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A kind of synthetic method containing camphenyl schiff base compound

A synthesis method and compound technology are applied in the field of synthesis of camphenyl-containing Schiff base compounds, can solve the problems such as there is no synthetic method for camphenyl-containing Schiff base compounds, and achieve high yield, little secondary pollution, The effect of mild reaction conditions

Active Publication Date: 2017-08-25
JIANGXI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • A kind of synthetic method containing camphenyl schiff base compound
  • A kind of synthetic method containing camphenyl schiff base compound
  • A kind of synthetic method containing camphenyl schiff base compound

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preparation example Construction

[0019] A kind of synthetic method containing camphenyl Schiff base compound, is characterized in that, concrete synthesis step is as follows:

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

[0021] The molar ratio of camphenal and aromatic amine is 1: 1~1.1 for feeding, then adding organic solvent benzene or cyclohexane, stirring and refluxing for 2~3h, and tracking the reaction progress in gas phase until the content of the target product no longer increases;

[0022] (2) benzene or cycloethane solvent in the above-mentioned reaction solution are steamed, and the thick product obtained is purified with methanol or ethanol, and then dried to obtain camphenyl Schiff base compounds, and its...

Embodiment 1

[0025] Embodiment 1: General method of synthesis of camphenyl-containing Schiff base compounds (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, add water-carrying agent in the water separator, stir and reflux for 2h , use the gas phase to track the reaction process until the product content no longer increases;

[0027] (2) The cyclohexane in the reactant is evaporated, and the target products, camphenal aniline Schiff base and camphenal o-toluidine Schiff base, are distilled off under reduced pressure.

[0028] The product is as follows:

[0029] ①Camhenal aniline Schiff base, molecular formula: C 17 H 21 N, molecular weight: 239.17, brown liquid, b.p.=165~167℃ / 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, 1586, 1484...

Embodiment 2

[0039] Embodiment 2: General method for synthesis of camphenyl Schiff base compounds (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 a 150ml conical flask equipped with a water separator, add water-carrying agent in the water separator, stir and reflux for 2h, Follow the progress of the reaction with the gas phase until the product content no longer increases;

[0041] (2) The cyclohexane in the reactant was steamed, ethanol was added, placed to allow natural crystallization, after the crystals were filtered out, recrystallized in ethanol, filtered under reduced pressure, the solid was rinsed with cold ether, and dried in vacuo , to obtain a solid powdery camphenal acetal substituted aniline Schiff base.

[0042] The product is as follows:

[0043] ① camphenal acetal p-toluidine Schiff base, molecular formula: C 18 H 23 ...

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Abstract

The invention discloses a synthesis method of a camphenyl-based Schiff base compound. The specific synthesis steps are as follows: taking camphenal as a raw material, adding aromatic amine compounds to a reaction device in an organic solvent, and molar amounts of camphenal and aromatic amine The ratio is 1:1-1.1 for feeding, stirring and reflux for 2-3 hours, the product after the reaction is purified with a solvent, and then dried to obtain camphenyl Schiff base compounds. The preparation method of the present invention uses amphene aldehyde as a raw material, reacts with aromatic amine compounds to obtain Schiff base compounds, introduces amphene groups into the Schiff base, and finally obtains amphene group-containing aromatic amine Schiff bases, and the experimental steps are simple and convenient. The reaction condition is mild, the time is short, the yield is high, the reaction is safe and environmentally friendly, the post-treatment is convenient, and the secondary pollution is small.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to a method for synthesizing a camphenyl Schiff base compound. 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 bases are a class of compounds with a C=N structure. They were first synthesized by H. Schiff in 1864. The synthesis method is simple and can provide lone electron pairs, which can interact 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.) The study found that Schiff bases and their complexes have important properties in the fields of pharmacy, catalysis, analytical chemistry, corrosion, liquid crystal materials and photochromism. Important applications; in the medical fie...

Claims

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Application Information

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Patent Type & Authority Patents(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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