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Process for synthesizing polymethin cyanine compound containing indole ring

The technology of a cyanine compound and a synthesis method, which is applied in the field of preparation of functional dyes, can solve the problems of difficult recycling, increased production costs, and easy hydrolysis of acetic anhydride, and achieves low production costs, avoids irritation, and has stable chemical properties Effect

Inactive Publication Date: 2004-09-29
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The above-mentioned known synthetic method adopts acetic anhydride as the reaction medium, and there are obvious defects that acetic anhydride is easy to hydrolyze, recycling is difficult, and increases production cost.

Method used

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  • Process for synthesizing polymethin cyanine compound containing indole ring
  • Process for synthesizing polymethin cyanine compound containing indole ring
  • Process for synthesizing polymethin cyanine compound containing indole ring

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 15ml of DMF or DMSO, 2ml of pyridine, 2.0g of 5-anilinopentadienal aniline hydrochloride, N-n-butyl-2,3,3-trimethylindoline perchlorate into a 100ml four-necked bottle Salt 5.0g, heated to 70°C with stirring, reacted for 3h, diluted with water, cooled to 20°C, filtered, washed with water, recrystallized from methanol, dried at 80°C to obtain heptamethine compound 1,1' containing indole ring -Di-n-butyl-3,3,3',3'-tetramethylindole tricarbocyanine perchlorate 3.0g.

Embodiment 2

[0026] Add 15ml of DMF, 4g of sodium acetate, 2.0g of 5-anilinopentadienal aniline hydrochloride, and N-n-butyl-2,3,3-trimethylindoline perchlorate into a 100ml four-necked bottle 5.0g, heated to 90°C with stirring, reacted for 2h, diluted with water, cooled to 20°C, filtered, washed with water, recrystallized from methanol, dried at 80°C to obtain heptamethine compound 1,1'-di n-Butyl-3,3,3',3'-tetramethylindole tricarbocyanine perchlorate 3.1g.

Embodiment 3

[0028] Add 15ml of DMF, 2.5ml of piperidine, 2.0g of 3-anilinopropenal aniline hydrochloride, N-n-butyl-2,3,3-trimethyl-4,5-benzoindole into a 100ml four-necked bottle Indoline perchlorate 6.0g, heated to 80°C with stirring, reacted for 2h, diluted with water, cooled to 15°C, filtered, washed with water, recrystallized with ethanol, dried at 80°C to obtain pentamethylcyanine compounds containing indole rings 1,1'-Di-n-butyl-3,3,3',3'-tetramethyl-4,5-benzoindole dicarbocyanine perchlorate 3.8g.

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Abstract

The present invention relates to functional dye, and is especially the process of synthesizing polymethin cyanine compound containing indole ring. The present invention features that by using ketone and / or dipolar solvent as reaction and alkali catalyst, heterocyclic compound containing active methyl is made to react with condensated 5-anilino pentadiene aldehyde-aniline hydrochloride compound to obtain heptamethin cyanine compound containing indole ring or with 3-anilino acraldehyde-aniline hydrochloride compound to obtain pentamethin cyanine compound containing indole ring. Owing to the stable chemical property of the ketone and / or dipolar solvent, they may be recovered in conventional distillation method, resulting in low production cost and no excitability.

Description

technical field [0001] The invention belongs to the preparation method of functional dyes, in particular to the synthesis method of polymethine compounds containing indole rings. Background technique [0002] Containing the polymethine cyanine compound of indole ring, its structural formula is as follows: [0003] [0004] where R 1 is n-butyl, R 2 for hydrogen. Z is ClO 4 - , I - . Where n=2 is a pentamethine compound, and n=3 is a heptamethine compound. [0005] It can be seen from the above structural formula that polymethine cyanine compounds containing indole rings all have polymethine chains, namely -(CH=CH) n -CH=, the difference is the structure of the heterocyclic part at the two ends of the chain and the substituents it carries. [0006] For the polymethine cyanine compound containing indole ring, the known synthetic method usually adopts the indole compound and 5-anilino pentadienal aniline hydrochloride with active methyl group in the 2 position, in a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/16
Inventor 刘福德雷英杰韩宝成邵仕香谢秀荣
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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