Benzoin oxime derivative and preparation method thereof

A technology of benzoin oxime and its derivatives, which is applied in the field of benzoin oxime derivatives and its preparation, can solve problems such as inconvenient use, threats to human body and environmental safety, etc., and achieve the effects of complex and diverse structures and broad application prospects

Active Publication Date: 2015-03-25
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] With sodium cyanide and potassium cyanide as catalysts, benzaldehyde molecules condense to generate benzoin, and then use benzoin to react with hydroxylamine hydrochloride under the action of alkali anhydrous potassium carbonate to prepare benzoin oxime, but sodium cyanide and potassium cyanide are highly toxic. Poisons pose a huge threat to the safety of the human body and the environment, and are inconvenient to use

Method used

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  • Benzoin oxime derivative and preparation method thereof
  • Benzoin oxime derivative and preparation method thereof
  • Benzoin oxime derivative and preparation method thereof

Examples

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Effect test

Embodiment 1

[0033] A benzoin oxime derivative, the structural formula is:

[0034]

[0035] A kind of preparation method of benzoin oxime derivative, described preparation method comprises the following steps:

[0036] a. Precursor synthesis;

[0037] b. Synthesis of the target product;

[0038] c. Purification.

[0039] Wherein, a, precursor synthesis, comprises the following steps:

[0040] (1) With 830mmol sodium hydride as a catalyst, 200mmol diethyl malonate and 440mmol propargyl bromide were added to 250mL anhydrous acetonitrile in an ice-water bath, stirred and reacted for 8 hours, the product was washed with water, extracted with ethyl acetate, and Press and spin dry, column chromatography (volume ratio ethyl acetate:petroleum ether=1:100) to obtain a white solid product, namely compound 1;

[0041] (2) Mix 80mmol of compound 1 with 200mmol of phenylethynyl bromide in 1.3g of Pd (PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system, Pd(PPh 3 ) 2 Cl 2 The mol...

Embodiment 2

[0053] A benzoin oxime derivative, the structural formula is:

[0054]

[0055] A kind of preparation method of benzoin oxime derivative, described preparation method comprises the following steps:

[0056] a. Precursor synthesis;

[0057] b. Synthesis of the target product;

[0058] c. Purification.

[0059] Wherein, a, precursor synthesis, comprises the following steps:

[0060] (1) With 800mmol sodium hydride as a catalyst, 200mmol diisopropyl malonate and 500mmol propargyl bromide were added to 200ml anhydrous acetonitrile in an ice-water bath, stirred and reacted for 10 hours, the product was washed with water, extracted with ethyl acetate, Spinning to dryness under reduced pressure, column chromatography (volume ratio of ethyl acetate:petroleum ether=1:100) gave a white solid product, namely compound 3;

[0061] (2) Mix 80mmol compound 1 with 200mmol p-methylphenylethynyl bromide in 2.17gPd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system, Pd(PPh 3...

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Abstract

The invention relates to a benzoin oxime derivative and a preparation method thereof. A structural formula of the benzoin oxime derivative is shown in the specification. The preparation method comprises the following steps: reacting malonate with propargyl bromide in anhydrous acetonitrile under the catalysis of sodium hydride to obtain a white solid product; by taking triethylamine as alkali, reacting the white solid product with phenylethynyl bromine or substituted phenylethynyl bromine in anhydrous acetonitrile under the catalysis of Pd(PPh3)2Cl2/CuI to obtain a light brown solid product; reacting the light brown solid product with benzoin oxime in toluene at 95-105 DEG C to obtain the benzoin oxime derivative. A brand new synthetic method of polysubstituted benzoin oxime is provided, and a series of new benzoin oxime derivatives are generated. Compared with normal benzoin oxime derivatives, the benzoin oxime derivative prepared by virtue of the preparation method has relatively complex and diverse structures by virtue of multiple cycles, and presents relatively wide application prospects in chemical industry production and clinic medicines.

Description

technical field [0001] The invention relates to the field of organic compounds, in particular to a benzoin oxime derivative and a preparation method thereof. Background technique [0002] Benzoin, benzoin oxime and their derivatives are widely used in industrial production and scientific research. For example, benzoin, benzoin oxime and their derivatives are important intermediates in organic synthesis and fine chemicals, and are widely used in chemical industry, medicine, spices, chelating agents, coatings and other fields. In view of the special importance of benzoin, benzoin oxime and their derivatives, how to expand the synthetic route of benzoin oxime and its derivatives has aroused countless organic synthesizers and chemists to actively think, and came up with some very effective methods. [0003] The common synthetic methods of benzoin and benzoin oxime are: [0004] 1. Using sodium cyanide and potassium cyanide as catalysts: [0005] With sodium cyanide and potass...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/24C07C249/02
Inventor 胡益民潘相相
Owner ANHUI NORMAL UNIV
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