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Electrochemical synthesis method of thiazoles compound

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 environment is seriously polluted. It achieves low cost, low equipment cost, and simple experimental operation. Effect

Active Publication Date: 2019-02-12
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 thiazoles compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0041] In a 50ml single-chamber electrolytic cell, 4,5-dimethyl-2-isobutylthiazoline (1.0mmol), sodium bromide (1.0mmol), tetrachlorohydroquinone (0.5mmol) were added to 5ml di In the mixed two-phase solvent system of methyl chloride and 5ml water, with the graphite sheet electrode as the anode and the stainless steel mesh as the cathode, at 3mA / cm 2 Electrolyze under constant current, stir at 40°C, stop electrolysis when the current flow reaches 3.0F / mol, cool to room temperature, extract with dichloromethane, wash with sodium hydroxide aqueous solution (0.5M) and water three times, pass through the column Chromatographic separation gives 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 )δ11.2, 14.6, 22.3, 29....

Embodiment 2

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

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

Embodiment 3

[0046] Example 3: Electrochemical synthesis of 4,5-dimethyl-2-isobutylthiazole

[0047] In a 50ml single-chamber electrolytic cell, 4,5-dimethyl-2-isobutylthiazoline (1.0mmol), sodium bromide (1.0mmol), tetrachlorohydroquinone (0.5mmol) were added to 5ml 1 , In the mixed two-phase solvent system of 2-dichloroethane and 5ml water, with the graphite sheet electrode as the anode and the stainless steel mesh as the cathode, at 3mA / cm 2 Electrolyze under constant current, stir at 60°C, stop electrolysis when the current flow reaches 3.0F / mol, cool to room temperature, extract with dichloromethane, wash with sodium hydroxide aqueous solution (0.5M) and water three times, pass through the column Chromatographic separation gives 4,5-dimethyl-2-isobutylthiazole. Yield: 38%.

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Abstract

The invention provides an electrochemical synthesis method of a thiazoles compound and belongs to the technical field of thiazoles compound preparation. According to the method, in a single-chamber electrolytic tank, 2,5-thiazoline is used as a raw material, in an electrolytic solution, bromide and tetrachlorohydroquinone serve as catalysts, electrolysis is carried out on the condition without adding supporting electrolyte and additive, the reaction temperature ranges from 40 DEG C to 80 DEG C, current density ranges from 1 mA / cm2 to 5 mA / cm2, and after 3.0-4.0 F / mol of electric quantity is introduced, the 1,3-thiazole compound is obtained. According to the method, the electrochemical catalysis indirect electrolysis method easy to operate is adopted firstly to synthesize the 1,3-thiazole compound, the single-chamber electrolytic tank is used, constant-current electrolysis is adopted, a graphite flake electrode is used as a working electrode, use of chemometry oxidizing agents is avoided, atom economy is achieved beneficially, the cost is reduced greatly, operation is easy, and industrialized production is achieved beneficially.

Description

technical field [0001] The invention relates to a double-catalyzed electrochemical synthesis method of bromide and tetrachlorhydroquinone, which is used for synthesizing thiazole compounds and belongs to the technical field of thiazole compound preparation. Background technique [0002] As a class of important five-membered aromatic heterocycles, thiazoles contain nitrogen and sulfur heteroatoms, and their special structures make them 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 many insecticides and herbicides all contain thiazole rings. [0003] Thiazoles are widely found in foods that people see every day. Due to their unique nut-like, vegetable-like, sulfur-like, baked food, meat and burnt aromas, they can be w...

Claims

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Application Information

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