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Preparation method of 2, 5-dimethoxy-beta-nitrostyrolene

A technology of nitrostyrene and dimethoxybenzaldehyde, applied in the field of medicinal chemistry, can solve the problems of unrealistic industrial production, expensive raw materials, and low target yield, and achieve low toxicity, good removal effect, and stable process Effect

Pending Publication Date: 2022-05-06
HANGZHOU QIANTAI BIOLOGICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current synthetic methods all have unsatisfactory factors such as expensive raw materials and low target yields, which cannot realize industrial production and can only be used for scientific research and experiments.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] The method for preparing 2,5-dimethoxy-B-nitrostyrene comprises the following steps:

[0018] Step (1) Put 83kg of 2,5-dimethoxybenzaldehyde, 350L of ethyl acetate, 61kg of nitromethane, and 23kg of ammonium acetate into the reaction kettle, raise the temperature to 75-78°C under stirring, and react for 4 hours.

[0019] Ensure that the mass ratio of each material in the reaction system is: 2,5-dimethoxybenzaldehyde:nitromethane:ethyl acetate:ammonium acetate=1:0.73:4.2:0.27.

[0020] Step (2) Add 500 L of hot water to the above reaction solution, stir and wash for half an hour, stand still, and separate layers. The water layer can be applied to the next batch. The organic layer was directly cooled and centrifuged to obtain the finished product of 2,5-dimethoxy-B-nitrostyrene.

[0021] In step (2), the stratified water layer can be directly applied to the next batch of step 2. After being applied mechanically to saturation, desalination is carried out by distillation...

Embodiment 2

[0024] The method for preparing 2,5-dimethoxy-B-nitrostyrene comprises the following steps:

[0025] (1) Put 83kg of 2,5-dimethoxybenzaldehyde, 415L of toluene, 61kg of nitromethane, and 25kg of ammonium acetate into the reaction kettle, heat up to 75-78°C under stirring, and react for 4 hours.

[0026] Ensure that the mass ratio of each material in the reaction system is: 2,5-dimethoxybenzaldehyde:nitromethane:toluene:ammonium acetate=1:0.73:5:0.3.

[0027] (2) Add 500 L of hot water to the above reaction solution, stir and wash for half an hour, stand still, and separate layers. The water layer can be applied to the next batch. The organic layer was directly cooled and centrifuged to obtain the finished product of 2,5-dimethoxy-B-nitrostyrene.

[0028] In step (2), the stratified water layer can be directly applied to the next batch of step 2. After being applied mechanically to saturation, desalination is carried out by distillation, and the water obtained can be applied...

Embodiment 3

[0031] The method for preparing 2,5-dimethoxy-B-nitrostyrene comprises the following steps:

[0032] (1) Put 83kg of 2,5-dimethoxybenzaldehyde, 400L of xylene, 61kg of nitromethane, and 25kg of ammonium acetate into the reaction kettle, raise the temperature to 75-78°C under stirring, and react for 4 hours.

[0033] Ensure that the mass ratio of each material in the reaction system is: 2,5-dimethoxybenzaldehyde:nitromethane:xylene:ammonium acetate=1:0.73:4.8:0.3.

[0034] (2) Add 500 L of hot water to the above reaction solution, stir and wash for half an hour, stand still, and separate layers. The water layer can be applied to the next batch. The organic layer was directly cooled and centrifuged to obtain the finished product of 2,5-dimethoxy-B-nitrostyrene.

[0035] In step (2), the stratified water layer can be directly applied to the next batch of step 2. After being applied mechanically to saturation, desalination is carried out by distillation, and the water obtained ...

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PUM

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Abstract

The invention discloses a preparation method of 2, 5-dimethoxy-beta-nitrostyrolene, which comprises the following steps: step (1), adding materials of 2, 5-dimethoxybenzaldehyde, nitromethane, ammonium acetate and an organic solvent into a reaction kettle according to the mass ratio of 2, 5-dimethoxybenzaldehyde to nitromethane to the organic solvent to ammonium acetate of 1: (0.7-0.9): (4-5): (0.25-0.3), reacting for 1-2 hours, and cooling to room temperature to obtain 2, 5-dimethoxy-beta-nitrostyrolene; reacting for 4 to 10 hours at the temperature of 70 to 80 DEG C; (2) adding an aqueous solution into the reaction liquid in the step (1), washing, and separating into a water layer and an organic layer; and directly cooling and crystallizing the organic layer, and centrifuging to obtain a 2, 5-dimethoxy-beta-nitrostyrolene finished product. The reaction organic solvent and the aqueous solution for washing can be recycled, the removal effect on byproducts is good, resources are saved, and the cost is reduced. Clean production is realized, and no three wastes are generated; the method is high in raw material conversion rate, stable in process and suitable for industrial production.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a preparation method of 2,5-dimethoxy-β-nitrostyrene. Background technique [0002] β-nitrostyrene compounds are widely used in the fields of medicine, agriculture, production development, etc., especially in the medical field, β-nitrostyrene compounds can be used as active ingredients of AIDS drugs. [0003] There are currently some methods that use aromatic aldehydes and nitroalkanes to perform Henry reaction under alkaline conditions, and then condense to generate β-nitrostyrene. This reaction has many side reactions, and the product itself has a fast polymerization speed and is difficult to separate. Very difficult, resulting in a relatively low yield of the target product. There are also some β-nitrostyrenes prepared from alkenes, which use organoselenium to convert inactive alkenes into nitroalkenes. However, the current synthetic methods all have unsatisfactory factors...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/32
CPCC07C201/12C07C205/32
Inventor 李先泰
Owner HANGZHOU QIANTAI BIOLOGICAL TECH
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