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Preparation method of alpha-arylamidine imine derivative

A technology for aryl amidine imines and derivatives, which is applied in the field of preparation of α aryl amidine imine derivatives, can solve problems such as low yield and complex process, achieve high yield, improve reaction efficiency, and facilitate industrial application foreground effect

Active Publication Date: 2018-06-05
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to provide a kind of preparation method of α aryl amidine imine derivatives in order to solve technical problems such as complex process, low yield etc. The preparation method has the characteristics of simple preparation process and high yield, and does not require precious metals to generate intramolecular SP 3 Hybridization, and the post-processing is simple, with good prospects for industrial application

Method used

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  • Preparation method of alpha-arylamidine imine derivative
  • Preparation method of alpha-arylamidine imine derivative
  • Preparation method of alpha-arylamidine imine derivative

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Embodiment 1

[0033] A kind of preparation method of α aryl amidine imine derivative, its preparation process specifically comprises the following steps:

[0034] (1), add the cuprous catalyst of magnetic stirring bar and 0.075mmol (10.5mg) and the N-R1 of 0.5mmol (146mg) in 10ml sealing tube, the benzene sulfonamide that R2 replaces, nitrogen replacement 3-5 times, then Inject 1.5mmol (152mg) of R3-substituted terminal alkynes and 1.5mmol (296mg) of R4-substituted sulfonyl azide with a 100ul microsyringe, and inject 2ml of organic solvent dichloromethane into it with a 2.5ml syringe under nitrogen protection , and then add 1mmol (140μL) additive dropwise under the condition of stirring with a magnetic stirrer to control the dropping rate at 1ml / min. After the dropwise addition, seal the tube tightly and then control the temperature at 60°C for 12h to obtain the reaction solution , the reaction process was followed by thin-layer chromatography;

[0035] Described cuprous catalyst is CuBr; ...

Embodiment 2

[0050] A kind of preparation method of α aryl amidine imine derivative, its preparation process specifically comprises the following steps:

[0051] (1), add the cuprous catalyst of magnetic stirring bar and 0.05mmol (7mg) and the N-R1 of 0.5mmol (146mg) in 10ml sealed tube, the benzenesulfonamide substituted by R2, nitrogen replacement 3-5 times, then use Inject 0.5mmol (63mg) of R3-substituted terminal alkyne and 0.5mmol (99mg) R4-substituted sulfonyl azide into a 100ul microsyringe, and inject 2ml of organic solvent dichloromethane into it with a 2.5ml syringe under nitrogen protection. Then add 1 mmol (140 μL) additive dropwise under the condition of stirring with a magnetic stirrer to control the dropping rate at 1 ml / min. After the dropwise addition, seal the tube and tighten it, and then control the temperature at 60° C. to react for 12 hours to obtain a reaction solution. The progress of the reaction was followed by thin layer chromatography;

[0052] Described cuprou...

Embodiment 3

[0067] A kind of preparation method of α aryl amidine imine derivative, its preparation process specifically comprises the following steps:

[0068] (1), add the cuprous catalyst of magnetic stirring bar and 0.075mmol (10.5mg) and the N-R1 of 0.5mmol (146mg) in 10ml sealed tube, the benzenesulfonamide substituted by R2, nitrogen replacement 3-5 times, then Inject 1.5mmol (190mg) of R3-substituted terminal alkyne and 1.5mmol (296mg) R4-substituted sulfonyl azide with a 100ul microsyringe needle, and inject 2ml of organic solvent dichloromethane into it with a 2.5ml syringe under nitrogen protection , and then add 1mmol (140μL) additive dropwise under the condition of stirring with a magnetic stirrer to control the dropping rate at 1ml / min. After the dropwise addition, seal the tube tightly, and then control the temperature at 25°C for 12 hours to obtain a reaction solution , the reaction process was followed by thin-layer chromatography;

[0069] Described cuprous catalyst is ...

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Abstract

The invention discloses a preparation method of an alpha-arylamidine imine derivative. The preparation method comprises the steps of with N-R1,R2 substituted benzsulfamide, R3 substituted terminal alkyne and R4 substituted sulfonyl nitrine as the raw materials, reacting at a controlled temperature of 25-60 DEG C for 4-12 hours in an organic solvent, namely dichloromethane under the nitrogen protection by taking a metal cuprous catalyst in the presence of an additive, sequentially carrying out filtration, concentration and rotary evaporation on obtained reaction liquid, and carrying out columnchromatography separation under a condition that the volume ratio of petroleum ether to acetic acid in eluant is 3 to 1, so as to obtain a product, namely the alpha-arylamidine imine derivative. According to the preparation method, the alpha-arylamidine imine derivative is prepared by virtue of a ''one-pot method'', the maximum yield of the product can reach 95%, meanwhile, the reaction efficiencyis improved, and the post-treatment is simple; and the preparation method has relatively wide industrial application prospects.

Description

technical field [0001] The invention relates to a preparation method of α-arylamidine derivatives, which belongs to the field of organic chemistry. Background technique [0002] α-aryl amidine imine derivatives belong to amines, which widely exist in the biological world and have extremely important physiological and biological activities. Since its amine-based compounds have very broad application prospects, research on more effective preparation methods has attracted great attention from researchers. At present, the reports on amine-based compounds all use a multi-step method, using amine groups with or without protective groups to react to obtain the corresponding products, and then remove the protective groups to obtain reaction intermediates and final products. This method requires at least two steps of reaction, the process is cumbersome and the yield is low. [0003] In summary, the current preparation methods of α-arylamidine derivatives have technical problems suc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/36C07C303/40C07C303/44C07C311/49
CPCC07C303/36C07C303/40C07C303/44C07C311/49
Inventor 易封萍黄颖樊彦霞孙启辉易维银张丽荣
Owner SHANGHAI INST OF TECH
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