CN107619380A - A kind of single Schiff base derivatives and preparation method thereof - Google Patents

A kind of single Schiff base derivatives and preparation method thereof Download PDF

Info

Publication number
CN107619380A
CN107619380A CN201711105242.7A CN201711105242A CN107619380A CN 107619380 A CN107619380 A CN 107619380A CN 201711105242 A CN201711105242 A CN 201711105242A CN 107619380 A CN107619380 A CN 107619380A
Authority
CN
China
Prior art keywords
schiff base
reaction
base derivatives
preparation
single schiff
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201711105242.7A
Other languages
Chinese (zh)
Inventor
黄杰
郑莘月
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chongqing University of Technology
Original Assignee
Chongqing University of Technology
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chongqing University of Technology filed Critical Chongqing University of Technology
Priority to CN201711105242.7A priority Critical patent/CN107619380A/en
Publication of CN107619380A publication Critical patent/CN107619380A/en
Pending legal-status Critical Current

Links

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a kind of single Schiff base derivatives and preparation method thereof, the structural formula of single Schiff base derivatives is:

Description

A kind of single Schiff base derivatives and preparation method thereof
Technical field
The invention belongs to organic synthesis field, more particularly to a kind of single Schiff base derivatives and preparation method thereof.
Background technology
Schiff bases is primarily referred to as a kind of organic compound containing imines or azomethine group, typically by containing active carbonyl Compound and the primary amine condensation of base form.Schiff bases and its complex, have excellent antibacterial, anticancer, antiviral, weeding etc. raw Thing activity, and the performance such as special photoelectromagnetic.Therefore, draw in recent years in fields such as medicine, biology, catalysis and functional materials The widely studied interest of researcher is played.
However, the traditional preparation methods of schiff bases be usually in organic solvent, by the compound containing active carbonyl with Amine carries out condensation reaction and obtained, and reaction needs to use organic solvent, catalyst, and the reaction time is longer, and side reaction is more, and is difficult to Separating-purifying, there is the deficiencies of power consumption is high, pollution is larger.Therefore, new Schiff base derivatives are developed, and green, The low preparation method of high-efficient simple, energy consumption is significant.
Publication No. CN106518726A patent of invention discloses a kind of aryl Schiff base derivatives and preparation method thereof, This method mixes above-mentioned reaction raw materials and appropriate water in hydrothermal reaction kettle using NPD and benzaldehyde as raw material Close, reacted under high temperature by the high diffusivity coefficient and strong solubility of high-temperature water.The patented method is without using organic solvent And catalyst, mild condition, but the aryl Schiff base derivatives low yield prepared, typically 20~30% or so.
The content of the invention
For deficiencies of the prior art, it is an object of the invention to provide a kind of single Schiff base derivatives and its system Preparation Method, solve the problems, such as that existing method prepares Schiff base derivatives and needs to use organic solvent, catalyst.
To achieve the above object, the present invention adopts the following technical scheme that:
Single Schiff base derivatives of the present invention, shown in its structural formula such as formula (I):
The preparation method of single Schiff base derivatives is as described above:It is 1 by mol ratio:1~2 3,4- diaminotoluenes It is placed in hydrothermal reaction kettle and is reacted with benzaldehyde, wherein, the compactedness of the hydrothermal reaction kettle reclaimed water is 30~70%, instead It is 90~180 DEG C to answer temperature, and the reaction time is 180~480min, after completion of the reaction, reaction product is filtered, it is dry, tie again Crystalline substance, that is, obtain described single Schiff base derivatives.
The reaction equation that the present invention prepares single Schiff base derivatives is as follows:
Preferably, the mol ratio of 3, the 4- diaminotoluenes and benzaldehyde is 1:1.5~2.
Preferably, the reaction temperature is 150~170 DEG C.
Preferably, the reaction time is 300~420min.
Preferably, the compactedness is 50~70%.
Under above-mentioned optimum condition, the yield of Schiff base derivatives prepared by the present invention is greatly improved.
Preferably, ethanol or ethyl acetate that the solvent that recrystallization uses is 95%.The present invention by preferable solvent, The purity and yield of product can be effectively improved, recrystallization method is conventional method.
Schiff base derivatives prepared by the present invention can be applied in the fields such as medicine, catalysis and functional material.
Compared with prior art, the present invention has the advantages that:
1st, the preparation method of the single Schiff base derivatives of the present invention replaces Conventional glass instrument as reaction using hydrothermal reaction kettle Device, high temperature high voltage resistant, conventional organic solvent is replaced as reaction medium using water, it is nontoxic, and without using any catalyst, Reaction raw materials are mixed with suitable quantity of water in hydrothermal reaction kettle, are placed under the subcritical or supercritical temperature of water, it is main using high The high diffusivity coefficient and strong solubility of warm water, so that reaction is efficient, easily carries out.The preparation method is green, condition Gently, the reaction time is short, and accessory substance is few and is easily isolated purification, and yield is high, is easy to operate and control, required equipment and raw material are easy , it is cheap.
2nd, the Schiff base derivatives that prepare of the present invention, due to the connection of imines both ends it is on the one hand the structure containing phenyl ring, Chemical stability is good, on the other hand, is dissolved in common a variety of organic solvents, dissolubility is good, and has photoluminescent property, in organic hair The fields such as optical function material have a good application prospect.
3rd, the present invention reduces the generation of side reaction, significantly by the selection and the optimization of reaction condition to reaction raw materials The yield of the Schiff base derivatives of preparation is improved, maximum output is up to 65.6%, hence it is evident that prepare higher than existing congenic method The yield of Schiff base derivatives.
Brief description of the drawings
Fig. 1 is the infrared spectrogram of Schiff base derivatives prepared by embodiment 1;
Fig. 2 is the fluorescence emission spectrogram of compound of Schiff base derivatives prepared by embodiment 1.
Embodiment
The present invention is described in further detail with reference to specific embodiment.
Embodiment 1
In 25mL hydrothermal reaction kettle, 10mL water (compactedness 40%) is added, adds 2mmol 3,4- diaminos The benzaldehyde of base toluene and 2mmol, reacted 150 minutes at 150 DEG C.It is right after reactor is cooled into room temperature after reaction terminates Reaction product filtered, dried, being recrystallized successively, is dried, that is, obtains target product, recrystallized in the present embodiment use it is molten Agent is ethyl acetate.
Embodiment 2
In 50mL hydrothermal reaction kettle, 25mL water (compactedness 50%) is added, adds 5mmol 3,4- diaminos Base toluene and 5mmol benzaldehydes, reacted 240 minutes at 100 DEG C.After reaction terminates, after reactor is cooled into room temperature, to anti- Answer product filtered, dried successively, recrystallized, dry, that is, obtain target product, the solvent used is recrystallized in the present embodiment For 95% ethanol.
Embodiment 3
In 50mL hydrothermal reaction kettle, 30mL water (compactedness 60%) is added, adds 1mmol 3,4- diaminos Base toluene and 1.5mmol benzaldehydes, reacted 360 minutes at 140 DEG C.It is right after reactor is cooled into room temperature after reaction terminates Reaction product filtered, dried, being recrystallized successively, is dried, that is, obtains target product, recrystallized in the present embodiment use it is molten Agent is ethyl acetate.
Embodiment 4~12
The operating method of embodiment 4~12 is same as Example 1, and difference is design parameter difference, is specifically shown in Table 1.
The relevant parameter of 1 embodiment of table 1~12
By above example, Schiff base derivatives yield prepared by the present invention reaches as high as 65.6%.
Fig. 1 is the infrared spectrogram of single Schiff base derivatives prepared by embodiment 1, as seen from the figure, single schiff bases of preparation Derivative is in about 1625cm-1There is the telescope features absworption peak of schiff bases-C=N- groups, thus illustrate target product Schiff Alkali is successfully prepared.
Fig. 2 is the single Schiff base derivatives that prepare of embodiment 1 in absolute ethyl alcohol (solid line in figure) and tetrahydrofuran (void in figure Line) in fluorescence emission spectrogram of compound (excitation wavelength 300nm), as shown in Figure 2, single Schiff base derivatives for preparing of the present invention exist There is certain luminosity in absolute ethyl alcohol and tetrahydrofuran solution, have in the fields such as luminous organic material and potentially should With value.
The above embodiment of the present invention is only example to illustrate the invention, and is not the implementation to the present invention The restriction of mode.For those of ordinary skill in the field, other can also be made not on the basis of the above description With the change and variation of form.Here all embodiments can not be exhaustive.It is every to belong to technical scheme Row of the obvious changes or variations amplified out still in protection scope of the present invention.

Claims (7)

  1. A kind of 1. single Schiff base derivatives as shown in formula (I):
  2. A kind of 2. method for preparing single Schiff base derivatives as claimed in claim 1, it is characterised in that by mol ratio be 1:1 ~23,4- diaminotoluenes and benzaldehyde, which is placed in hydrothermal reaction kettle, to be reacted, wherein, the hydrothermal reaction kettle reclaimed water Compactedness is 30~70%, and reaction temperature is 90~180 DEG C, and the reaction time is 180~480min, after completion of the reaction, reaction production Thing is filtered, dry, recrystallization, that is, obtains described single Schiff base derivatives.
  3. 3. the preparation method of single Schiff base derivatives according to claim 2, it is characterised in that 3, the 4- diaminourea first The mol ratio of benzene and benzaldehyde is 1:1.5~2.
  4. 4. the preparation method of single Schiff base derivatives according to claim 2, it is characterised in that the reaction temperature is 150~170 DEG C.
  5. 5. the preparation method of single Schiff base derivatives according to claim 2, it is characterised in that the reaction time is 300~420min.
  6. 6. the preparation method of single Schiff base derivatives according to claim 2, it is characterised in that the compactedness be 50~ 70%.
  7. 7. the preparation method of single Schiff base derivatives according to claim 2, it is characterised in that recrystallize the solvent used For 95% ethanol or ethyl acetate.
CN201711105242.7A 2017-11-10 2017-11-10 A kind of single Schiff base derivatives and preparation method thereof Pending CN107619380A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201711105242.7A CN107619380A (en) 2017-11-10 2017-11-10 A kind of single Schiff base derivatives and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201711105242.7A CN107619380A (en) 2017-11-10 2017-11-10 A kind of single Schiff base derivatives and preparation method thereof

Publications (1)

Publication Number Publication Date
CN107619380A true CN107619380A (en) 2018-01-23

Family

ID=61098702

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201711105242.7A Pending CN107619380A (en) 2017-11-10 2017-11-10 A kind of single Schiff base derivatives and preparation method thereof

Country Status (1)

Country Link
CN (1) CN107619380A (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106496065A (en) * 2016-10-31 2017-03-15 重庆理工大学 A kind of o-phenylenediamine Schiff base derivatives and preparation method and application
CN106518726A (en) * 2016-10-31 2017-03-22 重庆理工大学 Aryl Schiff base derivative and preparation method and application thereof
CN106748879A (en) * 2016-10-31 2017-05-31 重庆理工大学 P-nitrobenzaldehyde Schiff base derivative and preparation method and application thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106496065A (en) * 2016-10-31 2017-03-15 重庆理工大学 A kind of o-phenylenediamine Schiff base derivatives and preparation method and application
CN106518726A (en) * 2016-10-31 2017-03-22 重庆理工大学 Aryl Schiff base derivative and preparation method and application thereof
CN106748879A (en) * 2016-10-31 2017-05-31 重庆理工大学 P-nitrobenzaldehyde Schiff base derivative and preparation method and application thereof

Similar Documents

Publication Publication Date Title
Wang et al. GAP chemistry for pyrrolyl coumarin derivatives: a highly efficient one-pot synthesis under catalyst-free conditions
CN103320118A (en) Schiff base cooper ion fluorescence probe and preparation method thereof
CN106748879B (en) P-nitrobenzaldehyde Schiff base derivative and preparation method and application thereof
CN106518726B (en) Aryl Schiff base derivative and preparation method and application thereof
CN106496065B (en) A kind of o-phenylenediamine Schiff base derivatives and the preparation method and application thereof
CN107459488B (en) Isolonglifolane base and pyrimidine -2- amine Schiff bases fluorescent chemicals and preparation method thereof
CN101717320A (en) Preparing method of mannich base
CN107673991A (en) A kind of Schiff base derivatives and preparation method thereof
CN107619380A (en) A kind of single Schiff base derivatives and preparation method thereof
CN101921258B (en) Preparation method of 5-( arylmethylene) meldrum's acid
CN105837568B (en) A kind of fluorenyl β carbolines class compound, its application and preparation method as luminous organic material and aggregation inducing Fluorescence Increasing material
CN101463011A (en) Process for synthesizing 3,4-dihydropyrimidine-2-keto
CN104610267B (en) Method for efficiently synthesizing 6-alkyl pyrazolo [1,5-c ] quinazoline framework compound under non-catalytic condition
CN107673992A (en) A kind of ortho-aminophenol Schiff base derivatives and preparation method thereof
CN108069859A (en) The application of Azacyclyl terephthalic acid (TPA) ester derivant and its compound crystal in terms of Amplified Spontaneous Emission
CN106632071B (en) Method for preparing 3, 4-dihydropyrimidine-2-one derivative by promoting high-efficiency catalysis of titanocene dichloride with ethanol
CN102807586B (en) Preparation method of fosfomycin amine salt
CN104059109A (en) 3-[4-(2-amino-5-substituted-[1,3,4]thiadiazolyl)-phenyl]-1-ferrocenyl-acrylketone and preparation method thereof
CN103664931A (en) Schiff base compound containing benzothiazole ring and imidazole ring, and preparation method thereof
CN102863451A (en) Preparation method and usage of triphenylamine molecule-containing chromene and naphthyridine fluorescent compound
CN107954960B (en) Synthetic method of 1,3-dihydroisobenzofuran compound
Liu et al. A general and efficient method for synthesis of enaminones and enamino esters catalyzed by NbCl 5 under solvent-free conditions
CN103254112A (en) Bisindole alkaloid derivative, and synthesis method and application thereof
CN107915748A (en) A kind of preparation method of 4 (tert-butyl group) 1 phenylimidazoles simultaneously [4,5,1 kl] phenoxazine
CN103553985B (en) 4-methoxy-N,N-bisubstituted phenyl-1,3-benzene bisulfonamide compound and application thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
RJ01 Rejection of invention patent application after publication
RJ01 Rejection of invention patent application after publication

Application publication date: 20180123