Preparation and application of a kind of 6-chloro-3-[(2-hydroxy-4-diethylaminobenzylidene)amino]coumarin

A technology of diethylaminobenzylidene and coumarin, applied in fluorescence/phosphorescence, instrumentation, organic chemistry, etc., can solve problems such as low sensitivity and selectivity of optical sensing, difficult purification and separation, and complex synthesis process , to achieve the effects of less raw material consumption, good recognition selectivity, and simple synthesis method

Active Publication Date: 2019-06-04
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The purpose of the present invention is to overcome the expensive raw materials of existing cobalt ion colorimetric and fluorescent molecular probes, complex synthesis process, high reaction temperature, long reaction time, high energy consumption, difficult purification and separation, low optical sensing sensitivity and selectivity and other shortcomings, through simple reaction, relatively mild reaction conditions, using green and non-polluting solvents, high yield and purity to prepare and isolate the molecular probe of coumarin Schiff base compound with excellent performance, so that the molecular probe can be used with the naked eye , high sensitivity, single selective recognition and detection of cobalt ions

Method used

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  • Preparation and application of a kind of 6-chloro-3-[(2-hydroxy-4-diethylaminobenzylidene)amino]coumarin
  • Preparation and application of a kind of 6-chloro-3-[(2-hydroxy-4-diethylaminobenzylidene)amino]coumarin
  • Preparation and application of a kind of 6-chloro-3-[(2-hydroxy-4-diethylaminobenzylidene)amino]coumarin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] (1) Accurately weigh 3.13g of 5-chlorosalicylaldehyde, 2.34g of N-acetylglycine, and 3.28g of anhydrous sodium acetate, dissolve them in 40mL of acetic anhydride, and reflux at 138°C for 10 hours. After the reaction Add 10 mL of ice water, vacuum-dry at 25° C. for 10 hours after suction filtration to obtain an intermediate product.

[0033] (2) The intermediate product is placed in 60 mL of a mixed solvent of concentrated hydrochloric acid and ethanol with a volume ratio of 1.5:1, heated to reflux at a temperature of 70 ° C for 5 hours, then cooled, and the acidity is adjusted to 5.5 with a NaOH solution with a mass concentration of 30%. , precipitated out, filtered, and the product was vacuum-dried at 25°C for 24 hours and then recrystallized with ethanol to obtain 3-amino-6-chlorocoumarin;

[0034] (3) Accurately weigh 0.5g of 3-amino-6-chlorocoumarin and 0.5g of 4-diethylaminosalicylaldehyde and dissolve them in 30mL of ethanol, condense and reflux for 5 hours at 70°...

Embodiment 2

[0036](1) Accurately weigh 3.13g of 5-chlorosalicylaldehyde, 2.34g of N-acetylglycine, and 4.92g of anhydrous sodium acetate, dissolve them in 45mL of acetic anhydride, and reflux at 139°C for 9 hours. After the reaction Add 12 mL of ice water, vacuum-dry at 30° C. for 9 hours after suction filtration to obtain an intermediate product.

[0037] (2) The intermediate product is placed in 60 mL of a mixed solvent of concentrated hydrochloric acid and ethanol with a volume ratio of 1.5:1, heated to reflux at a temperature of 75 ° C for 5 hours and then cooled, and the acidity is adjusted to 6.0 with a NaOH solution with a mass concentration of 30%. , precipitated, filtered, and the product was vacuum-dried at 30°C for 20 hours and then recrystallized with ethanol to obtain 3-amino-6-chlorocoumarin;

[0038] (3) Accurately weigh 0.5g of 3-amino-6-chlorocoumarin and 0.6g of 4-diethylaminosalicylaldehyde and dissolve them in 35mL of ethanol, condense and reflux at 75°C for 4 hours, a...

Embodiment 3

[0040] (1) Accurately weigh 3.13g of 5-chlorosalicylaldehyde, 2.34g of N-acetylglycine, and 4.10g of anhydrous sodium acetate, dissolve them in 45mL of acetic anhydride, and reflux at 140°C for 7 hours. After the reaction Add 10 mL of ice water, vacuum-dry at 35° C. for 8 hours after suction filtration to obtain an intermediate product.

[0041] (2) The intermediate product is placed in 60 mL of a mixed solvent of concentrated hydrochloric acid and ethanol with a volume ratio of 2:1, heated to reflux at 80 ° C for 4 hours, then cooled, and the acidity is adjusted to 6.5 with a NaOH solution with a mass concentration of 30%. , precipitated, filtered, and the product was vacuum-dried at 35°C for 18 hours and then recrystallized with ethanol to obtain 3-amino-6-chlorocoumarin;

[0042] (3) Accurately weigh 0.5g of 3-amino-6-chlorocoumarin and 0.5g of 4-diethylaminosalicylaldehyde and dissolve them in 30mL of ethanol, condense and reflux for 4 hours at 80°C, and suction filter aft...

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Abstract

The invention discloses preparation and application of 6-chloro-3-[(2-hydroxy-4-diethylin benzylidene)amino]coumarin, and belongs to the technical fields of inorganic material synthesis and application. The 6-chloro-3-[(2-hydroxy-4-diethylin benzylidene)amino]coumarin is prepared by firstly synthesizing 3-amino-6-chlorocoumarin from 5-chloro salicylaldehyde, acetoglycocoll and anhydrous sodium acetate, and then reacting with 4-diethylin salicylaldehyde. The 6-chloro-3-[(2-hydroxy-4-diethylin benzylidene)amino]coumarin synthesized in the invention is a novel cobalt ions colorimetric recognition molecular probe, and is stable in structure, simple in preparation method, mild in reaction conditions, green, non-pollution and high in yield; and moreover, the 6-chloro-3-[(2-hydroxy-4-diethylin benzylidene)amino]coumarin has a good naked eye recognition effect for cobalt ions, is high in sensitivity and high in special selectivity, can be used for trace detection of cobalt ions, and is an ion colorimetric sensing material with important application values.

Description

technical field [0001] The invention belongs to the technical field of synthesis and application of inorganic materials, and in particular relates to a method for easily preparing a coumarin Schiff base colorimetric sensing material and its application. Background technique [0002] The identification of ions in organisms and in the environment is of great significance in the fields of life sciences, food industry, environmental protection, and pharmacology. As we all know, cobalt is an essential trace element in the human body and is closely related to human health. Its main function is to form vitamin B12 necessary for the metabolism of folic acid and fatty acids and realize the transfer of methyl groups. Studies have shown that the concentration of cobalt ions can lead to the occurrence of various diseases. For example, insufficient intake of cobalt in the human body can cause cardiovascular disease, while excessive intake of cobalt ions can cause cobalt poisoning. Theref...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/14C09K11/06G01N21/31G01N21/64
CPCC07D311/14C09K11/06C09K2211/1007C09K2211/1088G01N21/314G01N21/643G01N2021/3155
Inventor 吴芳辉徐帆孙文斌魏先文杨俊卿
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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