Method for catalyzing synthesis of n-alkylated amide compounds from alcohols and nitriles by nitrogen-carbon material

Abstract

The application belongs to the technical field of organic synthesis chemistry, and discloses a method for synthesizing N-alkylated amide compounds from alcohols and nitriles by using nitrogen-carbon material as a catalyst. The nitrogen-carbon material prepared by direct pyrolysis is used as a heterogeneous catalyst, potassium hydroxide is used as an additive, toluene is used as a solvent in an air atmosphere, and alcohols and nitriles are used as raw materials to realize the synthesis of N-alkylated amide compounds. Compared with existing synthesis technologies, the method does not need to add other additives such as soluble metal salts and ligands, the catalyst is easy to separate from the product, the catalyst can be recycled and reused, the operation is simple, and the reaction process is economical and efficient.

Description

Technical Field

[0001] This invention belongs to the field of organic synthetic chemistry technology and discloses a method for preparing N-benzylbenzamide and its derivatives by catalyzing benzyl alcohol and benzonitrile with a heterogeneous catalyst. Technical Background

[0002] Amides are important chemical substances widely found in biological macromolecules and are core structural units of many bioactive molecules. Amides can be used as solvents, raw materials for industrial products such as plastics and coatings, and in the manufacture of pesticides, pharmaceuticals, and cosmetics. The Ritter reaction is one of the most important reactions for forming carbon-nitrogen bonds and is widely used to prepare N-alkylamides. First reported by John Ritter in 1948, it involves the condensation of compounds such as alcohols that readily form carbocations with nitriles in the presence of strong acids, followed by hydrolysis to form amides. A drawback of this reaction is the harshness of the reaction conditions, requiring the use of corrosive sulfuric acid. To improve the method, various other catalysts have been used to replace sulfuric acid, such as Fe(ClO4)3-SiO2 and Fe... 3+ -Montmorilonite, refluxed formic acid, R2O5-SiO2, Ca(HSO4)2, perfluorosulfonic acid resin, and silica-grafted sulfuric acid. In recent years, transition metal-catalyzed dehydrogenation coupling and direct coupling of alcohols and nitriles have been developed for the preparation of N-alkylated amide products. However, these methods require complex metal coordination complexes, suffer from poor product selectivity, and have drawbacks such as difficulty in catalyst recycling. Therefore, developing a safe, simple, economical, and efficient method for amide synthesis is crucial. Summary of the Invention

[0003] To overcome the aforementioned problems, this invention provides a method for synthesizing N-benzylbenzamide compounds using carbon-nitrogen materials as heterogeneous catalysts, potassium hydroxide as an additive, toluene as a solvent in an air atmosphere, and benzyl alcohol and benzonitrile as raw materials.

[0004] The reaction steps for synthesizing N-benzylbenzamide and its derivatives involved in this invention are as follows: alcohols, nitriles, potassium hydroxide, mesoporous nitrogen-carbon catalyst (NC-700), and toluene involved in the reaction are added sequentially to a reaction tube, and the reaction is carried out in a heater at a temperature above 140°C under magnetic stirring. After the reaction is completed, the mixture is centrifuged, filtered, and the supernatant is collected. The crude product is then separated and purified by thin-layer chromatography to finally obtain N-benzylbenzamide and its derivatives.

[0005]

[0006] Ar1 and Ar2 are each independently selected from any one of aryl, heteroaryl, substituted aryl, and substituted heteroaryl; the aryl is selected from at least one of phenyl and naphthyl; the heteroaryl is selected from at least one of pyrrole, furanyl, thiophene, pyrazolyl, and imidazolyl; the substituents in the substituted aryl and substituted heteroaryl are each independently selected from at least one of methyl, methoxy, chlorine, and bromine;

[0007] The molar ratio of alcohols to nitriles is 1:2; the molar ratio of alcohols to potassium hydroxide is 1:2; and the amount of alcohol in toluene is 0.1 mmol / mL.

[0008] Furthermore, the mesoporous nitrogen-carbon catalyst NC-T-4 was prepared by pyrolysis using o-phenylenediamine as a precursor to provide nitrogen source.

[0009] Furthermore, the reaction time is more than 2 hours; preferably, the reaction is carried out at 150°C for 5 hours.

[0010] The specific preparation method of NC-T-4 mesoporous nitrogen-carbon catalyst is as follows:

[0011] First, o-phenylenediamine was dissolved in ethanol and distilled water at a ratio of 75:25. Then, a certain amount of dilute nitric acid solution was added to adjust the pH to 2–6. Next, silica sol was added while stirring, and after stirring for 30 minutes, 30 wt% hydrogen peroxide was added dropwise at room temperature. The solution was then stirred further at room temperature for 24 hours. The solution was then evaporated in a water bath (90°C) to remove water, yielding a solid material. The solid material was then pyrolyzed in nitrogen at a rate of 3°C / min for two hours at a given temperature of 80 mL / min. The prepared material was treated with 10 wt% HF solution at room temperature for 12 hours to remove silica. It was then centrifuged and washed with distilled water as much as possible until neutral, and dried at 100°C. The final product of nitrogen-doped carbon was denoted as NC-T-2–6, where T is the pyrolysis temperature and 2–6 indicates the pH value was adjusted to 2–6.

[0012] Furthermore, the pyrolysis temperature is 500–700℃; preferably, the pyrolysis temperature is 700℃.

[0013] Furthermore, it is preferable to adjust the pH to 4.

[0014] Furthermore, the mass-to-volume ratio of o-phenylenediamine to silica sol is 1.08 g: 5 mL; the volume ratio of silica sol to hydrogen peroxide is 1:3 to 6.

[0015] Compared with the prior art, the present invention has the following technical advantages:

[0016] (1) The present invention uses nitrogen-carbon materials as heterogeneous catalysts to achieve the synthesis of products generated by the reaction of alcohol and nitrile under the condition of no metal presence.

[0017] (2) The product of the present invention has high selectivity and no multiple by-products are generated. Furthermore, the present invention does not require high temperature and high pressure and can generate the product in an air atmosphere, providing a reaction path that is highly atom-economical, green and simple. Attached Figure Description

[0018] Figure 1 It is the target product N-benzylbenzamide of Example 1. 1 H-NMR spectrum.

[0019] Figure 2 It is the target product N-benzyl-4-methylbenzamide of Example 2. 1 H-NMR spectrum.

[0020] Figure 3 It is the target product N-benzyl-4-methoxybenzamide of Example 3. 1 H-NMR spectrum.

[0021] Figure 4 It is the target product N-benzyl-4-chlorobenzamide of Example 4. 1 H-NMR spectrum.

[0022] Figure 5 It is the target product N-benzyl-3-bromobenzamide of Example 5. 1 H-NMR spectrum.

[0023] Figure 6 It is the target product N-benzyl-2-naphthylcarboxamide of Example 6. 1 H-NMR spectrum.

[0024] Figure 7 It is the target product N-benzylthiophene-2-carboxamide of Example 7. 1 H-NMR spectrum.

[0025] Figure 8 It is the target product N-(4-methoxybenzyl)benzamide of Example 8. 1 H-NMR spectrum.

[0026] Figure 9 It is the target product N-(thiophene-2-methyl)benzamide of Example 9. 1 H-NMR spectrum. Specific implementation methods

[0027] The following examples will help to illustrate the invention, but are not intended to limit its scope.

[0028] The specific preparation method of NC-T-4 catalyst is as follows:

[0029] First, o-phenylenediamine (10 mmol, 1.08 g) was dissolved in ethanol and distilled water at a ratio of 75:25. Then, a certain amount of dilute nitric acid solution was added to adjust the pH to 4. Next, 5 mL of silica sol was added while stirring, and after stirring for 30 minutes, 20 mL of 30 wt% hydrogen peroxide was added dropwise at room temperature. The solution was then stirred further at room temperature for 24 hours. The solution was then evaporated in a water bath (90 °C) to remove water, yielding a solid material. Pyrolysis was performed at a given temperature in nitrogen at a rate of 80 mL / min for two hours, with a heating rate of 3 °C / min. The prepared material was treated with a 10 wt% HF solution at room temperature for 12 hours to remove silica. Then, it was centrifuged and washed with distilled water as much as possible until neutral, and dried at 100 °C. The final product of nitrogen-doped carbon was denoted as NC-T-4, where T is the pyrolysis temperature and 4 indicates that the pH was adjusted to 4. Catalysts NC-700-4, NC-700-2, NC-700-6, NC-500-4, and NC-600-4 were prepared.

[0030] Table 1 shows the structural parameters of the NC-700-4:

[0031] Table 1:

[0032]

[0033] Example 1:

[0034] 10 mg of NC-700-4 catalyst, 0.2 mmol of benzyl alcohol, 0.4 mmol of benzonitrile, and 0.4 mmol of potassium hydroxide were added to a 10 mL reaction tube. 2 mL of toluene was added under air atmosphere, and the mixture was stirred in a heater at 150 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, centrifuged, and the supernatant was used to determine the conversion and selectivity using gas chromatography. The final calculated yield of the product was 91.0%. The filtered reaction solution was purified by thin-layer chromatography using petroleum ether and ethyl acetate as developing solvents to obtain the product. The characterization data of the product are as follows:

[0035] N-benzylbenzamide: 1 H NMR (400MHz, CDCl3) δ7.79 (dd, J=7.5, 1.7Hz,

[0036] 2H),7.55–7.47(m,1H),7.43(dd,J=8.3,6.7Hz,2H),7.36(d,J=4.3Hz,4H),6.43(s,1H),4.65(d,J=5.6Hz,2H).

[0037] The reaction structure is as follows:

[0038]

[0039] Example 2:

[0040] 10 mg of NC-700-4 catalyst, 0.2 mmol of p-methylbenzyl alcohol, 0.4 mmol of benzonitrile, and 0.4 mmol of potassium hydroxide were added to a 10 mL reaction tube. 2 mL of toluene was added under air atmosphere, and the mixture was stirred in a heater at 150 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, centrifuged, and the supernatant was used to determine the conversion and selectivity using gas chromatography. The final calculated yield of the product was 46.7%. The filtered reaction solution was purified by thin-layer chromatography using petroleum ether and ethyl acetate as developing solvents to obtain the product. The characterization data of the product are as follows:

[0041] N-benzyl-4-methylbenzamide: 1 H NMR (400MHz, CDCl3) δ7.78 (d, J=7.0Hz,

[0042] 2H), 7.50 (t, J = 7.4Hz, 1H), 7.42 (t, J = 7.4Hz, 2H), 7.17 (d, J = 7.8Hz, 2H), 6.37 (s, 1H), 4.61 (d, J = 5.5Hz, 3H), 2.35 (s, 4H).

[0043] The reaction structure is as follows:

[0044]

[0045] Example 3:

[0046] 10 mg of NC-700-4 catalyst, 0.2 mmol of p-methoxybenzyl alcohol, 0.4 mmol of benzonitrile, and 0.4 mmol of potassium hydroxide were added to a 10 mL reaction tube. 2 mL of toluene was added under air atmosphere, and the mixture was stirred in a heater at 150 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, centrifuged, and the supernatant was used to determine the conversion and selectivity using gas chromatography. The final calculated yield of the product was 45.0%. The filtered reaction solution was purified by thin-layer chromatography using petroleum ether and ethyl acetate as developing solvents to obtain the product. The characterization data of the product are as follows:

[0047] N-benzyl-4-methoxybenzamide: 1H NMR (400MHz, CDCl3) δ7.82–7.74(m,2H),7.50(t,J=7.4Hz,1H),7.44(d,J=7.7Hz,2H),7.3 0(d,J=8.5Hz,2H),6.89(d,J=8.6Hz,2H),6.32(s,1H),4.59(d,J=5.4Hz,2H),3.81(s,3H).

[0048] The reaction structure is as follows:

[0049]

[0050] Example 4:

[0051] 10 mg of NC-700-4 catalyst, 0.2 mmol of p-chlorobenzyl alcohol, 0.4 mmol of benzonitrile, and 0.4 mmol of potassium hydroxide were added to a 10 mL reaction tube. 2 mL of toluene was added under air atmosphere, and the mixture was stirred in a heater at 150 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, centrifuged, and the supernatant was used to determine the conversion and selectivity using gas chromatography. The final calculated yield of the product was 41.8%. The filtered reaction solution was purified by thin-layer chromatography using petroleum ether and ethyl acetate as developing solvents to obtain the product. The characterization data of the product are as follows:

[0052] N-benzyl-4-chlorobenzamide: 1 H NMR (400MHz, CDCl3) δ7.83–7.75(m,2H),7.51(t,J=7.4Hz,1H),7.43(t,J=7.5Hz,2H),7.30(d,J=5.3Hz,3H),6.53(s,1H),4.61(d,J=5.8Hz,2H).

[0053] The reaction structure is as follows:

[0054]

[0055] Example 5:

[0056] 10 mg of NC-700-4 catalyst, 0.2 mmol of m-bromobenzyl alcohol, 0.4 mmol of benzonitrile, and 0.4 mmol of potassium hydroxide were added to a 10 mL reaction tube. 2 mL of toluene was added under air atmosphere, and the mixture was stirred in a heater at 150 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, centrifuged, and the supernatant was used to determine the conversion and selectivity using gas chromatography. The final calculated yield of the product was 32.0%. The filtered reaction solution was purified by thin-layer chromatography using petroleum ether and ethyl acetate as developing solvents to obtain the product. The characterization data of the product are as follows:

[0057] N-benzyl-3-bromobenzamide: 1 H NMR (400MHz, CDCl3) δ7.84–7.74(m,3H),7.50(dd,J=14.1,6.7Hz,2H),7.46–7.37(m,2H),7.20(t,J=7.7Hz,1H),6.68(s,1H),4.60(d,J=5.9Hz,2H).

[0058] The reaction structure is as follows:

[0059]

[0060] Example 6:

[0061] 10 mg of NC-700-4 catalyst, 0.2 mmol of 2-naphthalenemethanol, 0.4 mmol of benzonitrile, and 0.4 mmol of potassium hydroxide were added to a 10 mL reaction tube. 2 mL of toluene was added under air atmosphere, and the mixture was stirred in a heater at 150 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, centrifuged, and the supernatant was used for gas chromatography to determine the conversion and selectivity. The final calculated yield of the product was 86.0%. The filtered reaction solution was purified by thin-layer chromatography using petroleum ether and ethyl acetate as developing solvents to obtain the product. The characterization data of the product are as follows:

[0062] N-benzyl-2-naphthamide: 1 H NMR (400MHz, CDCl3) δ7.88–7.78(m,5H),7.56–7.40(m,6H),6.50(s,1H),4.82(d,J=5.6Hz,3H).

[0063] The reaction structure is as follows:

[0064]

[0065] Example 7:

[0066] 10 mg of NC-700-4 catalyst, 0.2 mmol of 2-thiophene methanol, 0.4 mmol of benzonitrile, and 0.4 mmol of potassium hydroxide were added to a 10 mL reaction tube. 2 mL of toluene was added under air atmosphere, and the mixture was stirred in a heater at 150 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, centrifuged, and the supernatant was used to determine the conversion and selectivity using gas chromatography. The final calculated yield of the product was 74.2%. The filtered reaction solution was purified by thin-layer chromatography using petroleum ether and ethyl acetate as developing solvents to obtain the product. The characterization data of the product are as follows:

[0067] N-benzylthiophene-2-carboxamide: 1 H NMR (400MHz, CDCl3)

[0068] The reaction structure is as follows:

[0069]

[0070] Example 8:

[0071] 10 mg of NC-700-4 catalyst, 0.2 mmol of benzyl alcohol, 0.4 mmol of p-methoxybenzonitrile, and 0.4 mmol of potassium hydroxide were added to a 10 mL reaction tube. 2 mL of toluene was added under air atmosphere, and the mixture was stirred in a heater at 150 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, centrifuged, and the supernatant was used to determine the conversion and selectivity using gas chromatography. The final calculated yield of the product was 58.2%. The filtered reaction solution was purified by thin-layer chromatography using petroleum ether and ethyl acetate as developing solvents to obtain the product. The characterization data of the product are as follows:

[0072] N-(4-methoxybenzyl)benzamide: 1 H NMR (400MHz, CDCl3) δ7.81–7.72(m,2H),7.39–7.26(m,5H),6.96–6.87(m,2H),6.37(s,1H),4.64(d,J=5.6Hz,2H),3.84(s,3H).

[0073] The reaction structure is as follows:

[0074]

[0075] Example 9:

[0076] 10 mg of NC-700-4 catalyst, 0.2 mmol of benzyl alcohol, 0.4 mmol of 2-furanocyanate, and 0.4 mmol of potassium hydroxide were added to a 10 mL reaction tube. 2 mL of toluene was added under air atmosphere, and the mixture was stirred in a heater at 150 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, centrifuged, and the supernatant was used to determine the conversion and selectivity using gas chromatography. The final calculated yield of the product was 38.7%. The filtered reaction solution was purified by thin-layer chromatography using petroleum ether and ethyl acetate as developing solvents to obtain the product. The characterization data of the product are as follows:

[0077] N-(thiophen-2-methyl)benzamide: 1 H NMR (400MHz, CDCl3) δ7.42 (ddd, J=

[0078] 13.4,4.3,1.1Hz,3H),7.29(s,2H),7.24(dd,J=4.9,3.6Hz,1H),7.19(s,0H),7.00(dd,J=5.0,3.7Hz,1H),6.25(s,1H),4.55(d,J=5.7Hz,3H).

[0079] The reaction structure is as follows:

[0080]

[0081] Example a:

[0082] 10 mg of NC-500-4 catalyst, 0.2 mmol of benzyl alcohol, 0.4 mmol of benzonitrile, and 0.4 mmol of potassium hydroxide were added to a 10 mL reaction tube. 2 mL of toluene was then added under air atmosphere, and the mixture was stirred in a heater at 150 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, centrifuged, and the supernatant was used to determine the conversion and selectivity using gas chromatography. The final calculated yield of the product was 47.9%.

[0083] The reaction structure is as follows:

[0084]

[0085] Example b:

[0086] 10 mg of NC-600-4 catalyst, 0.2 mmol of benzyl alcohol, 0.4 mmol of benzonitrile, and 0.4 mmol of potassium hydroxide were added to a 10 mL reaction tube. 2 mL of toluene was then added under air atmosphere, and the mixture was stirred in a heater at 150 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, centrifuged, and the supernatant was used to determine the conversion and selectivity using gas chromatography. The final calculated yield of the product was 62.1%.

[0087] The reaction structure is as follows:

[0088]

[0089] Example c:

[0090] 10 mg of NC-700-4 catalyst, 0.2 mmol of benzyl alcohol, 0.4 mmol of benzonitrile, and 0.4 mmol of potassium hydroxide were added to a 10 mL reaction tube. 2 mL of toluene was then added under air atmosphere, and the mixture was stirred in a heater at 140 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, centrifuged, and the supernatant was used to determine the conversion and selectivity using gas chromatography. The final calculated yield of the product was 33%.

[0091] The reaction structure is as follows:

[0092]

[0093] Example d:

[0094] 10 mg of NC-700-4 catalyst, 0.2 mmol of benzyl alcohol, 0.4 mmol of benzonitrile, and 0.4 mmol of sodium hydroxide were added to a 10 mL reaction tube. 2 mL of toluene was then added under air atmosphere, and the mixture was stirred in a 150 °C heater for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, centrifuged, and the supernatant was used to determine the conversion and selectivity of the reaction. It was found that the addition of sodium hydroxide did not produce the target product.

[0095] The reaction structure is as follows:

[0096]

[0097] Example e:

[0098] 10 mg of NC-700-4 catalyst, 0.2 mmol of benzyl alcohol, 0.4 mmol of benzonitrile, and 0.4 mmol of potassium carbonate were added to a 10 mL reaction tube. 2 mL of toluene was then added under air atmosphere, and the mixture was stirred in a 150 °C heater for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, centrifuged, and the supernatant was used to determine the conversion and selectivity of the reaction. It was found that the addition of potassium carbonate did not produce the target product.

[0099] The reaction structure is as follows:

[0100]

[0101] Example f:

[0102] 10 mg of NC-700-4 catalyst, 0.2 mmol of benzyl alcohol, 0.4 mmol of benzonitrile, and 0.4 mmol of potassium hydroxide were added to a 10 mL reaction tube. 2 mL of toluene was then added under air atmosphere, and the mixture was stirred in a heater at 150 °C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, centrifuged, and the supernatant was used to determine the conversion and selectivity using gas chromatography. The final calculated yield of the product was 47.0%.

[0103] The reaction structure is as follows:

[0104]

[0105] Example g:

[0106] 10 mg of NC-700-4 catalyst, 0.2 mmol of benzyl alcohol, 0.4 mmol of benzonitrile, and 0.4 mmol of potassium hydroxide were added to a 10 mL reaction tube. 2 mL of toluene was then added under air atmosphere, and the mixture was stirred in a heater at 150 °C for 4 hours. After the reaction was complete, the mixture was cooled to room temperature, centrifuged, and the supernatant was used to determine the conversion and selectivity using gas chromatography. The final calculated yield of the product was 85.0%.

[0107] The reaction structure is as follows:

[0108]

[0109] Example h:

[0110] 10 mg of NC-700-2 catalyst, 0.2 mmol of benzyl alcohol, 0.4 mmol of benzonitrile, and 0.4 mmol of potassium hydroxide were added to a 10 mL reaction tube. 2 mL of toluene was then added under air atmosphere, and the mixture was stirred in a heater at 150 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, centrifuged, and the supernatant was used to determine the conversion and selectivity using gas chromatography. The final calculated yield of the product was 73.5%.

[0111] The reaction structure is as follows:

[0112]

[0113] Example i:

[0114] 10 mg of NC-700-6 catalyst, 0.2 mmol of benzyl alcohol, 0.4 mmol of benzonitrile, and 0.4 mmol of potassium hydroxide were added to a 10 mL reaction tube. 2 mL of toluene was then added under air atmosphere, and the mixture was stirred in a heater at 150 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, centrifuged, and the supernatant was used to determine the conversion and selectivity using gas chromatography. The final calculated yield of the product was 58.6%.

[0115] The reaction structure is as follows:

[0116]

[0117] Table 2: Yields of target products under different reaction conditions

[0118]

[0119]

[0120] Reaction conditions: 0.2 mmol benzyl alcohol, 0.4 mmol benzonitrile, 0.4 mmol base, 2 mL toluene, 10 mg catalyst.

Claims

1. A method for synthesizing N-alkylamide compounds from alcohols and nitriles using nitrogen-carbon materials as catalysts, characterized in that: Alcohol compound 1, nitrile compound 2, potassium hydroxide, mesoporous nitrogen-carbon catalyst, and organic solvent were added to the reaction equipment and reacted in a heater at 140°C or above for more than 2 hours under stirring. After the reaction was completed, the mixture was centrifuged, filtered, and the supernatant was collected, separated and purified to obtain N-alkylated amide compound 3. ； 1 2 3； Ar1 and Ar2 are each independently selected from any one of aryl, heteroaryl, substituted aryl, and substituted heteroaryl; the aryl is selected from at least one of phenyl and naphthyl; the heteroaryl is selected from at least one of pyrrole, furanyl, thiophene, pyrazolyl, and imidazolyl; the substituents in the substituted aryl and substituted heteroaryl are each independently selected from at least one of methyl, methoxy, chlorine, and bromine; The molar ratio of alcohols to nitriles is 1:2; the molar ratio of alcohols to potassium hydroxide is 1:2; the amount of alcohol used in toluene is 0.1 mmol / mL. The preparation method of mesoporous nitrogen-carbon catalyst is as follows: o-phenylenediamine is dissolved in ethanol and distilled water, dilute nitric acid solution is added to adjust the pH to 2~6, then silica sol is added while stirring, hydrogen peroxide is added dropwise after stirring, stirred at room temperature, and dried to a solid material; The solid material was pyrolyzed in nitrogen at 500~700℃ for two hours. The prepared material was then treated with a 10wt% HF solution at room temperature to remove silica. After washing until neutral, the material was dried. The final product of nitrogen-doped carbon was denoted as NC-T-pH, where T is the pyrolysis temperature and pH represents the adjusted pH value.

2. The method for synthesizing N-alkylamide compounds from alcohols and nitriles catalyzed by the nitrogen-carbon material according to claim 1, characterized in that: The pyrolysis temperature is 700℃ and the pH value is 4.

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