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Preparation method of O-benzylhydroxylamine hydrochloride

A technology of benzyloxyamine hydrochloride and dilute hydrochloric acid, applied in organic chemistry and other directions, can solve the problems of flammable and toxic environment pollution, raw material sodium hydride burning, increase waste water pollution and other problems, to improve atom utilization, The effect of reducing alkalinity and reducing the amount of waste water

Active Publication Date: 2019-07-02
ZHEJIANG SAINON CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Firstly, the formation of oxime sodium in the reaction mechanism is questionable, secondly, the raw material sodium hydride is easy to cause combustion and explosion, and the final reaction yield is not high
[0006] (2) Maskill, H (Maskill, H.J.Chem.Soc., Perkin Trans.2001, 2:1742-1747.) Starting from N-hydroxy phthalimide, using Mitsunobu reaction to generate N-benzyloxy substituted ortho Benzimide, using a more hindered group to protect the hydrogen on the nitrogen, so that the base only reacts with the hydrogen on the oxygen, the reaction operation is simple, and the use of hydrazine can be avoided, but the amount of by-products is large and difficult to handle
It is not difficult to see that this method has a long process route, complicated conditions, and many wastes.
[0008] (4) Patent CN102093253A discloses a preparation method of benzyloxyamine hydrochloride compounds, adding ketoxime, solvent, alkali metal hydroxide into the reaction vessel, adding chlorobenzyl compounds while stirring, the solvent is DMSO or ion Liquid [BMIM]Cl, [BMIM]OH, alkali metal hydroxide is sodium hydroxide or potassium hydroxide, but DMSO is flammable, toxic and polluting to the environment, ionic liquid [BMIM]Cl is acidic, [BMIM ]Cl will react with alkali metal hydroxides, and sodium hydroxide and potassium hydroxide will increase the pollution of wastewater produced by the reaction due to their strong alkalinity

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Add 47.5g (0.55mol) butanone oxime into a 500mL three-necked flask equipped with a constant pressure funnel and a stirring device. When the temperature rises to 30°C, slowly add 63.3g (0.5mol) of chlorine Benzyl and 128.8g (0.55mol) potassium methylate methanol solution (30% concentration) were added dropwise, and the dropwise addition was completed in about 1 hour. The reaction was stirred and reacted at 30°C for 6 hours, and the reaction system was detected and analyzed by chromatography until no benzyl chloride peak appeared, which was recorded as the product 1. After solid-liquid separation of the product 1, take the liquid phase and add 20% dilute hydrochloric acid to carry out hydrolysis and rectification. While adding dilute hydrochloric acid dropwise, butanone and methanol are separated by distillation, which is recorded as product 2. Concentrate the product 2 to separate benzyloxylamine hydrochloride; finally dry to obtain pure benzyloxylamine hydrochloride, th...

Embodiment 2

[0044] Add 47.5g (0.55mol) butanone oxime into a 500mL three-necked flask equipped with a constant pressure funnel and a stirring device. When the temperature rises to 30°C, slowly add 63.3g (0.5mol) of chlorine Benzyl and 154.3g (0.65mol) potassium methylate methanol solution (30% concentration) were added dropwise, and the dropwise addition was completed in about 1 hour. The reaction was stirred at 30°C for 6 hours, and the reaction system was detected and analyzed by chromatography until no benzyl chloride peak appeared, which was recorded as the product 1. After solid-liquid separation of the product 1, take the liquid phase and add 20% dilute hydrochloric acid to carry out hydrolysis and rectification. While adding dilute hydrochloric acid dropwise, butanone and methanol are separated by distillation, which is recorded as product 2. Concentrate the product 2 to separate benzyloxylamine hydrochloride; finally dry to obtain pure benzyloxylamine hydrochloride, the conversion...

Embodiment 3

[0046] Add 56.7g (0.65mol) butanone oxime into a 500mL three-neck flask equipped with a constant pressure funnel and a stirring device, and when the temperature rises to 30°C, slowly add 63.3g (0.5mol) of chlorine Benzyl and 128.8g (0.55mol) potassium methylate methanol solution (30% concentration) were added dropwise, and the dropwise addition was completed in about 1 hour. The reaction was stirred and reacted at 30°C for 6 hours, and the reaction system was detected and analyzed by chromatography until no benzyl chloride peak appeared, which was recorded as the product 1. After solid-liquid separation of the product 1, take the liquid phase and add 20% dilute hydrochloric acid to carry out hydrolysis and rectification. While adding dilute hydrochloric acid dropwise, butanone and methanol are separated by distillation, which is recorded as product 2. Concentrate the product 2 to separate benzyloxylamine hydrochloride; finally dry to obtain pure benzyloxylamine hydrochloride, ...

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PUM

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Abstract

The invention discloses a preparation method of O-benzylhydroxylamine hydrochloride, and relates to the technical field of organic synthesis. The method comprises the following steps: synchronously dropwise adding alcoholic solutions of benzyl halide and alkoxide into oxime to perform a reaction; when no benzyl halide exists in the reaction system, carrying out solid-liquid separation, dropwise adding dilute hydrochloric acid for carrying out hydrolytic rectification, and distilling while dropwise adding the dilute hydrochloric acid to separate out ketone; concentrating the reaction solution and separating out O-benzylhydroxylamine hydrochloride; and drying the benzylamine hydrochloride to obtain an O-benzylhydroxylamine hydrochloride pure product. Oxime is used as a raw material, and thefinally generated ketone or aldehyde can also be recycled to synthesize corresponding oxime. According to the method, the atom utilization rate is improved, the production cost of the product is reduced, the emission of three wastes is reduced, and the goal of green production is achieved.

Description

[0001] Technical field: [0002] The invention relates to the technical field of organic synthesis, in particular to a preparation method of benzyloxyamine hydrochloride. [0003] Background technique: [0004] Benzyloxyamine hydrochloride is an important intermediate in organic synthesis and pharmaceutical synthesis. When being applied to drug synthesis, the basic requirement to the purity of benzyloxyamine hydrochloride must be more than 98% (measured by potentiometric titration). The reported benzyloxylamine hydrochloride preparation method has following several: [0005] (1) Patent CN1488625A discloses a method for synthesizing benzyloxyamine hydrochloride, using DMF as a solvent, reacting sodium hydride and ketoxime to generate oxime sodium, then reacting with benzyl chloride to generate oxime benzyl ether, and finally hydrolyzing and concentrating to obtain benzyl Oxyamine hydrochloride. Firstly, the generation of sodium oxime in the reaction mechanism is questionable,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C239/20
CPCC07C239/20
Inventor 曹文兵
Owner ZHEJIANG SAINON CHEM
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