Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

Synthetic method of pentadeuterium-substituted malachite green salt

A synthesis method, malachite green technology, applied in the direction of organic chemistry methods, chemical instruments and methods, carboxylate preparation, etc., can solve problems such as unsuitable synthesis of malachite green salt, harsh conditions, unsuitable synthesis methods, etc.

Active Publication Date: 2019-11-22
SHANGHAI INST OF MEASUREMENT & TESTING TECH
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009]On the one hand, the above-mentioned traditional synthesis method has harsh conditions and complicated steps, and what is more serious is that too many impurities are produced, which are not easy to separate, so they are not suitable as candidates for reference materials synthetic method
[0010]On the other hand, it is even more difficult to synthesize deuterium-substituted malachite green by using the above-mentioned traditional method of synthesis of malachite green, it is easy to produce hydrogen deuterium in the reaction exchange, not suitable for the synthesis of highly abundant deuterium-substituted malachite green salts

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthetic method of pentadeuterium-substituted malachite green salt
  • Synthetic method of pentadeuterium-substituted malachite green salt
  • Synthetic method of pentadeuterium-substituted malachite green salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Preparation of pentadeuterium-substituted leuco malachite green

[0056] Step a): preparation of pentadeuterium substituted tert-butyl benzoate;

[0057] Add octadeuterium-substituted toluene (3.5mL, 33mmol), potassium permanganate (12.01g, 76mmol), sodium carbonate (1.48g, 14mmol) and 100mL of water into a 250mL flask, reflux for 8h and cool to room temperature . After filtering with diatomaceous earth, it is acidified with hydrochloric acid with a concentration of 4mol / L, and then extracted three times with dichloromethane. After washing with water, the combined organic phase is dried with anhydrous sodium sulfate. After filtering, the solvent is removed under reduced pressure to obtain the compound shown in formula (2). Deuterium-substituted benzoic acid;

[0058] Take 50 mL of the obtained pentadeuterium-substituted benzoic acid, add 1 mL of concentrated sulfuric acid, tert-butanol (3.2 mL, 35 mmol), and 1 g of magnesium sulfate, reflux for 2 h and cool to room te...

Embodiment 2

[0074] Preparation of pentadeuterium-substituted malachite green tartrate

[0075] The pentadeuterium-substituted leuco malachite green crude product obtained in Example 1 (5.03 g, 15 mmol), 100 mL of methanol, and 10 mL of tartaric acid aqueous solution with a concentration of 1 mol / L were added to a 250 mL flask, and refluxed for 1 h. After cooling, let the liquid separation separate the organic phase and the water phase; get the water phase after the liquid separation and extract it three times with ether; combine the organic phase obtained by the liquid separation and the organic phase obtained by the extraction, and wash the combined organic phase with water, Then dry it with anhydrous sodium sulfate, filter and remove the solvent under reduced pressure; the obtained crude product is chromatographed by methanol / chloroform column to obtain 6.88 g of pentadeuterium-substituted malachite green tartrate, with a yield of 51%.

[0076] The H NMR spectrum data of malachite green...

Embodiment 3

[0081] Preparation of pentadeuterium-substituted malachite green chloride

[0082] Malachite green chloride, the chloride salt of malachite green.

[0083] The pentadeuterium-substituted leuco malachite green crude product obtained in Example 1 (5.03 g, 15 mmol), 100 mL of methanol, and 1 mL of concentrated hydrochloric acid (concentration: 12 mol / L) were added to a 250 mL flask, and refluxed for 1 h. After cooling, let the liquid separation separate the organic phase and the water phase; get the water phase after the liquid separation and extract it three times with ether; combine the organic phase obtained by the liquid separation and the organic phase obtained by the extraction, and wash the combined organic phase with water, Then dry it with anhydrous sodium sulfate, filter and remove the solvent under reduced pressure; the obtained crude product is chromatographed on a methanol / chloroform column to obtain 2.47 g of pentadeuterium-substituted malachite green chloride, with...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a synthetic method of pentadeuterium-substituted malachite green salt. According to the method disclosed by the invention, a traditional synthesis method in the prior art is completely abandoned; instead, a new synthetic route is employed, wherein the method comprises the following steps: firstly, preparing a Grignard reagent and pentadeuterium substituted tert-butyl benzoate; then the pentadeuterium-substituted leucomalachite green is synthesized in a nucleophilic addition mode; it is unexpectedly found that few by-products are synthesized through the method, the yield of the products is high, and pentadeuterium-substituted malachite green salt prepared from the synthesized pentadeuterium-substituted leucomalachite green is few in impurity and can serve as a high-quality candidate of malachite green standard substances. More importantly, in a traditional synthesis method, hydrogen-deuterium exchange is extremely easy to occur in the reaction process, and high-abundance deuterium-substituted malachite green salt is difficult to synthesize; however, unnecessary hydrogen-deuterium exchange can be avoided in the method, so that the high-abundance deuterium-substituted malachite green salt can be obtained under mild reaction conditions.

Description

technical field [0001] The invention relates to a synthesis method of pentadeuterium-substituted malachite green salt, which belongs to the technical field of chemical synthesis. Background technique [0002] Malachite green is a synthetic triphenylmethane organic compound. It is not only a dye, but also a fungicide, bactericide, and parasite-killer drug. It has special effects on saprolegniasis in fish and fish eggs (currently It is the only effective drug against saprolegniasis on the market), and it can also be used to treat gill mold disease, small melon worm disease, trichotillomaniasis, ringworm disease, oblique tube worm disease, third generation worm disease and some other bacterial diseases. [0003] However, malachite green is potentially carcinogenic, and long-term excessive use can cause cancer. Therefore, it has been listed as a banned drug for edible aquatic products by the Ministry of Agriculture of my country, and its addition is explicitly prohibited by the ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/00C07C215/68C07C51/41C07C59/255
CPCC07C213/00C07C51/412C07C67/08C07C51/16C07F3/02C07B59/001C07B2200/05C07C215/68C07C59/255C07C69/78C07C63/06
Inventor 李杰李永利陈鹰
Owner SHANGHAI INST OF MEASUREMENT & TESTING TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com