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Synthetic method for preparing amide compounds through co-catalysis of niobium pentachloride and ionic liquid

A technology of amide compounds and ionic liquids, which is applied in the preparation of organic compounds, organic compound/hydride/coordination complex catalysts, chemical instruments and methods, etc., can solve the problem of low economy of reaction atoms, complicated post-treatment, Low yield and other problems, to achieve the effect of reducing catalyst consumption, less catalyst consumption, and reducing production cost

Pending Publication Date: 2020-06-23
JILIN INST OF CHEM TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The object of the present invention is to provide a kind of synthetic method that niobium pentachloride and ionic liquid co-catalyze and prepare amide compounds, to solve the problem that amine and NbCl 5 The dosage is large, the reaction atom economy is not high, the post-processing is complicated, and the technical problems of low yield

Method used

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  • Synthetic method for preparing amide compounds through co-catalysis of niobium pentachloride and ionic liquid
  • Synthetic method for preparing amide compounds through co-catalysis of niobium pentachloride and ionic liquid
  • Synthetic method for preparing amide compounds through co-catalysis of niobium pentachloride and ionic liquid

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Experimental program
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Effect test

Embodiment 1

[0036]

[0037] Benzoic acid (244mg, 2mmol), niobium pentachloride (11mg, 0.08mmol), ionic liquid 5 (22mg, 0.05mmol) and 4A molecular sieves (122mg, 50%, w / w%) were added to a round bottom flask, followed by Add toluene (4 mL, 2 mL / mmol), stir at room temperature for 30 minutes, then add benzylamine (214 mg, 2 mmol), heat up to reflux, and react for 24 hours. After the reaction was complete, the column was subjected to flash column chromatography (petroleum ether→ethyl acetate:triethylamine (200:1, v / v) to obtain 405 mg of a white solid with a yield of 96%. 1 H NMR (400MHz, CDCl 3 )δ7.809(d, J=7.2Hz, 2H), 7.50(t, J=7.2Hz, 1H), 7.43(t, J=7.2Hz, 2H), 7.38–7.34(m, 4H), 7.33– 7.27(m, 1H), 6.42(br.s, 1H), 4.65(d, J=5.6Hz, 1H), see figure 1 .

[0038] Synthesis of Ionic Liquid 5

[0039]

[0040] Add N-methylimidazole (4.6 g, 0.05 mol) into a round bottom flask and preheat it to 70° C., slowly add bromobutane dropwise, and continue heating to reflux for 4 h. After the com...

Embodiment 2

[0042]

[0043] 2-Picolinic acid (246 mg, 2 mmol), niobium pentachloride (11 mg, 0.08 mmol), ionic liquid 5 (22 mg, 0.05 mmol) and 4A molecular sieves (122 mg, 50%, w / w%) were added to a round bottom flask , then added toluene (4mL, 2mL / mmol), stirred at room temperature for 30 minutes, then added benzylamine (214mg, 2mmol), raised the temperature to reflux, and reacted for 24 hours. After the reaction was complete, the column was subjected to flash column chromatography (petroleum ether→ethyl acetate:triethylamine (200:1, v / v) to obtain 365 mg of white solid with a yield of 86%. 1 H NMR (400MHz, CDCl 3 )δ8.94(d,J=1.9Hz,1H),8.66(dd,J=4.8,1.2Hz,1H),8.12(d,J=8.0Hz,1H),7.42–7.22(m,6H), 6.86(br.s, 1H), 4.63(d, J=5.7Hz, 2H), see figure 2 .

Embodiment 3

[0045]

[0046] Add 3-thiophenecarboxylic acid (256 mg, 2 mmol), niobium pentachloride (11 mg, 0.08 mmol), ionic liquid 5 (22 mg, 0.05 mmol) and 4A molecular sieves (122 mg, 50%, w / w%) into a round bottom flask , then added toluene (4mL, 2mL / mmol), stirred at room temperature for 30 minutes, then added benzylamine (214mg, 2mmol), raised the temperature to reflux, and reacted for 24 hours. After the reaction was complete, the column was subjected to flash column chromatography (petroleum ether→ethyl acetate:triethylamine (200:1, v / v) to obtain 386 mg of white solid with a yield of 89%. 1 H NMR (400MHz, CDCl 3 )δ7.90–7.83(m,1H),7.39(dd,J=4.8,0.8Hz,1H),7.35–7.25(m,6H),6.42(br.s,1H),4.59(d,J= 6.0Hz, 2H), NMR see image 3 .

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Abstract

The invention relates to a synthetic method for preparing amide compounds through co-catalysis of niobium pentachloride and ionic liquid. The preparation method is characterized by comprising the following steps: weighing organic carboxylic acid, organic amine, niobium pentachloride, ionic liquid and a molecular sieve, adding the materials into a reactor, adding an organic solvent, and reacting for 6-24 hours at the reaction temperature of 70-110 DEG C to obtain a corresponding amide product. The molar ratio of the organic carboxylic acid to the organic amine to the niobium pentachloride to the ionic liquid is 1:(1-3):(0.01-1):(0.05-1); wherein the mass ratio of the organic carboxylic acid to the molecular sieve is 1: (0.2-1). According to the method, the substrate range is expanded, the reaction yield is high (95% or above), the catalyst dosage is small, the atom economy is high, the catalyst is cheap and easy to obtain, the production cost can be greatly reduced, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a synthesis method of amide compounds, in particular to a synthesis method of co-catalyzing niobium pentachloride and ionic liquid to prepare amide compounds. Background technique [0002] Amides are one of the most common compounds among natural bioactive molecules and synthetic organic compounds. The synthesis of amides has important applications in medicinal chemistry, biochemistry and polymer synthesis. Studies have shown that more than a quarter of currently marketed drugs are amide compounds, such as atorvastatin, which can prevent cholesterol production, valsartan, an angiotensin receptor inhibitor, and diltiazem, which treats angina pectoris and high blood pressure. This makes the amidation reaction one of the most commonly used reactions in the pharmaceutical field. In addition, amide compounds are also widely used as chemical raw materials in the fields of lub...

Claims

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Application Information

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IPC IPC(8): C07C231/02C07C233/65C07D213/81C07D333/38C07D207/16C07D295/192C07C235/34C07C233/11B01J31/02B01J31/36
CPCC07C231/02C07D213/81C07D333/38C07D207/16C07D295/192B01J31/0281B01J31/36C07C233/65C07C235/34C07C233/11Y02P20/54
Inventor 于雪张跃伟包青青
Owner JILIN INST OF CHEM TECH
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