2-(4-trifluoromethylphenyl)-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole preparation method

A technology of trifluoromethyl phenyl, trifluoromethyl benzoic acid, applied in 2-(4-trifluoromethylphenyl)-6-ferrocenyl-imidazo[2,1-b]- The field of preparation of 1,3,4-thiadiazole can solve the problems of low reaction efficiency and long reaction time, and achieve the effect of improving reaction efficiency and shortening reaction time.

Inactive Publication Date: 2017-12-22
ZHANGJIAGANG MAOAN TRADING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The disadvantages of traditional methods are: long reaction time and low reaction efficiency

Method used

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  • 2-(4-trifluoromethylphenyl)-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole preparation method
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  • 2-(4-trifluoromethylphenyl)-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole preparation method

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Embodiment 1

[0023] Synthesis of 2-(4-trifluoromethylphenyl)-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole

[0024] chemical reaction formula

[0025]

[0026] Synthetic steps:

[0027] (1), mix solid thiosemicarbazide, 4-trifluoromethylbenzoic acid and hydrobromic acid, turn on the oil bath to heat and stir, wherein the mass ratio of solid thiosemicarbazide to 4-trifluoromethylbenzoic acid It is 1:2.4, and the mass fraction of hydrobromic acid is 50%; Heat up to 105 ℃ and keep warm for 4.7 hours, cool to room temperature after completion of the reaction; adjust the pH to 8-9 with 40% sodium hydroxide solution under stirring in an ice-water bath; react The solid was precipitated from the liquid, and it was allowed to stand in an ice-water bath for 30 minutes to fully analyze; it was filtered under reduced pressure, and the filter cake was collected and dried to obtain the crude product; the crude product was recrystallized with 30% ethanol aqueous solution, and dried to obtain 2-amino-...

Embodiment 2

[0036] Synthesis steps of 2-(4-trifluoromethylphenyl)-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole:

[0037] (1), mix solid thiosemicarbazide, 4-trifluoromethylbenzoic acid and hydrobromic acid, turn on the oil bath to heat and stir, wherein the mass ratio of solid thiosemicarbazide to 4-trifluoromethylbenzoic acid It is 1:2.51, and the mass fraction of hydrobromic acid is 50%; Heating up to 104 ℃ of insulations for 4.6 hours, cooling to room temperature after completion of the reaction; adjusting pH to 8~9 with 39% sodium hydroxide solution under ice-water bath stirring; Reaction The solid was precipitated from the liquid, and it was allowed to stand in an ice-water bath for 30 minutes to fully analyze; it was filtered under reduced pressure, and the filter cake was collected and dried to obtain the crude product; the crude product was recrystallized with 30% ethanol aqueous solution, and dried to obtain 2-amino-5-(4-trifluoro Methylphenyl)-1,3,4-thiadiazole;

[0038] (2) S...

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Abstract

The present invention discloses a 2-(4-trifluoromethylphenyl)-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole preparation method, which comprises: carrying out stirring mixing on 2-amino-5-(4-trifluoromethylphenyl)-1,3,4-thiadiazole, alpha-bromo-acetylferrocene and ethanol; placing the mixed solution in a microwave oven, and carrying out microwave irradiation; after the alpha-bromo-acetylferrocene completely reacts, carrying out a microwave reaction; adding water to the reaction solution, and adjusting the pH value of the reaction solution to 7-8 with a saturated sodium carbonate solution; carrying out suction filtration, washing the filter cake with water, and drying to obtain a crude product; and re-crystallizing with DMF to obtain the target product. According to the present invention, the microwave-assisted synthesis reaction is used so as to substantially shorten the reaction time and improve the reaction efficiency.

Description

technical field [0001] The application relates to a preparation method of 2-(4-trifluoromethylphenyl)-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole. Background technique [0002] Imidazo[2,1-b]-1,3,4-thiadiazole is obtained from the ring-forming reaction of 1,3,4-thiadiazole compounds and α-halogenated ketones. [0003] The traditional preparation method is that 1,3,4-thiadiazole and α-haloketone are refluxed in alcohol solvent for several hours to generate hydrobromide intermediate, and then add lye to undergo intramolecular ring closure reaction to obtain imidazo[2 ,1-b]-1,3,4-thiadiazole. [0004] The disadvantages of the traditional method are: long reaction time and low reaction efficiency. Contents of the invention [0005] The object of the present invention is to provide a kind of preparation method of 2-(4-trifluoromethylphenyl)-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole , to overcome the deficiencies in the prior art. [0006] To achieve the above object, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02
CPCC07F17/02
Inventor 徐靖
Owner ZHANGJIAGANG MAOAN TRADING
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