4-amino-5-substituted-1,2,4-triazole-3-thione Schiff base and preparation method thereof

An amino, thione technology, applied in the direction of organic chemistry, etc., can solve the problems of low yield, large solvent usage, long reaction time, etc.

Active Publication Date: 2014-07-23
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation of the azole Schiff bases reported in the existing literature mostly uses ethanol, DMF, etc. as the reaction medium, with acid as the catalyst, and is prepared by conventional heating methods, so there are disadvantages such as long reaction time, low yield, and large solvent usage.

Method used

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  • 4-amino-5-substituted-1,2,4-triazole-3-thione Schiff base and preparation method thereof
  • 4-amino-5-substituted-1,2,4-triazole-3-thione Schiff base and preparation method thereof
  • 4-amino-5-substituted-1,2,4-triazole-3-thione Schiff base and preparation method thereof

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preparation example Construction

[0028] Wherein the preparation method of 4-amino-5-substituted-1,2,4-triazole-3-thione as raw material comprises the following steps:

[0029] 1) Add A mol carboxylic acid, B mol symmetrical thiosemicarbazide and C mol phosphorus pentachloride to a dry mortar, grind at room temperature for 5-10 minutes until the raw materials are completely reacted, and the crude product is obtained after standing; where A: B:C=(1~1.2):1:(1~1.2);

[0030] 2) Add an alkaline solution to the crude product until the pH of the resulting mixture is neutral, then suction-filter the mixture and recrystallize the filter cake to obtain 4-amino-5-substituted-1,2, 4-Triazole-3-thione.

[0031]The carboxylic acid includes benzoic acid, p-toluic acid, o-toluic acid, m-toluic acid, p-methoxybenzoic acid, m-methoxybenzoic acid, 4-fluorobenzoic acid, 2-fluoro Benzoic acid, p-aminobenzoic acid, m-aminobenzoic acid, anthranilic acid, p-chlorobenzoic acid, o-chlorobenzoic acid, 2,4-dichlorobenzoic acid, p-nitr...

Embodiment 1

[0034] 1) Add 0.005mol 4-amino-5-phenyl-1,2,4-triazole-3-thione, 0.0055mol benzaldehyde and 0.0055mol p-toluenesulfonic acid to a dry mortar, and grind for 10min at room temperature, At this time, TLC monitoring showed that the raw material point of 4-amino-5-phenyl-1,2,4-triazole-3-thione disappeared, indicating that the raw material was completely reacted, and then left to stand for 30min to obtain the mixture; wherein the developer of TLC It is a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:3;

[0035] 2) Dissolve the mixture in a small amount of absolute ethanol, vacuum filter, wash the filter cake twice with a small amount of absolute ethanol, mix the eluate from the two times with the filtrate and concentrate to dryness to obtain high-purity 4-amino- 5-Phenyl-1,2,4-triazole-3-thione Schiff base whose R' group is -H. m.p.: 169-171°C, yield 87%.

[0036] IR (KBr tablet): 3172(N-H), 2990(=C-H, Ar-H), 1600(C=N), 1595, 1540, 1489, 1451(Ar), 13...

Embodiment 2

[0038] 1) Add 0.005mol 4-amino-5-p-chlorophenyl-1,2,4-triazole-3-thione, 0.0055mol benzaldehyde and 0.0055mol p-toluenesulfonic acid to a dry mortar and grind at room temperature 10min, at this time, TLC monitoring showed that the raw material point of 4-amino-5-p-chlorophenyl-1,2,4-triazole-3-thione disappeared, indicating that the raw material was completely reacted, and then left to stand for 30min to obtain a mixture; The developer of TLC is a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:3;

[0039] 2) Dissolve the mixture in a small amount of absolute ethanol, vacuum filter, wash the filter cake twice with a small amount of absolute ethanol, mix the eluate from the two times with the filtrate and concentrate to dryness to obtain high-purity 4-amino- 5-p-Chlorophenyl-1,2,4-triazole-3-thione Schiff base, the R' group is -H. m.p.: 172-174°C, yield 86.7%.

[0040] IR (KBr tablet): 3169(N-H), 2980(=C-H, Ar-H), 1591(C=N), 1580, 1529, 1489, 1452(...

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Abstract

The invention relates to a 4-amino-5-substituted-1,2,4-triazole-3-thione Schiff base and a preparation method thereof. The preparation method comprises: adding A mol of 4-amino-5-substituted-1,2,4-triazole-3-thione, B mol of benzaldehyde or substituted benzaldehyde and C mol of p-toluene sulfonic acid to a dried reaction container, grinding the raw materials at a room temperature until the raw materials completely react, and standing to obtain a crude product, wherein a ratio of A to B to C is 1:(1-1.2):(1-1.2); and dissolving the crude product with a solvent, carrying out suction filtration, and concentrating the filtrate until achieving a dry state to obtain the 4-amino-5-substituted-1,2,4-triazole-3-thione Schiff base. According to the present invention, the preparation method adopts the solid phase reaction, the reaction time is short, the reaction conditions are mild, the equipment requirements are low, the operations are simple, the post-treatment is simple, the solvent is not required, characteristics of green, economy and environmental protection are provided, and the yield of the target product is up to more than 86%.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and particularly relates to a 4-amino-5-substituted-1,2,4-triazole-3-thione Schiff base and a preparation method thereof. Background technique [0002] Schiff base compounds refer to a class of methyleneamine-containing compounds synthesized from primary amines and active carbonyl compounds. There are N atoms with strong coordination ability in its structure, and N atoms that may contain lone pairs of electrons outside the ring, 0, S and other heteroatoms, the Schiff base compound is a kind of organic ligand with excellent performance. Since the metal ion contains empty d orbitals, it can accept the lone electron pair provided by the heteroatom of the ligand, so that the metal and the heteroatom can be coordinated to form metal complexes. Functionalized Schiff alkali metal complexes are stable and rich in structure and widely used in many fields. Schiff base compounds and their complexes with ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/12
CPCC07D249/12
Inventor 刘玉婷宋思梦刘蓓蓓尹大伟杨阿宁王金玉吕博
Owner SHAANXI UNIV OF SCI & TECH
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