Synthesis process of sulfonic-group rhodamine compound

A synthesis process and compound technology are applied in the field of synthesis technology of sulforhodamine compounds, which can solve the problems of high price of sulfonyl fluorescein, increase production cost, low synthesis yield and the like, and achieve energy saving in production cost and production safety. Improve the effect of simplifying the operation steps

Inactive Publication Date: 2019-04-12
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional process for preparing sulforhodamine dyes is synthesized from sulfonyl fluorescein, but sulfonyl fluorescein is expensive, unstable, easy to hydrolyze, and the synthesis yield is low, often producing a large amount of waste acid. Moreover, the operation is cumbersome and has certain dangers, which greatly increases the production cost

Method used

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  • Synthesis process of sulfonic-group rhodamine compound
  • Synthesis process of sulfonic-group rhodamine compound
  • Synthesis process of sulfonic-group rhodamine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] N 2 Under protection, add 9.0g of saccharin solid and 13mL of concentrated sulfuric acid (concentration: 98%) in sequence in a 50mL three-necked flask, stir and react at 140°C for 2h, then cool to room temperature, a large amount of solids are precipitated in the reaction mixture, filter, and filter the resulting solid Wash with ice water and dry to obtain 7.3 g of o-sulfobenzoic anhydride white solid with a structure represented by formula (I), with a yield of 81%.

[0029] The obtained compound with the structure shown in formula (I) is carried out nuclear magnetic spectrum analysis, and the results are as follows: 1 HNMR (500MHz, CDCl3) δ8.77(d, J=7.3Hz, 1H), 8.05(d, J=7.3Hz, 1H), 7.76(t, J=2.2Hz, 1H), 7.53(t, J= 8.5Hz, 1H).

[0030] 4.8g of diethylamine and 0.3mL of phosphoric acid (weight concentration is 85%) are fully mixed in 20mL of toluene, prepared to form a reaction raw material solution; N 2 Under protection, slowly drop the above prepared reaction raw m...

Embodiment 2

[0034] in N 2 Under protection, add 9.0g of saccharin solid and 10.5mL of concentrated sulfuric acid (concentration: 98%) in sequence in a 50mL three-neck flask, stir and react at 140°C for 2h, then cool to room temperature, a large amount of solids are precipitated in the reaction mixture, filter, and filter the obtained The solid was washed with ice water and dried to obtain 6.3 g of o-sulfobenzoic anhydride as a white solid with a yield of 70%.

[0035] 5.4g of diethylamine and 0.4mL of phosphoric acid (weight concentration is 85%) are fully mixed in 25mL of toluene, prepared to form a reaction raw material solution; N 2 Under protection, slowly drop the above prepared reaction raw material solution into a mixture of 9.1g resorcinol and 20mL toluene at a rate of 1 drop per second, heat and reflux at 55°C for 10h, cool to room temperature, and let it stand Separate the layers and separate the organic layer, wash the organic layer with water, and finally spin dry the solvent...

Embodiment 3

[0039] in N 2 Under protection, add 100.0g of saccharin solid and 155mL of concentrated sulfuric acid (concentration: 98%) to a 500mL three-neck flask successively, stir and react at 145°C for 3h, then cool to room temperature, a large amount of solids are precipitated in the reaction mixture, filter, and filter the resulting solid Wash with ice water and dry to obtain 87.5 g of o-sulfobenzoic anhydride as a white solid with a yield of 87%.

[0040] 193.4g of diethylamine and 10.0mL of phosphoric acid (weight concentration is 85%) are fully mixed in 400mL of toluene, prepared to form a reaction raw material solution; N 2 Under protection, slowly drop the above prepared reaction raw material solution into a mixture of 300.0g resorcinol and 600mL toluene at a rate of 1 drop per second, heat the reaction at 50°C for 12h, cool to room temperature, and let stand to separate and the organic layer was separated, the organic layer was washed with water, and finally the solvent was sp...

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Abstract

The invention discloses a synthesis process of a sulfonic-group rhodamine compound. The process comprises the steps: mixing saccharin and a protonic acid catalyst, performing heating for a reaction soas to obtain a compound shown in a formula (I), performing a reaction between a compound shown in a formula (II) and resorcinol through heating under the action of the protonic acid catalyst so as toobtain a compound shown in a formula (III), performing a reaction between the compound of the formula (I) and the compound in the formula (III) through heating under the action of a Lewis acid catalyst under the conditions of nitrogen protection and light shielding so as to obtain the sulfonic-group rhodamine compound shown in a formula (IV). Through the synthesis process, the use of thionyl chloride in a conventional process is avoided, the operation is simplified, the production safety is improved, the pollution to the environment is little, the reaction can be carried out under normal pressure, and the reaction has a high selectivity; and the chemical structural formulas of the compounds represented separately by the formula (I), the formula (II), the formula (III) and the formula (IV)are shown.

Description

technical field [0001] The invention relates to a synthesis process of a sulforhodamine compound. Background technique [0002] Sulforhodamine dye is an excellent organic dye with easy structure modification and excellent optical properties. It can be used to prepare functional dyes and has broad application prospects in the dye field. Using xanthene-type rhodamine as the matrix, the introduction of amino-substituted groups and water-soluble sulfonic acid groups can reduce the electron cloud density on the dye matrix molecules, increase the flexibility of the dye matrix molecules, and then improve their light resistance and light resistance. Ozone, water resistance, increase the solubility and stability of dye molecules. The traditional process for preparing sulforhodamine dyes is synthesized from sulfonyl fluorescein, but sulfonyl fluorescein is expensive, unstable, easy to hydrolyze, and the synthesis yield is low, often producing a large amount of waste acid. And the op...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/82
CPCC07D311/82
Inventor 李郁锦周子淳高建荣叶青
Owner ZHEJIANG UNIV OF TECH
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