group or heteroaryl group with 3 to 10 ring atoms, and the alkyl group, aryl group, and heteroaryl group are halogen, cyano, and hydroxy. , thiol, amino, alkyl, alkyloxy, alkylamino, dialkylamino, aryl, aryloxy, arylamino, diarylamino, or heteroaryl group.

The propargyl compound is represented by the following formula (2):

[Formula 2]

In the above formula, X may be selected from bromine (Br), iodine (I), chlorine (Cl), or tosylate.

The propargyl compound is preferably contained in a ratio of 0.2 to 5 moles, and more preferably in a ratio of 1 to 5 moles, relative to the azido compound. If the molar ratio of the propargyl compound to the azido compound is outside the range of 0.2 to 5, there may be a problem in which the reaction does not proceed well.

The solvent may include water (H ₂ O), and only water may be used as the solvent.

In addition, the solvent may be dichloromethane (CH ₂ Cl ₂ ), chloroform (CHCl ₃ ), dichloroethane (C ₂ H ₄ Cl ₂ ), acetone (C ₃ H ₆ O ₂ ), ethanol (C ₂ H ₅ OH), It may further include any one of propanol (C ₃ H ₈ OH), of which dichloromethane is preferably used.

As the catalyst, any one of copper sulfate salt (CuSO _4· 5H ₂ O), copper iodide (CuI), copper bromide (CuBr), and copper chloride (CuCl) can be used.

Additionally, the catalyst may further include sodium ascorbate.

The reaction is a one-pot process. That is, it can be performed as a one-step reaction.

Additionally, the reaction is preferably performed at 30 to 80° C. for 2 to 24 hours. If the reaction conditions are outside the above reaction conditions, there is a problem that the reaction does not proceed and a lot of starting materials remain, or the reaction progresses further and acrylamide becomes a polymer.

Through the reaction of Scheme 1, an acrylamide compound represented by the following Chemical Formula 3 can be obtained. The acrylamide compound represented by the following formula (3) includes derivatives of the acrylamide compound.

[Formula 3]

In the above formula, R is a replaceable hydrocarbon group, and represents an alkyl group with 1 to 10 carbon atoms, an aryl group or heteroaryl group with 3 to 10 ring atoms, and the alkyl group, aryl group, and heteroaryl group are halogen, cyano, and hydroxy. , thiol, amino, alkyl, alkyloxy, alkylamino, dialkylamino, aryl, aryloxy, arylamino, diarylamino, or heteroaryl group.

The acrylamide compound may be a monomer.

Hereinafter, preferred examples are presented to aid understanding of the present invention. However, the following examples are merely illustrative of the present invention and the scope of the present invention is not limited to the following examples.

Example

Hereinafter, preferred examples are presented to aid understanding of the present invention. However, the following examples are merely illustrative of the present invention and the scope of the present invention is not limited to the following examples.

In the following examples, various azido compounds, propargyl bromide, CuSO _4· 5H ₂ O, and sodium ascorbate were mixed with water and dichloromethane as solvents and placed in a 50°C bath for 5 hours. Acrylamide derivatives were synthesized by stirring. After cooling to room temperature, it was extracted with dichloromethane, concentrated under reduced pressure, and purified to obtain an acrylamide derivative. This will be described in detail below.

Example 1

Benzyl azide 133 mg (1.00 mmol), propargyl bromide 156 μL (2.00 mmol), CuSO ₄ 5H ₂ O 280 mg (1.1 mmol), sodium ascorbate 30 mg (0.15 mmol) was mixed, 1 mL of water and 0.5 mL of CH ₂ Cl ₂ were added, and the mixture was stirred at 50° C. for 5 hours. After completion of the reaction, the extract was extracted three times with 1.5 mL of CH ₂ Cl ₂ and then columnarized to obtain 90 mg of N-benzylacrylamide with a yield of 56%.

NMR analysis confirmed that N-benzylacrylamide was synthesized (Figure 1).

NMR analysis results:

^1H NMR (500 MHz, Chloroform-d) δ 7.40 - 7.26 (m, 5H), 6.34 (dd, J = 16.9, 1.4 Hz, 1H), 6.11 (dd, J = 17.0, 10.3 Hz, 1H), 5.80 (br, 1H), 5.68 (dd, J = 10.3, 1.4 Hz, 1H), 4.54 (d, J = 5.8 Hz, 2H).

¹³ C NMR (126 MHz, CDCl ₃ ) δ 165.8, 138.1, 130.8, 128.6, 127.7, 127.3, 126.5, 43.5.

Example 2

N-Octylazide 155 mg (1.00 mmol), propargyl bromide 156 μL (2.00 mmol), CuSO ₄ 5H ₂ O 280 mg (1.1 mmol), sodium ascorbate 30 mg (0.15 mmol) of ascorbate) was mixed, 1 mL of water and 0.5 mL of CH ₂ Cl ₂ were added, and the mixture was stirred at 50° C. for 5 hours. After completion of the reaction, the extract was extracted three times with 1.5 mL of CH ₂ Cl ₂ and columnarized to obtain 100 mg of N-octylacrylamide in 50% yield.

NMR analysis confirmed that N-octylacrylamide was synthesized (Figures 2a and 2b).

NMR analysis results:

^1H NMR (500 MHz, Chloroform- d ) δ 6.25 (s, 1H), 6.22 (d, J = 17.3 Hz, 1H), 6.11 (dd, J = 17.0, 10.2 Hz, 1H), 5.56 (d, J) = 10.2 Hz, 1H), 3.27 (q, J = 6.8 Hz, 2H), 1.49 (t, J = 7.2 Hz, 2H), 1.26 (ddd, J = 18.4, 12.9, 6.5 Hz, 12H), 0.84 (t , J = 6.8 Hz, 3H).

¹³ C NMR (126 MHz, CDCl ₃ ) δ 165.77, 131.21, 125.92, 39.73, 31.85, 29.61, 29.34, 29.26, 27.04, 22.69, 14.12.

Example 3

191 mg (1.00 mmol) of methyl-4-(azidomethyl)benzoate and 156 μL (2.00 mmol) of propargyl bromide, 280 mg of CuSO ₄ 5H ₂ O (1.1 mmol) and 30 mg (0.15 mmol) of sodium ascorbate were mixed, 1 mL of water and 0.5 mL of CH ₂ Cl ₂ were added, and the mixture was stirred at 50° C. for 5 hours. After completion of the reaction, the extract was extracted three times with 1.5 mL of CH ₂ Cl ₂ and columnarized to obtain 160 mg of methyl-4-(acrylamidomethyl)benzoate with a yield of 71%.

Through NMR analysis, it was confirmed that methyl-4-(acrylamidomethyl)benzoate was synthesized (FIGS. 3a and 3b).

NMR analysis results:

¹ H NMR (500 MHz, Chloroform-d) δ 7.99 (ddd, J = 6.5, 4.3, 2.1 Hz, 2H), 7.39 - 7.33 (m, 2H), 6.35 (d, J = 17.0 Hz, 1H), 6.19 - 6.09 (m, 1H), 5.95 (s, 1H), 5.70 (d, J = 10.3 Hz, 1H), 4.61 - 4.55 (m, 2H), 3.94 - 3.88 (m, 3H).

¹³ C NMR (126 MHz, CDCl ₃ ) δ 166.91, 165.59, 143.41, 130.55, 130.19, 129.62, 127.78, 127.39, 77.41, 77.16, 76.91, 52.29, 43.45.

Example 4

1-(azidomethyl)-4-methylbenzene (1-(azidomethyl)-4-methylbenzene) 147 mg (1.00 mmol) and propargyl bromide 156 μL (2.00 mmol), CuSO ₄ 5H ₂ Mix 280 mg (1.1 mmol) of O and 30 mg (0.15 mmol) of sodium ascorbate, add 1 mL of water and 0.5 mL of CH ₂ Cl ₂ , and stir the mixture at 50°C for 5 hours. did. After completion of the reaction, the extract was extracted three times with 1.5 mL of CH ₂ Cl ₂ and columnarized to obtain 130 mg of N-(4-(methylbenzyl)acrylamide) with a yield of 74%.

Through NMR analysis, it was confirmed that N-(4-methylbenzyl)acrylamide was synthesized (Figures 4a and 4b).

NMR analysis results:

^1H NMR (500 MHz, Chloroform- d ) δ 7.07 - 6.99 (m, 3H), 6.40 (s, 1H), 6.17 (d, J = 17.0 Hz, 1H), 6.09 - 5.99 (m, 1H), 5.51 (d, J = 10.2 Hz, 1H), 4.31 (d, J = 5.8 Hz, 2H), 2.23 (s, 2H).

¹³ C NMR (126 MHz, CDCl3) δ 165.58, 137.17, 135.13, 130.88, 129.36, 127.88, 126.48, 43.39, 21.13.

Example 5

에서 5 시간 동안 교반하였다. 반응 종료 후 CH₂Cl₂ 1.5 mL로 세 번 추출 후 컬럼하여 120 mg의 N-(4-니트로벤질)아크릴아미드(N-(4-nitrobenzyl)acrylamide)를 58% 수율로 얻었다.1-(azidomethyl)-4-nitrobenzene 178 mg (1.00 mmol) and propargyl bromide 156 μL (2.00 mmol), CuSO ₄ 5H ₂ 280 mg (1.1 mmol) of O and 30 mg (0.15 mmol) of sodium ascorbate were mixed, 1 mL of water and 0.5 mL of CH ₂ Cl ₂ were added, and the mixture was incubated at 50 °C.

It was stirred for 5 hours. After completion of the reaction, the extract was extracted three times with 1.5 mL of CH ₂ Cl ₂ and columnarized to obtain 120 mg of N-(4-nitrobenzyl)acrylamide with a yield of 58%.

Through NMR analysis, it was confirmed that N-(4-nitrobenzyl)acrylamide was synthesized (Figures 5a and 5b).

NMR analysis results:

^1H NMR (500 MHz, Chloroform- d ) δ 8.15 - 8.09 (m, 2H), 7.44 - 7.38 (m, 2H), 6.55 (s, 1H), 6.32 (d, J = 16.9 Hz, 1H), 6.17 (ddd, J = 17.0, 10.2, 2.6 Hz, 1H), 5.69 (d, J = 10.1 Hz, 1H), 4.57 (dd, J = 6.2, 2.4 Hz, 2H).

¹³ C NMR (126 MHz, CDCl ₃ ) δ 165.90, 147.24, 145.93, 130.23, 128.31, 127.70, 123.93, 42.92.

Example 6

201 mg (1.00 mmol) of 1-(azidomethyl)-4-(trifluoromethyl)benzene and 156 μL (2.00 mmol) of propargyl bromide mmol), 280 mg (1.1 mmol) of CuSO ₄ 5H ₂ O, and 30 mg (0.15 mmol) of sodium ascorbate were mixed, 1 m of water and 0.5 mL of CH ₂ Cl ₂ were added, and then the mixture. was stirred at 50°C for 5 hours. After completion of the reaction, extraction was performed three times with 1.5 m CH ₂ Cl ₂ and column was used to obtain 130 mg of N-(4-(trifluoromethyl)benzyl)acrylamide at 57% concentration. obtained by yield.

Through NMR analysis, it was confirmed that N-(4-(trifluoromethyl)benzyl)acrylamide was synthesized (FIGS. 6a, 6b).

NMR analysis results:

^1H NMR (500 MHz, Chloroform- d ) δ 7.59 (d, J = 7.8 Hz, 2H), 7.41 (d, J = 7.7 Hz, 2H), 6.35 (d, J = 17.0 Hz, 1H), 6.18 - 6.08 (m, 1H), 5.97 (s, 1H), 5.71 (d, J = 10.3 Hz, 1H), 4.58 (d, J = 6.0 Hz, 2H).

¹³ C NMR (126 MHz, CDCl ₃ ) δ 165.63, 142.33, 130.44, 130.13, 129.87, 128.14, 127.51, 125.86, 125.83, 125.80, 125.77, 125.27, 123.1 1, 43.27, 31.08.

According to the above examples, the method for producing the acrylamide compound and its derivatives of the present invention uses an azido compound that is easy to introduce as a starting material and is easily obtained under mild and controllable reaction conditions without using acids or bases. It can be seen that high purity and high yield of acrylamide can be produced in a one-step reaction using existing materials.

Although specific examples of the method for producing an acrylamide compound and its derivatives according to the present invention have been described so far, it is obvious that various modifications can be made without departing from the scope of the present invention.

Therefore, the scope of the present invention should not be limited to the described embodiments, but should be determined by the claims and equivalents thereof as well as the claims described later.

That is, the above-described embodiments should be understood in all respects as illustrative and not restrictive, and the scope of the present invention is indicated by the claims to be described later rather than the detailed description, and the meaning and scope of the claims and All changes or modified forms derived from the equivalent concept should be construed as falling within the scope of the present invention.

Claims (13)

An azido compound represented by the following formula (1); A propargyl compound represented by the following formula (2); menstruum; and reacting the catalyst,
Method for producing an acrylamide compound represented by the following formula (3):
[Formula 1]

[Formula 2]
.
[Formula 3]

In Formulas 1 and 3, R represents a substituted or unsubstituted alkyl group with 1 to 10 carbon atoms or an aryl group with 3 to 10 ring atoms, and the substituted alkyl group or aryl group is alkyl, alkyloxy, nitro, ester, tri. is substituted with a substituent selected from fluoroalkyl or aryl,
In Formula 2, X is selected from bromine (Br), iodine (I), chlorine (Cl), or tosylate.
delete delete According to paragraph 1,
The propargyl compound is characterized in that it is contained in a ratio of 0.2 to 5 moles relative to the azido compound.
Method for producing acrylamide compounds.
According to paragraph 1,
Characterized in that the solvent contains water (H ₂ O),
Method for producing acrylamide compounds.
According to clause 5,
Characterized in that the solvent is water (H ₂ O),
Method for producing acrylamide compounds.
According to clause 5,
The solvent is dichloromethane (CH ₂ Cl ₂ ), chloroform (CHCl ₃ ), dichloroethane (C ₂ H ₄ C _l2 ), acetone (C ₃ H ₆ O ₂ ), ethanol (C ₂ H ₅ OH), and propanol ( Characterized in that it further comprises any one of C ₃ H ₈ OH),
Method for producing acrylamide compounds.
According to paragraph 1,
The catalyst is characterized in that it is any one of copper sulfate hydrochloride (CuSO ₄ 5H ₂ O), copper iodide (CuI), copper bromide (CuBr), and copper chloride (CuCl).
Method for producing acrylamide compounds.
According to clause 8,
The catalyst is characterized in that it further contains sodium ascorbate,
Method for producing acrylamide compounds.
According to paragraph 1,
Characterized in that the reaction is carried out in a one-pot process,
Method for producing acrylamide compounds.
According to clause 10,
Characterized in that the reaction is carried out at 30 to 80 ° C. for 2 to 24 hours,
Method for producing acrylamide compounds.
delete According to paragraph 1,
Characterized in that the acrylamide compound is a monomer,
Method for producing acrylamide compounds.