Method for synthesizing Schiff base compound containing camphenyl

A synthesis method and compound technology, which are applied in the field of synthesis of camphenyl-based Schiff base compounds, can solve the problems that there is no synthesis method for camphenyl-based Schiff base compounds, and achieve high yield, low secondary pollution, The effect of mild reaction conditions

Active Publication Date: 2016-01-20
JIANGXI AGRICULTURAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, still do not have the synthetic method of described camphenyl Schiff base compound

Method used

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  • Method for synthesizing Schiff base compound containing camphenyl
  • Method for synthesizing Schiff base compound containing camphenyl
  • Method for synthesizing Schiff base compound containing camphenyl

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preparation example Construction

[0019] A kind of synthetic method that contains camphenyl Schiff base compound is characterized in that, concrete synthetic steps are as follows:

[0020] (1) Using camphenal as raw material, add aromatic amine compounds in the reaction device with water separator, the aromatic amine is aniline or substituted aniline, and the substituted aniline is o-toluidine, p-toluidine, p-bromoaniline, ortho-toluidine One of chloroaniline, p-chloroaniline, p-methoxyaniline, m-nitroaniline, p-nitroaniline;

[0021] Camphenal and aromatic amine are fed in a molar ratio of 1:1 to 1.1, then organic solvent benzene or cyclohexane is added, stirred and refluxed for 2 to 3 hours, and the reaction progress is tracked by the gas phase until the content of the target product no longer increases;

[0022] (2) benzene or cyclohexane solvent in the above-mentioned reaction solution are steamed out, and the crude product obtained is purified with methanol or ethanol, and then dried to obtain camphenyl S...

Embodiment 1

[0025] Embodiment 1: the synthetic general method that contains camphenyl Schiff base compound (aniline and p-chloroaniline)

[0026] (1) Add 0.05mol of camphenal, 0.055mol of p-chloroaniline and 30ml of cyclohexane in a 150ml conical flask equipped with a water separator, fill the water separator with water-carrying agent, stir and reflux for 2 hours , track the reaction process with the gas phase until the product content no longer increases;

[0027] (2) The cyclohexane in the reactant is steamed out, and the target product camphenal aniline Schiff base and camphenal aniline Schiff base are distilled off under reduced pressure.

[0028] The product is as follows:

[0029] ① Camphenaldehyde aniline Schiff base, molecular formula: C 17 h 21 N, molecular weight: 239.17, brown liquid, b.p. = 165-167°C / 200Pa, purity 95.65%, yield 73%, the attribution of structural analysis spectrum data is as follows:

[0030] FT-IR,ν max (cm -1 ): 2961, 2919, 2868 (C-H), 1648 (C=N), 1602,...

Embodiment 2

[0039] Embodiment 2: the synthetic general method that contains camphenyl Schiff base compound (o-toluidine, p-toluidine, p-bromoaniline, o-chloroaniline, p-methoxyaniline, m-nitroaniline, p-nitroaniline)

[0040] (1) Add 0.05mol of camphenal, 0.055mol of aromatic amine and 30ml of cyclohexane in the 150ml Erlenmeyer flask equipped with water separator, fill up the water-carrying agent in the water separator, stir and reflux after 2h, Use the gas phase to track the reaction progress until the product content no longer increases;

[0041] (2) Distill the cyclohexane in the reactant, add ethanol, let it crystallize naturally, filter out the crystal, then recrystallize in ethanol, filter under reduced pressure, rinse the solid with cold ether, and dry in vacuo , to obtain a solid powder form of camphenal condensed substituted aniline Schiff base.

[0042] The product is as follows:

[0043] ① Camphen aldehyde p-toluidine Schiff base, molecular formula: C 18 h 23 N, molecular ...

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Abstract

The invention discloses a method for synthesizing a Schiff base compound containing camphenyl. The method includes the following specific synthetic steps that camphorenal is used as a raw material, an aromatic amine compound is added in a reaction device containing organic solvent, the camphorenal and aromatic amine are fed according to the molar ratio of 1:1-1.1, stirring reflux is conducted for 2-3 hours, a reacted product is purified through solvent, and then drying is carried out, so that the Schiff base compound containing the camphenyl is obtained. According to the preparation method, the camphorenal is used as the raw material to be reacted with the aromatic amine compound so that the Schiff base compound can be obtained, camphene radicals are introduced into Schiff base, and finally the aromatic amine Schiff base containing the camphenyl is obtained. The experimental steps are simple and convenient, the reaction condition is moderate, time is short, the yield is high, safety and environmental protection are achieved, aftertreatment is convenient, and secondary pollution is small.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to a synthesis method of camphenyl Schiff base compounds. Background technique [0002] Most organic amine compounds have certain biological activity, and can also be used as intermediates in the synthesis of amides, Schiff bases, and quaternary ammonium salts. Schiff base is a kind of compound with C=N structure. It was first synthesized by H. Schiff in 1864. Its synthesis method is simple and can provide lone electron pairs. It can be combined with metals such as iron, cobalt, nickel, copper, etc. and rare earths. Metals etc. form complexes. (Journal of Chifeng University (Natural Science Edition), 2013, 29(11): 16-17.) It is found that Schiff bases and their complexes have great potential in the fields of pharmacy, catalysis, analytical chemistry, corrosion, liquid crystal materials and photochromism. Important applications: In the medical field, Schiff base derivati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C249/02C07C251/14
Inventor 范国荣翁玉辉肖转泉陈金珠王鹏陈尚钘王宗德
Owner JIANGXI AGRICULTURAL UNIVERSITY
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