CN113979885B - Method for synthesizing amide compounds - Google Patents
Method for synthesizing amide compounds Download PDFInfo
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- CN113979885B CN113979885B CN202111337167.3A CN202111337167A CN113979885B CN 113979885 B CN113979885 B CN 113979885B CN 202111337167 A CN202111337167 A CN 202111337167A CN 113979885 B CN113979885 B CN 113979885B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
Abstract
The invention discloses a method for synthesizing amide compounds, which comprises the following steps: adding solvent, thioacetic acid and amine into a reaction container, and reacting for 6-15 hours at room temperature under the air atmosphere to obtain a reaction solution; and (3) carrying out post-treatment on the reaction liquid to obtain the amide compound. The invention has the advantages that: (1) the reaction does not require catalysts or other additives; (2) the application range of the reaction substrate is wide; (3) water can be used as a solvent, so that the method is environment-friendly; (4) The reaction condition is simple, the yield is high, and the reaction can be amplified to gram-grade reaction.
Description
Technical Field
The invention relates to a method for synthesizing amide compounds, belonging to the field of green organic synthesis.
Background
Amidation is one of the most important basic reactions in organic chemistry, and amide compounds are organic compounds of great research value, with amide bonds being the ubiquitous chemical raw materials and ubiquitous structural basis in natural products, pharmaceuticals and agrochemicals.
Extensive research has been conducted on the synthesis of amides, traditional methods utilizing amidation of carboxylic acids or carboxylic acid derivatives with amines, and the classical synthetic route generally requires the preparation of reactive intermediates, such as esters, anhydrides or acid chlorides, followed by reaction with nucleophilic amines. The use of thioacid as an amidation reagent has good stability and the reaction conditions for amidation are relatively mild, so that a method for preparing an amide by reacting an amine with thioacid has been attracting attention.
In 2013, hosahudea n.gopi et al synthesized amides using an acylation reaction of amine and thioacetic acid under the catalysis of 30mol% copper sulfate (j.org.chem.2013, 78, 5550-5555), the reaction formula is as follows:
2016, tan et al utilized potassium thiosulfate and an amine in photosensitizer Ru (bpy) 3 Cl 2 Is catalyzed by ACS catalyst 2016,6, 1732-1736) in the presence of an amide, the reaction being as follows:
in 2017, miraki et al found a superparamagnetic nanocatalyst (Fe 3 O 4 GAA-Cu (II) facilitates the quantitative N-acylation of various amines with equimolar amounts of thioacetic acid to give amides (Appl Organometal Chem,2017, 31, e 3744) of the following formula:
in 2020, papu Biswas et al used 3, 6-bis (pyridin-2-yl) -1,2,4, 5-tetrazine (pytz) to catalyze the formation of amide bonds from thioacetic acid and an amine to synthesize an amide, (Tetrahedron Letters,2020, 61, 152272) of the formula:
in 2018, papu biswans et al utilized CdS nanoparticles (cdspps) as a photocatalyst, and amidated amine with thioacid under visible light radiation to synthesize amide, (Appl Organometal Chem,2018, 32, e 4199), the reaction formula is as follows:
in 2019, guan et al were under an air atmosphere, the thio fatty acids could be electrooxidized to disulfides, which in turn reacted with amines to form the corresponding amides, (ChemSusChem 2019,12,2570-2575), of the formula:
in 2020, song et al used Mes-Acr-MeBF4 as a photocatalyst and catalyzed thioacetic acid and amine by blue light irradiation to perform amidation reaction to synthesize amide, (Org. Lett.2020,22, 371-375) with the following reaction formula:
in 2020, li et al studied the synthesis of amides by reacting potassium thioacetate with various anilines to form N-phenylacetamides using MSP-CB [8] -c as a photooxidation reduction catalyst, (ACS appl. Polym. Mater.2020,2, 4885-4892) of the formula:
as described above, there are many methods for synthesizing amides, and methods for synthesizing acetamides using thioacetic acid and various amines are widely used. However, in the disclosed method, means such as photochemistry, electrochemistry, noble metal catalysis and the like are commonly used, or an organic solvent with high toxicity is used, or the experiment is complicated in the operation process. Therefore, there is still a need for continued research to develop simple and efficient methods for synthesizing amide compounds.
Disclosure of Invention
The invention aims to: aiming at the defects of the prior art, the invention discloses a method for synthesizing amide compounds, which takes thioacetic acid and various primary amines or secondary amines as raw materials, does not need catalysts and additives, has simple conditions, simple reaction process and high yield, and can be amplified to gram-scale reaction.
The reaction formula of the invention is as follows:
the technical scheme is as follows: a method for synthesizing an amide compound, comprising the steps of:
adding solvent, thioacetic acid and amine shown in formula (1) into a reaction container, and reacting for 6-15 hours at room temperature under the air atmosphere to obtain a reaction solution;
post-treating the reaction solution to obtain an amide compound shown in a formula (2), wherein:
the molar ratio of the thioacetic acid to the amine shown in the formula (1) is 1-3: 1, a step of;
the amount of the solvent is 2 to 5g/mmol based on the molar amount of the amine represented by the formula (1);
R 1 is one of hydrogen, alkyl and aryl;
R 2 is phenyl, substituted phenyl, heterocycle, naphthyl, alkyl or allylOne of the two;
further, R 1 When the alkyl is alkyl, the alkyl is one of methyl, ethyl, isopropyl and butyl.
Further, R 2 When the phenyl is substituted, the substituent of the substituted phenyl is one of alkyl, halogen, acetyl, ester and alkoxy.
R 2 When the heterocyclic ring is heterocyclic, the heterocyclic ring is one of pyridyl, furyl and thienyl.
Further, the solvent is any one of dioxane, acetonitrile, toluene, water, dimethyl sulfoxide, dichloromethane and tetrahydrofuran.
Still further, the solvent is water.
Further, the post-treatment is column chromatography separation or preparative thin layer chromatography separation.
The invention uses thioacetic acid as acyl source, which has strong polarization effect of C-S bond, greatly enhances electrophilic activity and reaction capability with amine.
The beneficial effects are that: the invention has the advantages that:
(1) No catalyst or other additives are needed for the reaction;
(2) The application range of the reaction substrate is wide;
(3) Water can be used as a solvent, so that the method is environment-friendly;
(4) The reaction condition is simple, the yield is high, and the reaction can be amplified to gram-grade reaction.
Description of the drawings:
FIG. 1 is a flow chart of a method for synthesizing an amide compound according to the present invention.
The specific embodiment is as follows:
the following detailed description of specific embodiments of the invention.
The present invention is specifically described below with reference to specific embodiments, but these examples are not intended to limit the actual scope of the present invention in any way, nor are they intended to limit the scope of the present invention.
Example 1
Aniline (0.3 mmol), thioacetic acid (0.45 mmol), and an aqueous solvent (H) were added sequentially to the reaction tube at room temperature under an air atmosphere 2 O) (1 mL) was reacted at room temperature for 12 hours, and after the completion of the reaction, the product was isolated by column chromatography in 96% yield.
The results of the nuclear magnetic characterization of the product are as follows: 1 H NMR(400MHz,DMSO)δ9.92(s,1H),7.58(d,J＝5.8Hz,2H),7.27(dd,J＝7.2,5.3Hz,2H),7.01(t,J＝5.7Hz,1H),2.04(d,J＝3.3Hz,3H).
example 2
4-methylaniline (0.3 mmol), thioacetic acid (0.45 mmol), and water solvent (H) were sequentially added to the reaction tube at room temperature under an air atmosphere 2 O) (1 mL) was reacted at room temperature for 12 hours, and after the completion of the reaction, the product was isolated by column chromatography in 99% yield.
The results of the nuclear magnetic characterization of the product are as follows: 1 H NMR(500MHz,DMSO)δ9.79(s,1H),7.44(d,J＝8.3Hz,2H),7.06(d,J＝8.2Hz,2H),2.22(s,3H),2.00(s,3H).
example 3
4-Methoxyaniline (0.3 mmol), thioacetic acid (0.45 mmol), and an aqueous solvent (H) were sequentially added to the reaction tube at room temperature under an air atmosphere 2 O) (1 mL) was reacted at room temperature for 12 hours, and after the completion of the reaction, the product was isolated by column chromatography in 97% yield.
Product nuclear magnetic characterizationThe results were as follows: 1 H NMR(500MHz,DMSO)δ9.85(s,1H),7.60–7.53(m,2H),6.98–6.92(m,2H),3.80(s,3H),2.09(d,J＝9.0Hz,3H).
example 4
4-fluoroaniline (0.3 mmol), thioacetic acid (0.45 mmol) and water solvent (H) were successively added to the reaction tube at room temperature under an air atmosphere 2 O) (1 mL) was reacted at room temperature for 12 hours, and after the completion of the reaction, the product was isolated by column chromatography in 90% yield.
The results of the nuclear magnetic characterization of the product are as follows: 1 H NMR(400MHz,DMSO)δ9.95(s,1H),7.56(dt,J＝9.2,5.4Hz,2H),7.13–7.05(m,2H),2.01(d,J＝5.6Hz,3H).
example 5
4-Chloroaniline (0.3 mmol), thioacetic acid (0.45 mmol), and water solvent (H) were sequentially added to the reaction tube at room temperature under an air atmosphere 2 O) (1 mL) was reacted at room temperature for 12 hours, and after the completion of the reaction, the product was isolated by column chromatography in 99% yield.
The results of the nuclear magnetic characterization of the product are as follows: 1 H NMR(500MHz,DMSO)δ10.05(s,1H),7.61(d,J＝8.8Hz,2H),7.35-7.31(m,2H),2.04(s,3H).
example 6
2-aminophenol (0.3 mmol), thioacetic acid (0.45 mmol), and an aqueous solvent (H) were sequentially added to the reaction tube at room temperature under an air atmosphere 2 O) (1 mL) was reacted at room temperature for 12 hours, and after the completion of the reaction, the product was isolated by column chromatography in 99% yield.
The results of the nuclear magnetic characterization of the product are as follows: 1 H NMR(500MHz,DMSO)δ9.74(s,1H),9.31(s,1H),7.68(d,J＝7.7Hz,1H),6.94(dd,J＝11.1,4.1Hz,1H),6.88–6.84(m,1H),6.79–6.73(m,1H),2.10(s,3H).
example 7
1-naphthylamine (0.3 mmol), thioacetic acid (0.45 mmol), and an aqueous solvent (H) were sequentially added to the reaction tube at room temperature under an air atmosphere 2 O) (1 mL) was reacted at room temperature for 12 hours, and after the completion of the reaction, the product was isolated by column chromatography in 99% yield.
The results of the nuclear magnetic characterization of the product are as follows: 1 H NMR(500MHz,DMSO)δ9.90(s,1H),8.08(d,J＝7.7Hz,1H),7.93(d,J＝7.1Hz,1H),7.72(dd,J＝27.3,7.7Hz,2H),7.57–7.51(m,2H),7.48(t,J＝7.8Hz,1H),2.19(s,3H).
example 8
N-methyl-p-toluidine (0.3 mmol), thioacetic acid (0.45 mmol), and an aqueous solvent (H) were sequentially added to the reaction tube at room temperature under an air atmosphere 2 O) (1 mL) was reacted at room temperature for 12 hours, and after the completion of the reaction, the product was isolated by column chromatography in 92% yield.
The results of the nuclear magnetic characterization of the product are as follows: , 1 H NMR(400MHz,DMSO)δ7.26–7.16(m,3H),3.10(s,2H),2.32(s,2H),1.73(s,2H).
example 9
3, 5-difluoroaniline (0.3 mmol), thioacetic acid (0.45 mmol), and water solvent (H were added sequentially to the reaction tube at room temperature under an air atmosphere 2 O) (1 mL) was reacted at room temperature for 12 hours, and after the completion of the reaction, the product was isolated by column chromatography in 92% yield.
The results of the nuclear magnetic characterization of the product are as follows: , 1 H NMR(400MHz,DMSO)δ10.30(s,1H),7.28(d,J＝8.1Hz,2H),6.85(t,J＝9.3Hz,1H),2.06(s,3H).
example 10
3, 5-difluoroaniline (0.3 mmol), thioacetic acid (0.45 mmol), and water solvent (H were added sequentially to the reaction tube at room temperature under an air atmosphere 2 O) (1 mL) was reacted at room temperature for 12 hours, and after the completion of the reaction, the product was isolated by column chromatography in 90% yield.
The results of the nuclear magnetic characterization of the product are as follows: , 1 H NMR(500MHz,DMSO)δ7.67–7.61(m,2H),7.56(dd,J＝17.0,9.7Hz,1H),7.40(d,J＝7.6Hz,2H),6.10(ddt,J＝16.6,10.5,6.3Hz,1H),5.40–5.26(m,2H),4.54(d,J＝6.2Hz,2H),2.10(s,3H).
example 11
A method for synthesizing an amide compound, comprising the steps of:
adding a solvent, thioacetic acid and amine shown in a formula (1) into a reaction container, and reacting for 6 hours at room temperature under the air atmosphere to obtain a reaction solution;
post-treating the reaction solution to obtain an amide compound shown in a formula (2), wherein:
the molar ratio of the thioacetic acid to the amine shown in the formula (1) is 1:1, a step of;
the amount of the solvent used was 2g/mmol based on the molar amount of the amine represented by the formula (1);
R 1 is hydrogen;
R 2 is phenyl;
further, the solvent is dioxane.
Still further, the solvent is water.
Further, the post-treatment is column chromatography separation.
Example 12
A method for synthesizing an amide compound, comprising the steps of:
adding a solvent, thioacetic acid and amine shown in a formula (1) into a reaction container, and reacting for 15 hours at room temperature under the air atmosphere to obtain a reaction solution;
post-treating the reaction solution to obtain an amide compound shown in a formula (2), wherein:
the molar ratio of the thioacetic acid to the amine shown in the formula (1) is 3:1, a step of;
the amount of the solvent used was 5g/mmol based on the molar amount of the amine represented by the formula (1);
R 1 is aryl;
R 2 is allyl;
further, the solvent is water.
Further, the post-treatment is preparative thin layer chromatography.
Example 13
A method for synthesizing an amide compound, comprising the steps of:
adding a solvent, thioacetic acid and amine shown in a formula (1) into a reaction container, and reacting for 12 hours at room temperature under the air atmosphere to obtain a reaction solution;
post-treating the reaction solution to obtain an amide compound shown in a formula (2), wherein:
the molar ratio of the thioacetic acid to the amine shown in the formula (1) is 2:1, a step of;
the amount of the solvent used was 3g/mmol based on the molar amount of the amine represented by the formula (1);
R 1 is hydrogen;
R 2 is methyl;
further, the solvent is acetonitrile.
Further, the post-treatment is column chromatography separation.
Examples 14 to 18
Substantially the same as in example 10, the difference is only that: substituent R 1 Different from
| R 1 | |
| Example 14 | Aryl group |
| Example 15 | Methyl group |
| Example 16 | Ethyl group |
| Example 17 | Isopropyl group |
| Example 18 | Butyl group |
Examples 19 to 36
Substantially the same as in example 10, the difference is only that: substituent R 2 Different from
Examples 37 to 43
Substantially the same as in example 10, the difference is only that: the solvents are different:
| solvent(s) | |
| Example 37 | Tetrahydrofuran (THF) |
| Example 38 | Dichloromethane (dichloromethane) |
| Example 39 | Dimethyl sulfoxide |
| Example 40 | Water and its preparation method |
| Example 41 | Toluene (toluene) |
| Example 42 | Acetonitrile |
| Example 43 | Dioxaalkane |
The embodiments of the present invention have been described in detail. However, the present invention is not limited to the above-described embodiments, and various modifications may be made within the knowledge of those skilled in the art without departing from the spirit of the present invention.
Claims (4)
1. A method for synthesizing an amide compound, comprising the steps of:
adding solvent, thioacetic acid and amine shown in formula (1) into a reaction container, and reacting for 6-15 hours at room temperature under the air atmosphere to obtain a reaction solution;
post-treating the reaction solution to obtain an amide compound shown in a formula (2), wherein:
the molar ratio of the thioacetic acid to the amine shown in the formula (1) is 1-3: 1, a step of;
the amount of the solvent is 2 to 5g/mmol based on the molar amount of the amine represented by the formula (1);
R 1 is one of hydrogen, alkyl and aryl;
R 2 is one of phenyl, substituted phenyl, heterocycle, naphthyl, alkyl and allyl;
wherein:
the solvent is water and no catalyst is needed for the reaction.
2. A method for synthesizing an amide compound as claimed in claim 1, wherein R 1 When the alkyl is alkyl, the alkyl is one of methyl, ethyl, isopropyl and butyl.
3. A method for synthesizing an amide compound as claimed in claim 1, wherein R 2 When the phenyl is substituted, the substituent of the substituted phenyl is one of alkyl, halogen, acetyl, ester and alkoxy;
R 2 when the heterocyclic ring is heterocyclic, the heterocyclic ring is one of pyridyl, furyl and thienyl.
4. The method for synthesizing an amide compound according to claim 1, wherein the post-treatment is column chromatography or preparative thin layer chromatography.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104961644A (en) * | 2015-05-20 | 2015-10-07 | 上海交通大学 | Method used for preparing N-aryl amide compound |
| CN107056567A (en) * | 2017-06-06 | 2017-08-18 | 温州大学 | A kind of new method of synthesis N substitute amide derivatives |
| CN110698360A (en) * | 2019-10-30 | 2020-01-17 | 大连理工大学 | Method for preparing amide under induction of visible light without participation of metal |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104961644A (en) * | 2015-05-20 | 2015-10-07 | 上海交通大学 | Method used for preparing N-aryl amide compound |
| CN107056567A (en) * | 2017-06-06 | 2017-08-18 | 温州大学 | A kind of new method of synthesis N substitute amide derivatives |
| CN110698360A (en) * | 2019-10-30 | 2020-01-17 | 大连理工大学 | Method for preparing amide under induction of visible light without participation of metal |
Non-Patent Citations (4)
| Title |
|---|
| 3,6-Di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) catalysed metal-free amide bond formation from thioacids and amines at room temperature;Suvendu Samanta et al.;《Tetrahedron Letters》;第152272(1-5)页 * |
| Suvendu Samanta et al..3,6-Di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) catalysed metal-free amide bond formation from thioacids and amines at room temperature .《Tetrahedron Letters》.2020,第152272(1-5)页. * |
| Visible Light-Induced Amide Bond Formation;Wangze Song et al.;《Org. Lett.》;第371-375页 * |
| 可见光催化酰胺类化合物的绿色合成;董锟;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;第B016-387页 * |
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