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Electrochemical synthesis method of thiazole compounds

An electrochemical and thiazole technology, which is applied in the field of thiazole compound preparation, can solve the problems that the synthesis of thiazole compounds has not been reported in domestic and foreign literature, the post-processing process is complicated, and the environmental pollution is serious, and the cost is low, the equipment cost is low, and the experimental operation is simple. Effect

Active Publication Date: 2020-08-21
BEIJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] (1) It is necessary to use stoichiometric quinone oxidants, which is a serious waste and a great environmental hazard;
[0015] (2) Use highly toxic benzene as a solvent, which is very dangerous;
[0016] (3) The reaction temperature is high, the operation is inconvenient, the post-treatment process is complicated, a large amount of waste water will be generated, and the environmental pollution is serious
[0017] At present, the one-pot synthesis of thiazole compounds through electrochemical catalysis has not been reported in the literature at home and abroad.

Method used

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  • Electrochemical synthesis method of thiazole compounds
  • Electrochemical synthesis method of thiazole compounds
  • Electrochemical synthesis method of thiazole compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0040] Example 1: Synthesis of 4,5-dimethyl-2-isobutylthiazole by electrochemical method

[0041] In a 50ml single-chamber electrolytic cell, add 4,5-dimethyl-2-isobutylthiazoline (1.0mmol), sodium bromide (1.0mmol), and tetrachlorohydroquinone (0.5mmol) to 5ml In the mixed two-phase solvent system of methyl chloride and 5ml water, graphite sheet electrode is used as anode, stainless steel mesh is used as cathode, and the temperature is 3mA / cm 2 Electrolysis under constant current, stirring at 40°C, stop electrolysis when the energization reaches 3.0F / mol, after cooling to room temperature, extract with dichloromethane, and wash with sodium hydroxide aqueous solution (0.5M) and water three times each, and pass through the column Chromatographic separation yielded 4,5-dimethyl-2-isobutylthiazole. Yield: 41%.

[0042]

[0043] Yellow liquid; 1 H NMR(400MHz, CDCl 3 )δ0.97(d,J=6.8Hz,6H),1.96-2.08(m,1H), 2.29(s, 3H), 2.30(s,3H), 2.75(d,J=7.2Hz,2H); 13 C NMR(100MHz, CDCl 3 )δ 11.2, 14.6...

Embodiment 2

[0044] Example 2: Synthesis of 4,5-dimethyl-2-isobutylthiazole by electrochemical method

[0045] In a 50ml single-chamber electrolytic cell, add 4,5-dimethyl-2-isobutylthiazoline (1.0mmol), sodium bromide (1.0mmol), and tetrachlorohydroquinone (0.5mmol) to 5ml 1 , 2-Dichloroethane and 5ml water mixed two-phase solvent system, graphite sheet electrode as anode, stainless steel mesh as cathode, at 3mA / cm 2 Electrolysis under constant current, stirring at 80°C, when the energization reaches 3.0F / mol, stop electrolysis, after cooling to room temperature, extract with dichloromethane, and wash with sodium hydroxide aqueous solution (0.5M) and water three times, and pass through column Chromatographic separation yielded 4,5-dimethyl-2-isobutylthiazole. Yield: 65%.

Embodiment 3

[0046] Example 3: Synthesis of 4,5-dimethyl-2-isobutylthiazole by electrochemical method

[0047] In a 50ml single-chamber electrolytic cell, add 4,5-dimethyl-2-isobutylthiazoline (1.0mmol), sodium bromide (1.0mmol), and tetrachlorohydroquinone (0.5mmol) to 5ml 1 ,2-Dichloroethane and 5ml water mixed two-phase solvent system, graphite electrode as anode, stainless steel mesh as cathode, at 3mA / cm 2 Electrolysis under constant current, stirring at 60℃, when the energization reaches 3.0F / mol, stop the electrolysis, after cooling to room temperature, extract with dichloromethane, and wash with sodium hydroxide aqueous solution (0.5M) and water three times, and pass through the column Chromatographic separation yielded 4,5-dimethyl-2-isobutylthiazole. Yield: 38%.

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Abstract

The electrochemical synthesis method of thiazole compounds belongs to the technical field of thiazole compound preparation. The method is to use 2,5-dihydrothiazole as a raw material in a single-chamber electrolytic cell, use bromide and tetrachlorohydroquinone as catalysts in the electrolyte, and electrolyze without any additional supporting electrolyte and additives. Temperature 40~80℃, current density 1~5mA / cm 2 , after passing through 3.0-4.0F / mol electricity, the 1,3-thiazole compound is obtained. The method of the present invention first adopts the indirect electrolysis method of electrochemical catalysis with simple operation to synthesize 1,3-thiazole compound, and uses a single-chamber electrolytic cell, adopts constant current electrolysis and uses a graphite sheet electrode as a working electrode, avoiding the stoichiometric oxidant The use helps to achieve atom economy, greatly reduces the cost, simplifies the operation, and is more conducive to the realization of industrial production.

Description

Technical field [0001] The invention relates to a double-catalyzed electrochemical synthesis method of bromide and tetrachlorohydroquinone, which is used to synthesize a thiazole compound and belongs to the technical field of thiazole compound preparation. Background technique [0002] Thiazole is an important type of five-membered aromatic heterocyclic ring. It contains nitrogen and sulfur heteroatoms. Its special structure makes it widely used in medicine, pesticides, materials, biological dyes and artificial ion receptors (Xu Baocai. Perfume) Fragrance and Cosmetics, 1995(02):34-38.). For example, the antibiotic drug cefixime, the anticancer drug dasatinib, the antiparasitic drug nitazoxanide, the anti-inflammatory drug meloxicam, and a variety of insecticide and herbicide drugs all contain thiazole rings. [0003] Thiazole compounds are widely found in foods that people see every day. Because of their unique nut-like, vegetable-like, sulfur-like, baked food, meaty and burnt ar...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C25B3/02C25B3/23
CPCC25B3/23
Inventor 曾程初李勇
Owner BEIJING UNIV OF TECH
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