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

A nitrophenyl, ferrocenyl technology, applied in 2-(4-nitrophenyl)-6-ferrocenyl-imidazo[2,1-b]-1,3,4- In the field of thiadiazole preparation, it can solve the problems of long reaction time and low reaction efficiency, and achieve the effect of shortening the reaction time and improving the reaction efficiency

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Synthesis of 2-(4-nitrophenyl)-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole

[0023] chemical reaction formula

[0024]

[0025] Synthetic steps:

[0026] (1), mix solid thiosemicarbazide, nitrobenzoic acid and hydrobromic acid, turn on the oil bath to heat and stir, wherein the mass ratio of solid thiosemicarbazide and nitrobenzoic acid is 1:2.1, hydrobromic acid The mass fraction is 50%; the temperature is raised to 105 ℃ for 4.7 hours, and the reaction is cooled to room temperature after the completion of the reaction; the pH is adjusted to 8-9 with 40% sodium hydroxide solution under stirring in an ice-water bath; Set aside for 30 minutes to fully separate out; 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-(4-nitrophenyl)-1,3, 4-thiadiazole;

[0027] (2) Stir and mix 2-amino-5-(4-nitrophenyl)-1,3,4-thiadiazole, α-bromo-a...

Embodiment 2

[0035] Synthesis steps of 2-(4-nitrophenyl)-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole:

[0036] (1), mix solid thiosemicarbazide, nitrobenzoic acid and hydrobromic acid, turn on the oil bath to heat and stir, wherein the mass ratio of solid thiosemicarbazide and nitrobenzoic acid is 1:2.2, hydrobromic acid The mass fraction is 50%; the temperature is raised to 104 ℃ for 4.6 hours, and the reaction is cooled to room temperature after the completion of the reaction; the pH is adjusted to 8-9 with 39% sodium hydroxide solution under stirring in an ice-water bath; Set aside for 30 minutes to fully separate out; 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-(4-nitrophenyl)-1,3, 4-thiadiazole;

[0037] (2) Stir and mix 2-amino-5-(4-nitrophenyl)-1,3,4-thiadiazole, α-bromo-acetylferrocene and ethanol, wherein 2-amino-5 The molar ratio of -(...

Embodiment 3

[0045] Synthesis steps of 2-(4-nitrophenyl)-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole:

[0046] (1), mix solid thiosemicarbazide, nitrobenzoic acid and hydrobromic acid, turn on the oil bath to heat and stir, wherein the mass ratio of solid thiosemicarbazide and nitrobenzoic acid is 1:2, hydrobromic acid The mass fraction of the solution was 50%; the temperature was raised to 105°C for 4.5 hours, and cooled to room temperature after the reaction was completed; the pH was adjusted to 8-9 with 40% sodium hydroxide solution under stirring in an ice-water bath; Set aside for 28 minutes to fully separate out; 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-(4-nitrophenyl)-1,3, 4-thiadiazole;

[0047] (2) Stir and mix 2-amino-5-(4-nitrophenyl)-1,3,4-thiadiazole, α-bromo-acetylferrocene and ethanol, wherein 2-amino-5 The molar ratio of -(4-n...

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Abstract

The present invention discloses a 2-(4-nitrophenyl)-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole preparation method, which comprises: carrying out stirring mixing on 2-amino-5-(4-nitrophenyl)-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-nitrophenyl)-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-nitrophenyl)-6-ferrocenyl-imidazo[2,1-b]-1,3,4-thiadiazole, with Overcome the deficiencies in the prior art. [0006] To achieve the above object, the present inventi...

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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