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A method for continuous flow synthesis of α-ketoamides using microflow field technology

A technology of flow synthesis and micro-flow field, which is applied in the preparation of carboxylic acid amide, chemical instruments and methods, and the preparation of organic compounds, etc. It can solve the problems of unavoidable side reactions, cumbersome reaction steps, and difficult operation, so as to avoid side reactions , shorten the reaction time, the effect of short contact time

Active Publication Date: 2019-02-26
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved in the present invention is to provide a method for continuous flow synthesis of α-ketoamides using micro-flow field technology to solve the existing technical problems of cumbersome reaction steps, difficult operation, long time-consuming, low yield, and side reactions. unavoidable

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  • A method for continuous flow synthesis of α-ketoamides using microflow field technology
  • A method for continuous flow synthesis of α-ketoamides using microflow field technology
  • A method for continuous flow synthesis of α-ketoamides using microflow field technology

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Effect test

Embodiment 1

[0026] Weigh 2.82g, 0.02mol specification of 2,2,6,6,-tetramethylpiperidine oxide fully dissolved in 50ml of toluene solvent, then weigh 12.21g, 0.1mol specification of α-methylbenzyl alcohol, 11.81 g, 0.1 mol of p-aminobenzonitrile, 15.82 g, 0.2 mol of pyridine in the above solvent, add toluene solvent to make the total volume to 200 ml. Add 1.62 g, 0.01 mol ferric chloride powder to the above fixed liquid, and stir it into a uniform heterogeneous state with a stirrer. Feed nitrogen back pressure to the Corning reactor to 10bar, switch to oxygen, and pump the heterogeneous solution into the reactor at the same time. Keep the reaction temperature at 80°C, the heterogeneous solution flow rate is 10ml / min, the gas flow rate is 0.5L / min, and the reaction time is about 1.1min, that is, 1.1min after the reaction starts, the reaction solution is collected in the collection bottle. According to high-performance liquid chromatography analysis, in this reaction, the conversion rate of...

Embodiment 2

[0028] Weigh 2.82g, 0.02mol specification of 2,2,6,6,-tetramethylpiperidine oxide fully dissolved in 50ml of toluene solvent, then weigh 12.21g, 0.1mol specification of α-methylbenzyl alcohol, 23.62g, 0.2mol of p-aminobenzonitrile, 15.82g, 0.2mol of pyridine in the above solvent, and add toluene solvent to make the total volume to 200ml. Add 1.62 g, 0.01 mol ferric chloride powder to the above fixed liquid, and stir it into a uniform heterogeneous state with a stirrer. Feed nitrogen back pressure to the Corning reactor to 10bar, switch to oxygen, and pump the heterogeneous solution into the reactor at the same time. Keep the reaction temperature at 80°C, the heterogeneous solution flow rate is 10ml / min, the gas flow rate is 0.5L / min, and the reaction time is about 1.1min, that is, 1.1min after the reaction starts, the reaction solution is collected in the collection bottle. Through high-performance liquid chromatography analysis, in this reaction, the conversion rate of the α...

Embodiment 3

[0030] Weigh 2.82g, 0.02mol specification of 2,2,6,6,-tetramethylpiperidine oxide fully dissolved in 50ml of toluene solvent, then weigh 12.21g, 0.1mol specification of α-methylbenzyl alcohol, 35.44 g, 0.3 mol of p-aminobenzonitrile, 15.82 g, 0.2 mol of pyridine in the above solvent, and add toluene solvent to make the total volume to 200 ml. Add 1.62 g, 0.01 mol ferric chloride powder to the above fixed liquid, and stir it into a uniform heterogeneous state with a stirrer. Feed nitrogen back pressure to the Corning reactor to 10bar, switch to oxygen, and pump the heterogeneous solution into the reactor at the same time. Keep the reaction temperature at 80°C, the heterogeneous solution flow rate is 10ml / min, the gas flow rate is 0.5L / min, and the reaction time is about 1.1min, that is, 1.1min after the reaction starts, the reaction solution is collected in the collection bottle. According to high-performance liquid chromatography analysis, in this reaction, the conversion rat...

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Abstract

The invention discloses a method used for synthesizing alpha-ketoamides via micro flow field technology continuous flow. The method comprises following steps: 1, alpha-methylbenzyl alcohol, an amine compound, an acid binding agent, a catalyst, 2,2,6,6-tetramethylpiperidinooxy, and a benzene series solvent are mixed at a certain ratio so as to obtain a heterogeneous solution; 2, the heterogeneous solution and oxygen are pumped into a microreactor for reaction with stirring of the heterogeneous solution, after reaction an effluent is collected, and alpha-ketoamides is obtained via processing. The microreactor is high in specific surface area, heat transfer and mass transfer capability is high, and safety is high; reaction volume is small, reaction duration time is short, reaction is rapid, and yield is high; the method is capable of realizing continuous production; equipment and energy loss is low, and industrial application prospect is promising.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a continuous-flow method for synthesizing alpha-ketoamides using micro-flow field technology. Background technique [0002] α-Ketoamide is the core skeleton structure of many drugs and natural products, and plays an important role in organic synthesis, drug synthesis, biochemistry, polymer materials, and natural products. In terms of organic synthesis, α-ketoamides can be transformed into α-amino acids, β-lactams, α-hydroxy acids, and heterocyclic compounds. The amide bond is one of the most basic functional groups in the field of medicine. According to statistics, about a quarter of the drugs contain amide bonds, so α-ketoamides are of great significance in biomedicine. In the field of biochemistry, the amide bond is usually represented as the key structural unit of the peptide bond in the protein molecule, which is derived from the dehydration reaction o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C253/30C07C255/60C07C231/14C07C235/78C07C231/12C07C237/42B01J19/00
CPCB01J19/0093C07C231/12C07C231/14C07C253/30C07C255/60C07C235/78C07C237/42
Inventor 郭凯曾雨方正刘成扣欧阳平凯
Owner NANJING TECH UNIV