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Ferrocenyl-containing thiadiazolyl Schiff base and preparation method thereof

A technology based on thiadiazolyl and ferrocene, which is applied in the field of Schiff base containing ferrocenyl thiadiazolyl and its preparation, can solve the problems of long reflux time, high reaction temperature, low yield and the like, and achieves the reaction The effect of short time, simple operation and high yield

Active Publication Date: 2019-10-01
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The traditional Schiff base synthesis method uses Lewis acid as a catalyst and absolute ethanol as a solvent. The reflux time is long, the reaction temperature is high, the yield is low, and it is not environmentally friendly. Therefore, a simple operation, high yield, green environmental protection, and low cost have been developed. The preparation method of Schiff base containing ferrocenyl thiadiazolyl has certain significance

Method used

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  • Ferrocenyl-containing thiadiazolyl Schiff base and preparation method thereof
  • Ferrocenyl-containing thiadiazolyl Schiff base and preparation method thereof
  • Ferrocenyl-containing thiadiazolyl Schiff base and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 Preparation of acetyl ferrocene 2-amino-1,3,4-thiadiazole Schiff base:

[0038] Add 1.4g (10mmol) of choline chloride in a dry three-necked flask, 1.92 (20mmol) of methanesulfonic acid, stir at room temperature to obtain a deep eutectic solvent, then add 0.23g (1mmol) acetyl ferrocene, 0.12 g (1.2 mmol) 2-amino-1,3,4-thiadiazole was reacted in a water bath at 40°C, and monitored by TLC until the reaction was complete. After the reaction, the reaction solution was poured into water, extracted with dichloromethane, and the solvent was distilled off to obtain a crude product, and the water phase was recovered to obtain a deep eutectic solvent again. The crude product was recrystallized from absolute ethanol to obtain the pure product containing ferrocenyl thiadiazolyl Schiff base. The yield is 94.2%, and the melting point is 148-149°C.

[0039] IR(KBr) ν: 3301cm -1 ,3089cm -1 ( ν 二茂铁C-H ); 2923cm -1 ( ν CH3 ); 1375cm -1 ( ν CH3 ) ;1604cm -1 ( ν...

Embodiment 2

[0041] Example 2 Preparation of acetyl ferrocene 2-amino-5-methyl-1,3,4-thiadiazole Schiff base

[0042] Add 1.4g (10mmol) of choline chloride in a dry three-necked flask, 1.92 (20mmol) of methanesulfonic acid, stir at room temperature to obtain a deep eutectic solvent, then add 0.23g (1mmol) acetyl ferrocene, 0.14 g (1.2 mmol) 2-amino-5-methyl-1,3,4-thiadiazole was reacted in a water bath at 40°C, and monitored by TLC until the reaction was complete. After the reaction, the reaction solution was poured into water, extracted with dichloromethane, and the solvent was distilled off to obtain a crude product, and the water phase was recovered to obtain a deep eutectic solvent again. The crude product was recrystallized from absolute ethanol to obtain the pure product containing ferrocenyl thiadiazolyl Schiff base. The yield is 90.3%, and the melting point is 150-152°C.

[0043] IR(KBr) ν: 3426cm -1 ( ν 二茂铁C-H ); 2925cm -1 ( ν CH3 ); 1377cm -1 ( ν CH3 ) ; 1605cm ...

Embodiment 3

[0045] Example 3 Preparation of acetyl ferrocene 2-amino-5-ethyl-1,3,4-thiadiazole Schiff base

[0046] Add 1.4g (10mmol) of choline chloride in a dry three-necked flask, 1.92 (20mmol) of methanesulfonic acid, stir at room temperature to obtain a deep eutectic solvent, then add 0.23g (1mmol) acetyl ferrocene, 0.15 g (1.2 mmol) 2-amino-5-ethyl-1,3,4-thiadiazole was reacted in a water bath at 40°C, and monitored by TLC until the reaction was complete. After the reaction, the reaction solution was poured into water, extracted with dichloromethane, and the solvent was distilled off to obtain a crude product, and the water phase was recovered to obtain a deep eutectic solvent again. The crude product was recrystallized from absolute ethanol to obtain the pure product containing ferrocenyl thiadiazolyl Schiff base. The yield is 91.7%, and the melting point is 145-146°C.

[0047] IR(KBr) ν: 3291cm -1 ,3114cm -1 ( ν 二茂铁C-H ); 2928cm -1 ( ν CH3 ); 1742cm -1 , 1380cm -1 (...

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Abstract

A mol of choline chloride and B mol of methanesulfonic acid are added into a dry three-necked flask, stirring is executed at room temperature to obtain a eutectic solvent, and then C mol of acetylferrocene and D mol of 2-amino-5-substituted-1,3,4-thiadiazole are added, reaction is executed in a water bath of 40 DEG C, and TLC monitoring is executed until the reaction is completed; after the reaction is completed, the reaction liquid is poured into water, extraction is executed with dichloromethane, the solvent is evaporated to obtain a crude product, and a water phase is recovered to obtain the eutectic solvent again; the crude product is recrystallized by absolute ethyl alcohol to obtain the pure ferrocenyl-containing thiadiazolyl Schiff base. The method is simple in operation, high in yield, high in product purity, short in reaction time and simple in post-treatment, the eutectic solvent is recyclable, environmentally friendly and low in cost, and the method has the important significance in synthesis and development of the compounds.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a ferrocenyl-thiadiazolyl-containing Schiff base and a preparation method thereof. Background technique [0002] Schiff base has strong physiological activity and anti-fungal activity, and can be used as antibacterial, anti-cancer, anti-tumor, anti-tuberculosis and other drugs; and the complex formed by Schiff base compound and metal also has a good oxygen-carrying capacity. Activity; at the same time, Schiff base and its complexes also have good catalytic activity, and can be used as catalysts in asymmetric synthesis and polymer synthesis. The simultaneous introduction of ferrocene and heterocyclic amines into compounds to synthesize ferrocenyl-thiadiazolyl-containing Schiff bases will surely become a new hotspot in the future research on Schiff bases. [0003] The traditional Schiff base synthesis method uses Lewis acid as a catalyst and absolute ethanol as a solvent. The ref...

Claims

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Application Information

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IPC IPC(8): C07F17/02
CPCC07F17/02
Inventor 刘玉婷杨岚尹大伟党阳邹倩李洁孙嘉希
Owner SHAANXI UNIV OF SCI & TECH
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