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Preparation method of fluorescein probe with specific selectivity

A selectivity and fluorescein technology, applied in the field of preparation of fluorescein probes, can solve problems affecting the conversion rate and yield of 5-fluorescein isothiocyanate, achieve mild conditions, easy operation, improve conversion rate and Yield effect

Active Publication Date: 2021-05-28
TIANJIN QUANHECHENG TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the above reaction, due to the different positions of the nitro group after the reaction, the mixed intermediate product of the two isomers has to be separated and purified for the next step of the reaction, which greatly affects the fluorescein 5-isothiocyanate. Conversion and Yield

Method used

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  • Preparation method of fluorescein probe with specific selectivity
  • Preparation method of fluorescein probe with specific selectivity
  • Preparation method of fluorescein probe with specific selectivity

Examples

Experimental program
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Effect test

Embodiment 1

[0041] The specific and selective fluorescein probe 5-fluorescein isothiocyanate is prepared according to the preparation method of the present application:

[0042](1) under the continuous stirring of 40rpm, the 4-nitrophthalic anhydride of 100g, the resorcinol of 118g, the nitrocyclohexane of 55g and the anhydrous cobalt chloride of 20g are mixed, Heat and melt at 125°C, add 100g of zinc chloride to it, react at 145°C for 4 hours, then add 1000mL of hydrochloric acid with a concentration of 0.75mol / L, heat and reflux for 40 minutes, filter, and filter the cake with 55°C Washed with water until neutral, dried at 85° C. for 2.5 hours to obtain 192.59 g of product (which contained 91.52% of 5-nitrofluorescein and 2.37% of 6-nitrofluorescein);

[0043] (2) Na 2 S and Na 2 SO 3 Dissolve in water to prepare reducing solutions with concentrations of 0.80 g / mL and 0.15 g / mL respectively, mix the product of step (1) with 1160 mL of the reducing solution, react at 75 ° C for 8.5 ho...

Embodiment 2

[0046] The specific and selective fluorescein probe 5-fluorescein isothiocyanate is prepared according to the preparation method of the present application:

[0047] (1) under the continuous stirring of 50rpm, the 4-nitrophthalic anhydride of 100g, the resorcinol of 120g, the nitrocyclohexane of 52g and the anhydrous cobalt chloride of 27g are mixed, Heat and melt at 115°C, add 100g of zinc chloride to it, react at 135°C for 5 hours, then add 1200mL of hydrochloric acid with a concentration of 0.75mol / L, heat and reflux for 45 minutes, filter, and filter the cake with 50°C Washed with water to neutrality, dried at 80° C. for 2 hours to obtain 193.45 g of product (which contained 92.38% of 5-nitrofluorescein and 2.15% of 6-nitrofluorescein);

[0048] (2) Na 2 S and Na 2 SO 3 Dissolve in water to prepare reducing solutions with concentrations of 0.60 g / mL and 0.20 g / mL respectively, mix the product obtained in step (1) with 1350 mL of the reducing solution, react at 80 ° C fo...

Embodiment 3

[0051] The specific and selective fluorescein probe 5-fluorescein isothiocyanate is prepared according to the preparation method of the present application:

[0052] (1) under the continuous stirring of 60rpm, the 4-nitrophthalic anhydride of 100g, the resorcinol of 118g, the nitrocyclohexane of 50g and the anhydrous cobalt chloride of 25g are mixed, Heat and melt at 120°C, add 110g of zinc chloride to it, react at 140°C for 4.5 hours, then add 1000mL of hydrochloric acid with a concentration of 0.7mol / L, heat and reflux for 30 minutes, filter, and filter the cake with 55°C Washed with water to neutrality, dried at 90° C. for 3 hours to obtain 193.04 g of product (which contained 90.89% of 5-nitrofluorescein and 2.89% of 6-nitrofluorescein);

[0053] (2) Na 2 S and Na 2 SO 3 Dissolve in water to prepare reducing solutions with concentrations of 0.80g / mL and 0.20g / mL respectively, mix the product obtained in step (1) with 1160mL of the reducing solution, react at 70°C for 9 ...

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Abstract

The invention relates to the field of preparation of fluorescein probes with specific selectivity, and particularly discloses a preparation method of a fluorescein probe with specific selectivity. The method comprises the following steps: (1) mixing 4-nitrophthalic anhydride, resorcinol, nitrocyclohexane and anhydrous cobalt chloride, conducting heating and melting, adding zinc chloride, conducting reacting, then adding hydrochloric acid for reflux, and conducting filtering, washing and drying; (2) mixing a reducing solution containing Na2S and Na2SO3 with a product obtained in the step (1), conducting reacting, then dropwise adding glacial acetic acid until complete precipitation, and conducting filtering, washing and drying; and (3) mixing a mixed solvent containing methanol and triethylamine with a product obtained in the step (2), dropwise adding CS2, conducting reacting, dropwise adding a copper chloride aqueous solution, continuing reacting after dropwise adding, adjusting the pH value of the system to 1-2 by using hydrochloric acid, and carrying out reduced pressure distillation, washing, drying and column chromatography purification. According to the method, the conversion rate and the yield of the 5-fluorescein isothiocyanate are greatly improved.

Description

technical field [0001] The present application relates to the field of preparation of fluorescein probes with specific selectivity, more specifically, relates to a preparation method of fluorescein probes with specific selectivity. Background technique [0002] Fluorescein probes are a class of probes that use fluorescein and its derivatives to interact with target molecules to detect target molecules by changing the fluorescence spectrum (including fluorescence intensity, fluorescence excitation and emission wavelengths, fluorescence lifetime, and fluorescence polarization / anisotropy, etc.). The organic fluorescent functional dye for detection has the advantages of extremely low detection limit and high sensitivity, and is especially suitable for specific detection of certain low-content substances, especially biological materials. [0003] 5-Fluorescein isothiocyanate (5-FITC) is one of the most widely used fluorescent labeling probes. Its maximum absorption wavelength is ...

Claims

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Application Information

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IPC IPC(8): C07D493/10C09K11/06
CPCC07D493/10C09K11/06C09K2211/1088
Inventor 宋艳民陈勇张超
Owner TIANJIN QUANHECHENG TECH
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