CN115584518A - A kind of electrochemical method for preparing N-alkyl amides - Google Patents
A kind of electrochemical method for preparing N-alkyl amides Download PDFInfo
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- 238000002848 electrochemical method Methods 0.000 title description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims abstract description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 24
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000012043 crude product Substances 0.000 claims abstract description 13
- 239000003792 electrolyte Substances 0.000 claims abstract description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000004440 column chromatography Methods 0.000 claims abstract description 10
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 150000004716 alpha keto acids Chemical class 0.000 claims abstract description 5
- -1 amine compound Chemical class 0.000 claims abstract description 4
- 239000012298 atmosphere Substances 0.000 claims abstract description 3
- 238000001704 evaporation Methods 0.000 claims abstract description 3
- 229910002804 graphite Inorganic materials 0.000 claims abstract description 3
- 239000010439 graphite Substances 0.000 claims abstract description 3
- 238000003760 magnetic stirring Methods 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000012046 mixed solvent Substances 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 238000003487 electrochemical reaction Methods 0.000 claims description 2
- 239000003480 eluent Substances 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 5
- 230000001590 oxidative effect Effects 0.000 abstract description 4
- 125000000524 functional group Chemical group 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 229910052723 transition metal Inorganic materials 0.000 abstract description 3
- 150000003624 transition metals Chemical class 0.000 abstract description 3
- 230000003647 oxidation Effects 0.000 abstract description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 26
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 10
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000012512 characterization method Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 4
- VTESCYNPUGSWKG-UHFFFAOYSA-N (4-tert-butylphenyl)hydrazine;hydrochloride Chemical compound [Cl-].CC(C)(C)C1=CC=C(N[NH3+])C=C1 VTESCYNPUGSWKG-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- UASZGGQRDGLTIQ-UHFFFAOYSA-N 2-(4-bromophenyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC=C(Br)C=C1 UASZGGQRDGLTIQ-UHFFFAOYSA-N 0.000 description 1
- ADCUEPOHPCPMCE-UHFFFAOYSA-N 4-cyanobenzoic acid Chemical compound OC(=O)C1=CC=C(C#N)C=C1 ADCUEPOHPCPMCE-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/09—Nitrogen containing compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Abstract
An electrochemical process for the preparation of an N-alkylamide comprising the steps of: in an air atmosphere, adding a fatty amine compound and alpha-keto acid into a reactor at a molar ratio of 1.2, adding an electrolyte of tetrabutylammonium fluoride, and adding dichloromethane and tetrahydrofuran 4: 1; stirring the mixture by a magnetic stirring device to dissolve the mixture, inserting two electrodes, electrifying for 2h by using a graphite electrode as a positive electrode and a platinum sheet electrode as a negative electrode for 8mA, evaporating the solvent under reduced pressure after the reaction is finished to obtain a crude product, and purifying by column chromatography to obtain the N-alkyl amide compound. Compared with the traditional synthesis method, the method has the advantages that the reaction condition is mild, and the reaction can be smoothly carried out at room temperature; the operation is simple, and all the operations can be carried out in an open system; the current is used as an oxidation method in the reaction, so that the pollution of transition metal or chemical oxidant is avoided; easily available raw materials, good functional group compatibility and wide substrate application range.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to an electrochemical method for preparing N-alkylamide.
Background
Amide structure is one of the most basic chemical building blocks found in nature. It constitutes the backbone of biologically important proteins and is present in a large number of synthetic structures (Science 2020,367, 281-285.). Since the interest in polypeptides, i.e., important amide-containing biopolymers in biological organisms, has increased rapidly, methods for efficiently constructing amide bonds have been extensively studied and are one of the most fundamental and important transformations in organic synthesis. Therefore, the synthesis of the N-alkylamide compound has important application and research values.
The methods for synthesizing amide compounds that have been reported so far are mainly carboxylic acid and amine based dehydration condensation reactions that use equivalent amounts of chemical oxidizing agents or condensing agents to promote the reaction. In recent years, electrochemical synthesis has received increasing attention because it avoids the use of catalysts and external oxidants, meeting the requirements of green and sustainable chemistry.
Disclosure of Invention
Aiming at the problems, the invention provides an electrochemical method for preparing N-alkylamide, which has mild reaction conditions and can be smoothly carried out at room temperature; the operation is simple, and all the operations can be carried out in an open system; the reaction uses current as an oxidation method, so that the use of transition metal and chemical oxidant is avoided; the raw materials are easy to obtain, the reaction yield is high, the compatibility of functional groups is good, and the application range of a substrate is wide;
in order to achieve the purpose, the invention provides the following technical scheme: an electrochemical method for preparing N-alkyl sulfoxide imide, which comprises the following steps:
in an air atmosphere, a fatty amine compound and an alpha-keto acid are added into a reactor at a molar ratio of 1.2, an electrolyte of tetrabutylammonium fluoride is added, and dichloromethane and tetrahydrofuran 4: 1; stirring the mixture by a magnetic stirring device to dissolve the mixture, inserting two electrodes, electrifying the positive electrode by a graphite electrode and the negative electrode by a platinum sheet electrode for 8mA for 2h, evaporating the solvent under reduced pressure after the reaction is finished to obtain a crude product, and purifying by column chromatography to obtain the N-alkyl amide compound.
In the step, the reactor is a diaphragm-free electrolytic cell, and the N-alkyl amide compound is prepared through electrochemical reaction, wherein the preparation method comprises the following reaction formula:
in the formula R 1 = benzyl, each substituted alkyl; r 2 = phenyl, substituted phenyl, eachA substituted aromatic heterocyclic compound; the electrolyte is tetrabutylammonium fluoride.
Preferably, the anode electrode plate is a carbon rod electrode, and the cathode electrode plate is a platinum plate electrode.
Preferably, the electrolyte is tetrabutylammonium fluoride with a concentration of 0.05mol/L.
Preferably, in the step, the reaction is carried out under open conditions and room temperature conditions, the power supply used for the reaction is a 30V/3A direct current stabilized power supply, and the electrifying current is 8 milliamperes.
Preferably, the solvent is a mixed solvent of dichloromethane and tetrahydrofuran, and the ratio of dichloromethane to tetrahydrofuran is 4.
Preferably, in the step, the eluent used for column chromatography purification is a mixed solvent of petroleum ether and ethyl acetate, and the volume ratio of petroleum ether to ethyl acetate is 3.
The invention has the beneficial effects that:
1. the invention adopts cheap and easily obtained alpha-keto acid and fatty amine as raw materials, the alpha-keto acid can be prepared from corresponding acetophenone, and the fatty amine is obtained by a commercial way.
2. The method can be operated under the air condition, is not sensitive to water and oxygen, has relatively mild reaction condition and is simple to operate.
3. The invention adopts current as oxidant, has low cost and avoids the pollution of traditional transition metal catalyst or equivalent chemical oxidant.
4. The method can obtain the target product by only one step, and has the advantages of high yield, good functional group compatibility, simple post-treatment and good application potential.
Drawings
FIG. 1 is a hydrogen spectrum of the product obtained in example 1 of the present invention;
FIG. 2 is a carbon spectrum of the product obtained in example 1 of the present invention;
FIG. 3 is a hydrogen spectrum of the product obtained in example 2 of the present invention;
FIG. 4 is a carbon spectrum of the product obtained in example 2 of the present invention;
FIG. 5 is a hydrogen spectrum of the product obtained in example 3 of the present invention;
FIG. 6 is a chart showing a carbon spectrum of a product obtained in example 3 of the present invention;
FIG. 7 is a hydrogen spectrum of the product obtained in example 4 of the present invention;
FIG. 8 is a chart showing a carbon spectrum of a product obtained in example 4 of the present invention;
FIG. 9 is a hydrogen spectrum of the product obtained in example 5 of the present invention;
FIG. 10 is a chart showing a carbon spectrum of a product obtained in example 5 of the present invention;
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings, so that those skilled in the art can better understand the advantages and features of the present invention, and thus the scope of the present invention is more clearly defined. The embodiments described herein are only a few embodiments of the present invention, rather than all embodiments, and all other embodiments that can be derived by one of ordinary skill in the art based on the embodiments described herein are intended to be within the scope of the present invention.
Example 1:
a10 mL diaphragm-free electrolytic cell was equipped with a carbon rod electrode (electrode size: diameter. Phi.6 mm) as an anode and a platinum sheet (size: 10 mm. Times.10 mm. Times.0.1 mm) as a cathode, followed by addition of benzylamine (21.4 mg, 0.20mmol), benzoylformic acid (36.0mg, 0.24mmol), an electrolyte of tetrabutylammonium fluoride (0.25 mmol), 4mL of dichloromethane, 1mL of tetrahydrofuran, and the reaction was stirred at room temperature for 2 hours at a constant current of 8 mA. After the reaction is finished, the solvent is evaporated under reduced pressure to obtain a crude product, and the crude product is purified by column chromatography to obtain 35.9mg of a target product, wherein the yield is 85%. The resulting product has the following structural formula:
the structural characterization data of the resulting product are shown below:
1 H NMR(500MHz,Chloroform-d)δ7.82(d,J＝7.8Hz,2H),7.51(t,J＝7.4 Hz,1H),7.43(t,J＝7.6Hz,2H),7.39-7.29(m,5H),6.66(s,1H),4.65(d,J＝5.7Hz, 2H). 13 C NMR(125MHz,Chloroform-d)δ167.5,138.2,134.4,131.6,128.8,128.6, 127.9,127.6,127.0,44.1.
example 2:
in a 10mL diaphragm-free electrolytic cell equipped with a carbon rod electrode (electrode size: diameter. Phi.6 mm) as an anode and a platinum sheet (size: 10 mm. Times.10 mm. Times.0.1 mm) as a cathode, n-butylamine (14.6 mg, 0.20mmol), benzoylformic acid (36.0mg, 0.24mmol), an electrolyte of tetrabutylammonium fluoride (0.25 mmol), 4mL of dichloromethane, 1mL of tetrahydrofuran, the reaction was stirred at room temperature for 2 hours at a constant current of 8 mA. After the reaction is finished, the solvent is evaporated under reduced pressure to obtain a crude product, and the crude product is purified by column chromatography to obtain 26.2mg of a target product, wherein the yield is 74%. The resulting product has the following structural formula:
the structural characterization data of the resulting product are shown below:
1 H NMR(500MHz,Chloroform-d)δ7.78(d,J＝7.6Hz,2H),7.46(t,J＝7.3 Hz,1H),7.39(t,J＝7.6Hz,2H),6.60(s,1H),3.42(q,J＝6.7Hz,2H),1.58(p,J＝ 7.3Hz,2H),1.38(tt,J＝11.0,5.5Hz,2H),0.94(t,J＝7.4Hz,3H). 13 C NMR(125 MHz,Chloroform-d)δ167.7,134.9,131.2,128.5,126.9,39.8,31.7,20.2,13.8.
example 3:
a10 mL diaphragm-free electrolytic cell was equipped with a carbon rod electrode (electrode size: diameter. Phi.6 mm) as an anode and a platinum plate (size: 10 mm. Times.10 mm. Times.0.1 mm) as a cathode, followed by addition of 2-thiophenemethylamine (22.6 mg,0.20 mmol), benzoylformic acid (36.0 mg, 0.24mmol), an electrolyte of tetrabutylammonium fluoride (0.25 mmol), dichloromethane (4 mL), tetrahydrofuran (1 mL), and reaction was stirred at room temperature for 2 hours at a constant current of 8 mA. After the reaction is finished, the solvent is evaporated under reduced pressure to obtain a crude product, and the crude product is purified by column chromatography to obtain 28.2mg of a target product, wherein the yield is 65%. The resulting product has the following structural formula:
the structural characterization data of the resulting product are shown below:
1 H NMR(500MHz,Chloroform-d)δ7.80(d,J＝7.6Hz,2H),7.51(t,J＝7.5 Hz,1H),7.42(t,J＝7.6Hz,2H),7.25(d,J＝5.1Hz,1H),7.08-6.90(m,2H),6.80(s, 1H),4.80(d,J＝5.6Hz,2H). 13 C NMR(125MHz,Chloroform-d)δ167.3,140.9, 134.2,131.6,128.6,127.1,127.0,126.2,125.3,38.8.
example 4:
a10 mL diaphragm-free electrolytic cell was equipped with a carbon rod electrode (electrode size: diameter. Phi.6 mm) as an anode and a platinum plate (size: 10 mm. Times.10 mm. Times.0.1 mm) as a cathode, followed by addition of benzylamine (21.4 mg, 0.20mmol), p-bromobenzoyl formic acid (55.0 mg, 0.24mmol), an electrolyte of tetrabutylammonium fluoride (0.25 mmol), dichloromethane (4 mL), tetrahydrofuran (1 mL), and the reaction was stirred at room temperature for 2 hours at a constant current of 8 mA. After the reaction is finished, the solvent is evaporated under reduced pressure to obtain a crude product, and the crude product is purified by column chromatography to obtain 31.2mg of a target product, wherein the yield is 74%. The resulting product has the following structural formula:
the structural characterization data of the resulting product are shown below:
1 H NMR(500MHz,Chloroform-d)δ7.72-7.63(m,2H),7.55(dd,J＝8.6,2.1 Hz,2H),7.41-7.29(m,5H),6.63(s,1H),4.62(d,J＝5.7Hz,2H). 13 C NMR(125 MHz,Chloroform-d)δ166.5,138.0,133.2,131.8,128.8,128.6,127.9,127.7,126.3, 44.2.
example 5:
a10 mL diaphragm-free electrolytic cell was equipped with a carbon rod electrode (electrode size: diameter. Phi.6 mm) as an anode and a platinum sheet (size: 10 mm. Times.10 mm. Times.0.1 mm) as a cathode, followed by addition of benzylamine (21.4 mg, 0.20mmol), p-cyanobenzoic acid (42.0mg, 0.24mmol), an electrolyte of tetrabutylammonium fluoride (0.25 mmol), dichloromethane (4 mL), tetrahydrofuran (1 mL), and the reaction was stirred at room temperature for 2 hours at a constant current of 8 mA. After the reaction is finished, the solvent is evaporated under reduced pressure to obtain a crude product, and the crude product is purified by column chromatography to obtain 25.5mg of a target product, wherein the yield is 54%. The resulting product has the following structural formula:
the structural characterization data of the resulting product are shown below:
1 H NMR(500MHz,Chloroform-d)δ7.91(d,J＝7.9Hz,2H),7.75(d,J＝7.9 Hz,2H),7.37(hept,J＝7.3Hz,5H),6.51(s,1H),4.67(d,J＝5.6Hz,2H). 13 C NMR (125MHz,Chloroform-d)δ165.6,138.3,137.5,132.5,129.0,128.0,128.0,127.7, 118.0,115.2,44.5。
Claims (6)
1. an electrochemical process for the preparation of an N-alkylamide, characterized in that: the preparation method comprises the following steps: in an air atmosphere, adding a fatty amine compound and alpha-keto acid into a reactor at a molar ratio of 1.2, adding an electrolyte of tetrabutylammonium fluoride, and adding dichloromethane and tetrahydrofuran 4: 1; stirring the mixture by using a magnetic stirring device to dissolve the mixture, inserting two electrodes, electrifying for 2 hours by using a graphite electrode as a positive electrode and a platinum sheet electrode as a negative electrode and electrifying for 8mA, evaporating the solvent under reduced pressure after the reaction is finished to obtain a crude product, and purifying by using column chromatography to obtain an N-alkyl amide compound;
in the step, the reactor is a diaphragm-free electrolytic cell, and the N-alkyl amide compound is prepared through electrochemical reaction, wherein the reaction equation is as follows:
in the formula R 1 = benzyl, each substituted alkyl; r 2 = phenyl group, substituted aromatic heterocyclic compound; the electrolyte is tetrabutylammonium fluoride.
2. An electrochemical process for the preparation of an N-alkylamide according to claim 1, characterized in that: the anode electrode plate is a carbon rod electrode, and the cathode electrode plate is a platinum plate electrode.
3. An electrochemical process for the preparation of an N-alkylamide according to claim 1, characterized in that: the electrolyte is tetrabutylammonium fluoride, and the concentration of the tetrabutylammonium fluoride is 0.05mol/L.
4. An electrochemical process for the preparation of an N-alkyl amide as claimed in claim 1, wherein: in the step, the reaction is carried out under the open condition and the room temperature condition, the power supply used for the reaction is a 30V/3A direct current stabilized power supply, and the electrifying current is 8 milliamperes.
5. An electrochemical process for the preparation of an N-alkyl amide as claimed in claim 1, wherein: the solvent is a mixed solvent of dichloromethane and tetrahydrofuran, and the ratio of the dichloromethane to the tetrahydrofuran is 4.
6. An electrochemical process for the preparation of an N-alkylamide according to claim 1, characterized in that: in the step, an eluent used for column chromatography purification is a mixed solvent of petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 3.
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