A kind of benzimidazole benzaldehyde acetal p-phenylenediamine bis-Schiff base and preparation method thereof

A technology of formaldehyde condensing p-phenylenediamine and benzimidazole, applied in the field of benzimidazole benzaldehyde condensing p-phenylenediamine bis-Schiff base and its preparation, can solve the problems such as no bis-Schiff base reported

Inactive Publication Date: 2017-01-04
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there have been many reports on the Schiff base compounds now, there are no reports about the bis-Schiff base of benzimidazole p-phenylenediamine

Method used

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  • A kind of benzimidazole benzaldehyde acetal p-phenylenediamine bis-Schiff base and preparation method thereof
  • A kind of benzimidazole benzaldehyde acetal p-phenylenediamine bis-Schiff base and preparation method thereof
  • A kind of benzimidazole benzaldehyde acetal p-phenylenediamine bis-Schiff base and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Weigh 1.180g (10mmol) of benzimidazole, weigh 1.240g (10mmol) of p-fluorobenzaldehyde and 1.380g (10mmol) of anhydrous potassium carbonate, dissolve in 30mL of dimethyl sulfoxide, add to the thermometer, A 50mL four-necked flask with a stirring device. Stir at a constant temperature at 90°C for 3 hours. After cooling to room temperature, extract with ethyl acetate for 3 times, wash with water, dry with anhydrous sodium sulfate, and spin-evaporate to obtain a yellow solid. Recrystallize with ethanol to obtain pure product. Dry in vacuum to obtain 4-benzene And imidazolyl benzaldehyde.

[0033] Weigh 0.222g (1mmol) of 4-benzimidazolylbenzaldehyde, weigh out 0.054g (0.500mmol) of p-phenylenediamine, dissolve it in 5mL of dimethyl sulfoxide, add to 10mL equipped with a thermometer and a stirring device Single-necked flask. Then add 0.120g (2mmol) of acetic acid to the above mixture, react at a constant temperature of 25°C for 10 hours, and distill under reduced pressure to r...

Embodiment 2

[0041] Weigh 3.260g (20mmol) of 5-nitrobenzimidazole, weigh 1.240g (10mmol) of p-fluorobenzaldehyde and 2.760g (20mmol) of anhydrous potassium carbonate, dissolve them in 35mL of dimethyl sulfoxide, and add to A 100 mL four-necked flask equipped with a thermometer and a stirring device. Stir at a constant temperature at 110°C for 2 hours. After cooling to room temperature, extract 3 times with ethyl acetate, wash with water, dry with anhydrous sodium sulfate, and spin-evaporate to obtain a yellow solid, which is recrystallized with ethanol to obtain a pure product, which is dried in vacuum to obtain 4-( 2-nitro-1-benzimidazolyl)benzaldehyde.

[0042] Weigh 0.267g (1mmol) of 4-(2-nitro-1-benzimidazolyl)benzaldehyde, weigh out 0.027g (0.25mmol) of p-phenylenediamine, dissolve it in 3mL of dimethyl sulfoxide, and add Into a 10-mL single-neck flask equipped with a thermometer and a stirring device. Then add 0.180g (3mmol) of acetic acid to the above mixture, react at a constant tem...

Embodiment 3

[0050] Weigh 2.960 g (20 mmol) of 2-methoxybenzimidazole, weigh 1.860 g (15 mmol) of p-fluorobenzaldehyde and 4.140 g (30 mmol) of anhydrous potassium carbonate, dissolve them in 40 mL of dimethyl sulfoxide, and add Into a 100mL four-neck flask equipped with a thermometer and a stirring device. Stir at a constant temperature at 120°C for 1 hour. After cooling to room temperature, extract 3 times with ethyl acetate, wash with water, dry with anhydrous sodium sulfate, and spin-evaporate to obtain a yellow solid, which is recrystallized with ethanol to obtain a pure product, which is dried in vacuum to obtain 4-( 2-Methoxy-1-benzimidazolyl)benzaldehyde.

[0051] Weigh out 0.756 g (3 mmol) of 4-(2-methoxy-1-benzimidazolyl)benzaldehyde, weigh out 0.130 g (1.250 mmol) of p-phenylenediamine, and dissolve it in 3 mL of dimethyl sulfoxide. Add to a 10-mL single-neck flask equipped with a thermometer and a stirring device. Then add 0.720g (12mmol) of acetic acid to the above mixture, rea...

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Abstract

The invention relates to a benzimidazole benzaldehyde p-phenylenediamine bis-Schiff base and a preparation method thereof. First, benzimidazole and its derivatives and p-fluorobenzaldehyde are used as raw materials to prepare 4-benzimidazolyl benzaldehyde or benzimidazole derivative benzaldehyde, and then utilize it and p-phenylenediamine through the formation of aldehyde group and primary amine Condensation reactions yielded a series of bis-Schiff bases with larger conjugated structures. The process has low synthesis cost, high yield, easy control of reaction conditions and simple product purification. The novel compound of the invention has good fluorescence performance and is selective to metal ions, and can be applied in the field of materials or sensors.

Description

Technical field [0001] The present invention relates to a benzimidazole benzaldehyde condensed p-phenylenediamine bis-Schiff base and a preparation method thereof. The compound has a conjugated and rigid planar structure, exhibits good fluorescence performance, and contains C=N functional groups. Coordination with metal ions, with good ion selectivity. Background technique [0002] Benzimidazole is a heterocyclic compound containing two nitrogen atoms. It has a wide range of biological activities, such as anti-cancer and anti-fungal. It can be used as a raw material or intermediate for synthetic drugs, and it can also be used as a new curing agent and catalyst for epoxy resin. And some metal surface treatment agents and chelating agents. In addition, the benzimidazole molecule is composed of a nitrogen-containing five-membered heterocycle and a benzene ring in parallel. Because of the structure of the benzene ring and the azole ring, it has rich energy levels. As a nitrogen-cont...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/06C07D235/24C07D235/26C09K11/06G01N21/64
Inventor 段洪东徐婷卜娟
Owner QILU UNIV OF TECH
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