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Green synthesis method for schiff base compounds

A synthesis method and compound technology, which are applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., can solve the problems of cumbersome operation, large amount of catalyst, difficult to reuse, etc. To achieve the effect of simple reaction operation

Active Publication Date: 2013-11-13
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In order to solve a series of problems in the prior art for the preparation of Schiff base compounds, such as large amount of catalyst used, difficult to reuse, cumbersome operation, etc., and follow a greener and more efficient synthesis concept, the present invention provides a carboxylated The acid-type acidic ionic liquid is a method for synthesizing Schiff base compounds as a catalyst. The method is easy to operate, the product yield is high and easy to separate, and the carboxylic acid-type acidic ionic liquid can be directly reused many times.

Method used

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  • Green synthesis method for schiff base compounds
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  • Green synthesis method for schiff base compounds

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Embodiment 1

[0023] Carboxylic acid type acidic ionic liquid 1-carboxymethyl-3-methylimidazole hydrochloride (9mg, 0.05mmol) was added in a 50ml double-necked round bottom flask containing cyclohexanone (20ml), then aniline (0.48g , 5mmol) into the reaction vessel, under mechanical stirring, the oil bath heating and reflux water separation reaction 10h, cooled to room temperature, poured out the reaction solution, obtained Schiff base N-cyclohexyliminoaniline 0.85g after precipitation, Yield 98%, product structural formula is:

[0024]

Embodiment 2

[0026] Carboxylic acid-type acidic ionic liquid 1-carboxymethyl-3-butylimidazolium tetrafluoroborate (14mg, 0.05mmol) was added to a 50ml double-necked round bottom flask filled with 3-methyl-2-butanone (20ml) Add p-methylaniline (0.54g, 5mmol) to the reaction vessel again, under mechanical stirring, heat the oil bath to reflux and divide water for 10h, cool to room temperature, pour out the reaction solution, and obtain the Schiff base after precipitation N-(3-methyl-2-butylimino)-4-methylaniline 0.86g, yield 98%, product structural formula is:

[0027]

Embodiment 3

[0029] Carboxylic acid-type acidic ionic liquid 1-(4-carboxybutyl)-3-methylimidazolium p-toluenesulfonate (17mg, 0.05mmol) was added to a 50ml double-necked round bottom flask filled with 3-pentanone (20ml) , then added 3,4-dimethylaniline (0.61g, 5mmol) to the reaction vessel, under mechanical stirring, the oil bath was heated to reflux for water separation for 10h, cooled to room temperature, and the reaction solution was poured out to obtain Schiff base N-(3-pentylimino)-3,4-dimethylaniline 0.90g, yield 95%, product structural formula is:

[0030]

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Abstract

The invention discloses a green synthesis method for schiff base compounds. The synthesis method comprises that ketone and aromatic amine are used as substrates and reacted under the catalysis of carboxylic acid type acidic ionic liquid to obtain the corresponding schiff base compounds. The operation is simple and convenient, the yield of the products is high, the products can be easily separated, and the carboxylic acid type acidic ionic liquid can be directly reused for many times.

Description

(1) Technical field [0001] The invention relates to a green method for synthesizing Schiff base compounds with ketones and aromatic amines as substrates. (2) Background technology [0002] Aldehydes or ketones and aromatic amines are dehydrated and condensed under acid catalysis to obtain imines, also known as Schiff bases. Schiff base compounds are important intermediates in organic synthesis, and are widely used in the fields of medicine, pesticides, spices, etc. Especially in recent years, Schiff bases are frequently used in the synthesis of various drugs. Ketones are less reactive than aldehydes, and they need to be condensed with aromatic amines to obtain Schiff bases under conditions such as high temperature reflux and water separation, and the yields are often very low. Adding acid can accelerate the departure of water in the reaction, which is an important method for catalyzing the synthesis of Schiff base compounds. The more commonly used acids are benzoic acid, p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/45C07C211/52C07C211/58C07C209/28C07D309/28B01J31/04
Inventor 罗书平许丹倩徐振元
Owner ZHEJIANG UNIV OF TECH