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Method for synthesizing thiazole derivative containing acetophenone triazole group in ultrasonic solvent-free manner

An acetophenone triazole group, ultrasonic technology, applied in the direction of organic chemistry, etc., can solve the problems of unrealistic industrial production, difficult to handle, and toxicity of dimethyl sulfoxide, etc., achieve good industrial application prospects, reduce steps, methods simple and easy effects

Active Publication Date: 2018-02-13
HENAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Dimethyl sulfoxide is toxic, has a high boiling point, and can be mixed with water in any proportion. Dimethyl sulfoxide in industrial sewage is difficult to treat. In addition, the target product is separated by column chromatography. This synthesis process cannot be industrialized. Production

Method used

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  • Method for synthesizing thiazole derivative containing acetophenone triazole group in ultrasonic solvent-free manner

Examples

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Effect test

Embodiment 1

[0025] Accurately weigh homemade α-(1H-1,2,4-triazol-1-yl)acetophenone (synthetic method: take the same molar number of α-bromoacetophenone and 1H-1,2,4 - Triazole and acetone, dropwise add triethylamine of the same number of moles at a certain speed at 0°C. Continue to stir until the white needles no longer continue to precipitate in large quantities after the dropwise addition is completed. Filter off the triethylamine bromate solid, and the filtrate Concentrate to obtain a yellow viscous substance, then dissolve it with chloroform, wash it in a separatory funnel, separate the organic phase, evaporate the chloroform to obtain a light yellow solid, and then recrystallize it with ethanol to obtain a white flaky crystal, the yield is 63.5%.) 1.87 g (0.01mol), 1.37g (0.01mol, slightly excess) phenyl isothiocyanate and 0.68g potassium hydroxide, mix thoroughly in a mortar, transfer to a round bottom flask, fix it in an ultrasonic oscillator Oscillate for 0.5h. Insert an ultrason...

Embodiment 2

[0031]Accurately weigh 1.87 g (0.01 mol) of α-(1H-1,2,4-triazol-1-yl) acetophenone, 1.35 g (0.01 mol) phenyl isothiocyanate and 0.68 g potassium hydroxide, Mix thoroughly in a mortar and transfer to a round-bottomed flask, and fix it in an ultrasonic oscillator to vibrate for 0.5h. Insert an ultrasonic dry-mist nozzle with an atomization particle size of 1-10 µm into the mouth of the round-bottom flask and connect it to the atomizer, and spray α-bromo-p-chloroacetophenone in the form of liquid mist regularly. Set the frequency to 20kHZ~25kHZ, and turn on the ultrasonic response under the rated power of 400w. After the shaking was started, a nebulized α-bromo-p-chloroacetophenone was sprayed into the solids in the flask. When the mist is thick, stop for a period of time and continue to spray α-bromo-p-chloroacetophenone to observe the color change of the reactant solid. When the color of the solid reactant turns yellow completely, and the color does not change, stop spraying ...

Embodiment 3

[0037] Accurately weigh 1.87 g (0.01 mol) of α-(1H-1,2,4-triazol-1-yl) acetophenone, 1.35 g (0.01 mol) phenyl isothiocyanate and 0.68 g (0.012 mol) Potassium hydroxide, mixed thoroughly in a mortar, then transferred to a round bottom flask, fixed in an ultrasonic oscillator and oscillated for 0.5h. Insert an ultrasonic dry-mist nozzle with an atomization particle size of 1-10 μm into the mouth of the round-bottom flask and connect it to the atomizer, and regularly spray α-bromo-2,5-dichloroacetophenone in the form of liquid mist. Set the frequency to 20kHZ~25kHZ, and turn on the ultrasonic response under the rated power of 400w. After the shaking was started, a mist of α-bromo-2,5-dichloroacetophenone was sprayed into the solids in the flask. When the mist is thick, stop for a period of time and continue to spray α-bromo-2,5-dichloroacetophenone, and observe the color change of the reactant solid. When the color of the solid reactant has completely changed to yellow and the ...

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Abstract

The invention relates to a method for synthesizing a thiazole derivative containing an acetophenone triazole group in an ultrasonic solvent-free manner. Three solids of alpha-(1H-1,2,4-triazol-1-yl)acetophenone, phenyl isothiocyanate and potassium hydroxide are adopted as raw materials; foggy alpha-bromoacetophenone is enabled to react with the solids under ultrasonic action by adopting a liquid spraying manner; the reaction is promoted by adopting the solvent-free ultrasonic manner, and the method has the advantages of being simple in reaction equipment, higher in yield, quicker in speed, easy to operate, free from other side-products, free from a solvent, free from pollution and easy in separation and purification, and the like.

Description

technical field [0001] The invention relates to the technical field of synthesizing thiazole compounds containing triazole rings, in particular to an ultrasonic solvent-free method for synthesizing thiazole derivatives containing acetophenone triazole groups. Background technique [0002] Thiazole rings are an important class of five-membered aromatic heterocyclic rings containing nitrogen and sulfur heteroatoms, which have abundant electrons, coordination with metal ions and π-π stacking, easy formation of hydrogen bonds, electrostatic and hydrophobic interactions, etc. Valence bond interaction, such a special structure endows thiazole compounds with many special properties, and has a wide range of potential applications in many fields, and the synthesis methods are increasing day by day. Especially with a series of thiazole compounds successfully used in clinical and agricultural production, the research and development of thiazole compounds has become one of the hot resea...

Claims

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Application Information

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IPC IPC(8): C07D417/06
CPCC07D417/06
Inventor 刘娥建方方刘泽民郑喜俊
Owner HENAN UNIV OF SCI & TECH
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