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A kind of preparation method of fluorescein probe with specific selectivity

A selective, fluorescein technology, applied in the field of preparation of fluorescein probes, can solve the problems affecting the conversion rate and yield of fluorescein 5-isothiocyanate, and achieve mild conditions, simple operation, improved conversion rate and high efficiency. The effect of yield

Active Publication Date: 2022-06-07
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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  • A kind of preparation method of fluorescein probe with specific selectivity
  • A kind of preparation method of fluorescein probe with specific selectivity
  • A kind of preparation method of fluorescein probe with specific selectivity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0042](1) under the continuous stirring that stirring speed is 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 100 g of zinc chloride to it, react at 145°C for 4 hours, then add 1000 mL of hydrochloric acid with a concentration of 0.75 mol / L, heat under reflux for 40 minutes, filter, and filter the filter cake with 55°C Washed with water until neutral, dried at 85°C for 2.5 hours to obtain 192.59 g of product (containing 91.52% 5-nitrofluorescein and 2.37% 6-nitrofluorescein);

[0043] (2) The 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 result of step (1) with 1160 mL of the reducing sol...

Embodiment 2

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

[0047] (1) under the continuous stirring that stirring speed is 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 100 g of zinc chloride to it, react at 135°C for 5 hours, then add 1200 mL of hydrochloric acid with a concentration of 0.75 mol / L, heat under reflux for 45 minutes, filter, and filter cake with 50°C Washed with water until neutral, and dried at 80°C for 2 hours to obtain 193.45 g of product (containing 92.38% 5-nitrofluorescein and 2.15% 6-nitrofluorescein);

[0048] (2) The 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 resultant of step (1) with 1350 mL of the reducing solution...

Embodiment 3

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

[0052] (1) under the continuous stirring that stirring speed is 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 110 g of zinc chloride to it, react at 140°C for 4.5 hours, then add 1000 mL of hydrochloric acid with a concentration of 0.7 mol / L, heat under reflux for 30 minutes, filter, and filter the filter cake with 55°C Washed with water until neutral, dried at 90°C for 3 hours to obtain 193.04 g of product (containing 90.89% 5-nitrofluorescein and 2.89% 6-nitrofluorescein);

[0053] (2) The Na 2 S and Na 2 SO 3 Dissolve in water to prepare reducing solutions with concentrations of 0.80 g / mL and 0.20 g / mL, respectively, mix the result of step (1) with 1160 mL of the reducing sol...

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Abstract

The application relates to the field of preparation of fluorescein probes with specific selectivity, and specifically discloses a preparation method of fluorescein probes with specific selectivity. The method comprises: (1) mixing 4-nitrophthalic anhydride, resorcinol, nitrocyclohexane and anhydrous cobalt chloride, heating and melting, adding zinc chloride, reacting, and then adding hydrochloric acid Reflux, filter and wash, dry; (2) will contain Na 2 S and Na 2 SO 3 The reducing solution is mixed with the product of step (1), reacted, and then glacial acetic acid is added dropwise until the precipitation is complete, filtered, washed, and dried; (3) the mixed solvent containing methanol and triethylamine is mixed with the product of step (2) Mix, add CS dropwise 2 , to react, then add copper chloride aqueous solution dropwise, continue the reaction after dropping, then adjust the pH value of the system to 1-2 with hydrochloric acid, distill under reduced pressure, wash, dry, and purify by column chromatography. The method greatly improves the conversion rate and yield of 5-fluorescein isothiocyanate.

Description

technical field [0001] The present application relates to the field of preparation of fluorescein probes with specific selectivity, and more particularly, to a preparation method of fluorescein probes with specific selectivity. Background technique [0002] Fluorescein probes are a class of fluorescein and its derivatives that interact with target molecules to change the fluorescence spectrum (including fluorescence intensity, fluorescence excitation and emission wavelengths, fluorescence lifetime, and fluorescence polarization / anisotropy, etc.) to realize the detection of target molecules. The organic fluorescent functional dye for detection has the advantages of low detection limit and high sensitivity, and is especially suitable for the relevant specific detection of some low-content substances, especially biological materials. [0003] Fluorescein isothiocyanate (Fluorescein isothiocyanate, 5-FITC) is one of the most widely used fluorescently labeled probes, with a maxim...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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