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Method of rapidly preparing rhodamine dye with a plurality of active functional groups under mild condition

A technology of functional groups and conditions, applied in the direction of benzoxanthamine/xanthone/thioxanthone/selenoxanthone/tellurium xanthone dyes, organic chemistry, etc., can solve the price of functional rhodamine Expensive, difficult separation, application limitations and other problems, to achieve the effect of cheap catalyst, simple separation and easy operation

Inactive Publication Date: 2017-07-14
苏州高德瑞仪器有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods obtain two isomers that are extremely difficult to separate, and need to be separated by preparative high-pressure liquid chromatography in a small amount and many times. Therefore, functional rhodamine is often extremely expensive and its application is greatly limited.

Method used

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  • Method of rapidly preparing rhodamine dye with a plurality of active functional groups under mild condition
  • Method of rapidly preparing rhodamine dye with a plurality of active functional groups under mild condition
  • Method of rapidly preparing rhodamine dye with a plurality of active functional groups under mild condition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043]

[0044] Put p-bromobenzaldehyde (1mmol, 185mg) and 3-hydroxy-N, N-diethylaniline (2mmol, 330mg) in a 25mL two-necked bottle, add p-toluenesulfonic acid (0.15mmol, 26mg), Add 15 mL of glacial acetic acid. Reaction at 70 degrees for 7 hours, at this time the solution turned dark purple, most of the acetic acid was removed under reduced pressure, and saturated NaHCO was added 3 , produce a lot of bubbles, until the purple precipitate is completely precipitated, filter out the purple precipitate, and dissolve it in 30mL of CH 2 Cl 2 Chlorobenzoquinone (0.5mmol, 122mg) was added to the solution, the color of the solution became darker, reacted for 2h, and CH was removed under reduced pressure 2 Cl 2 , separated on a silica gel column to obtain bright purple crystals. The yield was 45%. 1 H NMR (400MHz, CDCl 3 ):δ=7.79(d,2H,J=8.0Hz),7.32-7.28(m,4H),7.01-6.98(m,2H),6.86(s,2H),3.72-3.66(t,8H), 1.37-1.33ppm(m,12H). 13 C NMR (100MHz, CDCl 3 ): δ=158.1, 157.8, 131.2, ...

Embodiment 2

[0046]

[0047] Put m-bromobenzaldehyde (1mmol, 185mg) and -hydroxy-N, N-diethylaniline (2mmol, 330mg) in a 25mL two-neck flask, add p-toluenesulfonic acid (0.15mmol, 26mg), add 15 mL of glacial acetic acid. Reaction at 70 degrees for 7 hours, at this time the solution turned dark purple, most of the acetic acid was removed under reduced pressure, and saturated NaHCO was added 3 , produce a lot of bubbles, until the purple precipitate is completely precipitated, filter out the purple precipitate, and dissolve it in 30mL of CH 2 Cl 2 Chlorobenzoquinone (0.5mmol, 122mg) was added to the solution, the color of the solution became darker, reacted for 2h, and CH was removed under reduced pressure 2 Cl 2 , separated on a silica gel column to obtain bright purple crystals. The yield was 43%. 1 H NMR (400MHz, CDCl 3 ):δ=7.78(d,1H,J=7.8Hz),7.55-7.51(t,2H),7.36(d,1H,J=7.6Hz),7.30(s,1H),7.05(s,1H) ,6.97(d,2H,J=12.0Hz),6.86(s,2H),3.67-3.66(m,8H),1.35-1.31ppm(t,12H). 13 C NMR (1...

Embodiment 3

[0049]

[0050] Put p-fluorobenzaldehyde (1mmol, 124mg) and 3-hydroxy-N, N-diethylaniline (2mmol, 330mg) in a 25mL two-necked bottle, add p-toluenesulfonic acid (0.15mmol, 26mg), Add 15 mL of glacial acetic acid. Reaction at 70 degrees for 7 hours, at this time the solution turned dark purple, most of the acetic acid was removed under reduced pressure, and saturated NaHCO was added 3 , produce a lot of bubbles, until the purple precipitate is completely precipitated, filter out the purple precipitate, and dissolve it in 30mL of CH 2 Cl 2 Chlorobenzoquinone (0.5mmol, 122mg) was added to the solution, the color of the solution became darker, reacted for 2h, and CH was removed under reduced pressure 2 Cl 2 , separated on a silica gel column to obtain bright purple crystals with a yield of 41%. 1 H NMR (400MHz, CDCl 3 ):δ=7.38(d,2H,J=4.0Hz),7.33-7.31(m,4H),6.98(d,2H,J=8.0Hz),6.83(s,2H),3.67-3.65(m, 8H),1.34-1.23ppm(m,12H). 13 C NMR (100MHz, CDCl 3 ): δ=158.1, 155.7, 131...

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Abstract

The invention relates to a method of rapidly preparing a rhodamine dye with a plurality of active functional groups under the mild condition and belongs to the technical field of fine chemicals. The method is used for synthesizing rhodamine with specific functional groups by carrying out simple chemical modification on raw materials and has an important guiding significance to derivatization of the rhodamine dye. Compared with the commercially available rhodamine dye, the rhodamine dye has multiple active functional groups and is beneficial to derivatization of the rhodamine dye. By adopting the method, the rhodamine dye with the specific functional groups can be synthesized by 6-7h only without protection of inert gas, so that the synthesis time of the rhodamine dye is greatly saved, the purpose of the rhodamine dye is expanded, the synthesis yield of the rhodamine dye is greatly increased, and the separation difficulty of the rhodamine dye is prevented. Through the advantages, the purpose of the rhodamine dye is expanded, so that the rhodamine dye can be fully developed in the fields of biolabeling, cell imaging, fluorescent probes and the like.

Description

technical field [0001] The invention relates to a method for rapidly preparing rhodamine dyes with multiple active functional groups under mild conditions, which belongs to the technical field of fine chemicals. Background technique [0002] Rhodamine dyes are widely used in social production activities. For example, biomarkers, cell imaging, fluorescent probes, etc. Rhodamine is used to design molecular fluorescent probes, which can effectively detect heavy metal ions and harmful anions, and can also be used for cell imaging, biomarkers, etc. Rhodamine presents a great challenge. The synthesis of functional rhodamine by traditional methods often requires many steps, and there is also a complicated purification process. This makes the excellent photochemical and photophysical properties of rhodamine are greatly limited. Therefore, there is an urgent need for a convenient, fast and efficient method for synthesizing functional rhodamine. [0003] The traditional method of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/82C09B11/28
CPCC07D311/82C09B11/28
Inventor 赵建章黄玲
Owner 苏州高德瑞仪器有限公司
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