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Synthetic method of pyronine derivative dye

A synthesis method and derivative technology are applied in the field of synthesis of Pylonine derivative dyestuffs, which can solve the problems of low yield and long reaction time, and achieve the effects of reducing production cost, high product yield and reducing pollution.

Active Publication Date: 2015-03-25
山东埃米森生物科技有限公司
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Problems solved by technology

[0004] The present invention overcomes the shortcoming of using highly toxic potassium cyanide, long reaction time and low yield in the existing synthetic technology, and provides a simple, non-toxic and efficient synthetic method of pyronin derivative dyes

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  • Synthetic method of pyronine derivative dye
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  • Synthetic method of pyronine derivative dye

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Embodiment Construction

[0017] 1. Synthesis of pyronine thione or ketone, taking thione as an example

[0018] Steps: Add 0.5 (1.66 mmol) pyronin Y and 0.53 g (16.6 mmol) sulfur to a 50 ml round bottom flask at room temperature, then add 20 ml of refined tetrahydrofuran, then add 0.056 g (4.98 mmol) while stirring Potassium tert-butoxide, after the addition, put the reaction bottle into an oil bath, and heat under reflux at 70°C for 10 hours. Then the above reaction system was cooled to room temperature, filtered, the filter cake was washed with dichloromethane, and the filtrate was spin-dried and purified by column chromatography (eluent: PE:DCM=1:1) to obtain pyroninthione 0.27 g, the yield is 55%. 1 H NMR (300 MHz, CDCl 3 ) δ 8.70 (d, J = 9.2 Hz, 2H), 6.75 (dd, J = 9.2, 2.3 Hz, 2H), 6.43 (d, J = 2.3Hz, 2H), 3.13 (s, 12H). 13 C NMR (75 MHz, CDCl 3 ) δ 196.26, 154.58 , 153.03 , 131.80 , 120.07 , 110.52 , 96.06 , 40.24 . ESI-MS: [M+H] + =299.2.

[0019] 2. Synthesis of Thiopyronine Der...

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Abstract

The invention discloses a synthetic method of a pyronine derivative dye. The synthetic method comprises the following steps: with pyronine as a raw material, producing carbine serving as an intermediate under the action of potassium tert-butoxide, carrying out reaction on carbine and sulfur or oxygen to produce pyronine thione or ketone, and then carrying out reaction on pyronine thione and amine or halohydrocarbon to produce the pyronine derivative dye. The synthetic method is safe and simple in operation, short in reaction time and good in yield and purity of the pyronine derivative dye.

Description

technical field [0001] The invention relates to a method for synthesizing pyronine derivative dyes. Background technique [0002] Pyronine derivatives are a class of excellent dyes, which have the advantages of good stability and high fluorescence quantum yield. When the substituting element on the 9-position is sulfur, the dye gives strong red fluorescence; when it is nitrogen, it gives strong green fluorescence. However, the synthesis of this type of dye is relatively difficult at present. The general synthesis method is to first oxidize pyronine into a ketone, and then the ketone carries out a nucleophilic substitution reaction with a nucleophile under the catalysis of trifluoromethanesulfonic anhydride to generate the target product. The process needs to go through 5 steps in total, which takes a long time and has low yield, and a large amount of highly toxic substance potassium cyanide is used in the oxidation step. Therefore, it is very necessary to develop new synth...

Claims

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Application Information

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IPC IPC(8): C09B57/00
Inventor 吴学周鑫曾义英柳志学石连生李彩梅
Owner 山东埃米森生物科技有限公司
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