2-n-propyl-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole preparation method

A ferrocene-based and acetyl-ferrocene technology, applied in chemical instruments and methods, metallocenes, organic chemistry, etc., can solve the problems of low reaction efficiency and long reaction time, so as to improve reaction efficiency and shorten reaction time Effect

Inactive Publication Date: 2017-12-22
ZHANGJIAGANG MAOAN TRADING
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  • 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-n-propyl-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis method of 2-n-propyl-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole

[0030] chemical reaction formula

[0031]

[0032] Synthetic steps:

[0033] (1), mix solid thiosemicarbazide, n-butyric acid and hydrobromic acid, turn on the oil bath to heat and stir, wherein the mass ratio of solid thiosemicarbazide and n-butyric acid is 1:1.15, the mass fraction of hydrobromic acid 50%; heat up to 105°C and keep warm for 4.7 hours, cool to room temperature after the reaction is complete; adjust the pH to 8-9 with 40% sodium hydroxide solution under stirring in an ice-water bath; solids precipitate out of the reaction solution, and stand in an ice-water bath for 30 minutes Fully analyze; filter under reduced pressure, collect the filter cake and dry to obtain the crude product; recrystallize the crude product with 30% ethanol aqueous solution, and dry to obtain 2-amino-5-n-propyl-1,3,4-thiadiazole;

[0034] (2) Stir and mix 2-amino-5-n-propyl-1,3,4-thiadiazole, α-bro...

Embodiment 2

[0042] Synthesis steps of 2-n-propyl-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole:

[0043] (1), mix solid thiosemicarbazide, n-butyric acid and hydrobromic acid, turn on the oil bath to heat and stir, wherein the mass ratio of solid thiosemicarbazide and n-butyric acid is 1:1.25, the mass fraction of hydrobromic acid 50%; heat up to 104°C and keep warm for 4.6 hours, cool to room temperature after the reaction is complete; adjust the pH to 8-9 with 39% sodium hydroxide solution under stirring in an ice-water bath; solids precipitate out of the reaction solution, and stand in an ice-water bath for 30 minutes Fully analyze; filter under reduced pressure, collect the filter cake and dry to obtain the crude product; recrystallize the crude product with 30% ethanol aqueous solution, and dry to obtain 2-amino-5-n-propyl-1,3,4-thiadiazole;

[0044] (2) Stir and mix 2-amino-5-n-propyl-1,3,4-thiadiazole, α-bromo-acetylferrocene and ethanol, wherein 2-amino-5-n-propyl- The molar rati...

Embodiment 3

[0052] Synthesis steps of 2-n-propyl-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole:

[0053] (1), mix solid thiosemicarbazide, n-butyric acid and hydrobromic acid, turn on the oil bath to heat and stir, wherein the mass ratio of solid thiosemicarbazide and n-butyric acid is 1:1.2, and the mass fraction of hydrobromic acid 50%; heat up to 105°C and keep warm for 4.5 hours, cool to room temperature after the reaction is complete; adjust the pH to 8-9 with 40% sodium hydroxide solution under stirring in an ice-water bath; solids precipitate out of the reaction solution, and stand in an ice-water bath for 28 minutes Fully analyze; filter under reduced pressure, collect the filter cake and dry to obtain the crude product; recrystallize the crude product with 28% ethanol aqueous solution, and dry to obtain 2-amino-5-n-propyl-1,3,4-thiadiazole;

[0054] (2) Stir and mix 2-amino-5-n-propyl-1,3,4-thiadiazole, α-bromo-acetylferrocene and ethanol, wherein 2-amino-5-n-propyl- The molar r...

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Abstract

The present invention discloses a 2-n-propyl-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole preparation method, which comprises: carrying out stirring mixing on 2-amino-5-n-propyl-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-n-propyl-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-n-propyl group-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole, to overcome the prior art lack of. [0006] To achieve the above object, the present invention provides the follow...

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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