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The preparation method of 5,6-dihydro-6-(2-naphthyl)imidazo[2,1-b]thiazole oxalate

A technology of thiazole oxalate and imidazolo, which is applied in the field of biochemistry and analysis, can solve the problems of strong corrosion, pollution, non-compliance and other problems of equipment, and achieve the effect of short reaction route, simple operation and low cost

Active Publication Date: 2021-12-28
SUZHOU BAILINGWEI HYPERFINE MATERIAL
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] The first step of this route is to use 2-naphthylethanone as a raw material, directly carry out bromination with bromine, a large amount of hydrogen bromide gas will be produced, which is very polluting, highly corrosive to equipment, and the yield is also low; the third The first step uses acetyl chloride as a protective reagent, and a large amount of hydrogen chloride gas will be produced during the reaction process, which is highly polluting and highly corrosive to equipment; the fifth step uses thionyl chloride as a condensation agent, and a large amount of sulfur dioxide and hydrogen chloride gas will be produced during the reaction process. High pollution and strong corrosion to equipment
[0006] This operational route does not meet the requirement of green synthesis, therefore, look for a kind of industrialized production method of green synthesis 5,6-dihydro-6-(2-naphthyl) imidazo[2,1-b]thiazole oxalate is of great significance

Method used

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  • The preparation method of 5,6-dihydro-6-(2-naphthyl)imidazo[2,1-b]thiazole oxalate
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  • The preparation method of 5,6-dihydro-6-(2-naphthyl)imidazo[2,1-b]thiazole oxalate

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preparation example Construction

[0034] In order to achieve the above object, the invention provides a kind of 5,6-dihydro-6-(2-naphthyl) imidazo[2,1-b]thiazole oxalate preparation method, comprising:

[0035] Step 1: Add 2-vinylnaphthalene as a raw material, hydrogen peroxide and halogenated products to the solvent, without adding a catalyst or adding a catalyst, react in the reaction temperature range of -20°C-200°C to obtain a halogenated intermediate, the hydrogen peroxide The amount used is 0.5-5 equivalents, and the amount of the halogenated compound is 1-10 equivalents;

[0036]

[0037] Step 2: Add 2-aminothiazole and a solvent to the halogenated intermediate obtained in Step 1, without adding a catalyst or adding a catalyst, and react at a reaction temperature range of -20°C to 200°C to obtain a thiazole intermediate. The consumption of 2-aminothiazole is 0.8-2 equivalent;

[0038]

[0039] Step 3: Add an oxalic acid compound and a solvent to the thiazole intermediate obtained in Step 2, and r...

Embodiment 1

[0049] Embodiment 1, under room temperature condition and mechanical stirring, add solvent 15L water or 20L ethyl acetate or 12L DMF or 20L acetone or 25L toluene or 22L xylene successively in 50L reactor, halide 2.4kg sodium bromide or 3.1 kg potassium bromide or 2.1kg ammonium bromide or 1.4kg lithium chloride or 1.6kg sodium chloride or 2.0kg potassium chloride or 1.3kg ammonium chloride or 0.9kg lithium fluoride or 1.0kg sodium fluoride or 1.1kg fluoride Potassium chloride or 1.0kg ammonium fluoride or 2.9kg lithium iodide or 3.3kg sodium iodide or 3.8kg potassium iodide or 3.2kg ammonium iodide or 3.6kg N-bromosuccinimide or 2.9kg N-chlorosuccinyl Imine or 4.7kg N-iodosuccinimide, and catalyzer 1kg732 strongly acidic cation exchange resin, or do not add catalyzer, stir to dissolve clear, then add the raw material 2-vinylnaphthalene of 3.08Kg wherein, stir evenly, Add 2.3kg of 35% hydrogen peroxide dropwise to it, and drop it within 1 hour; stir the reaction at room temper...

Embodiment 2

[0060] Example 2, at room temperature and under mechanical stirring, 12L DMSO, 2.2kg of lithium bromide as a halide, and 2kg of 724 weakly acidic cation exchange resin as a catalyst were successively added to a 50L reactor, stirred evenly to dissolve, and then 3.08Kg was added thereto The raw material 2-vinylnaphthalene was stirred well, and 2.3kg of 35% hydrogen peroxide was added dropwise to it, and the drop was completed within 1 hour; the reaction was stirred at room temperature for 1 hour, and then the temperature was gradually changed to 100°C, and the reaction was kept for 6 hours to obtain the reaction liquid, which was monitored by HPLC at the same time Reaction, and then confirm whether the reaction is complete.

[0061] Cool the reaction solution to 25°C, add sodium sulfite to it until no bubbles emerge and the color of the reaction solution does not continue to change; continue to cool the reaction solution to 0°C-5°C, at this time the reaction solution precipitates...

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Abstract

The invention discloses a preparation method of 5,6-dihydro-6-(2-naphthyl)imidazo[2,1-b]thiazole oxalate, comprising step 1: adding 2-vinyl to the solvent Naphthalene is the raw material, hydrogen peroxide and brominated compounds, and a catalyst is added to react in the reaction temperature range of -20°C to 200°C to obtain brominated intermediates. The amount of hydrogen peroxide is 0.5-5 equivalents, and the amount of brominated compounds is 1 ‑10 equivalents; step 2: add 2‑aminothiazole and solvent to the brominated intermediate obtained in step 1, without catalyst, react in the reaction temperature range of ‑20°C-200°C to obtain the thiazole intermediate, the The amount of 2-aminothiazole is 0.8-2 equivalents; Step 3: Add one or both of dihydrate oxalic acid and anhydrous oxalic acid and a solvent to the thiazole intermediate obtained in step 2, at -20°C-300°C Reaction in the reaction temperature range obtains 5,6-dihydro-6-(2-naphthyl) imidazo[2,1-b]thiazole oxalate. The reaction route is short and the pollution is small.

Description

technical field [0001] The invention relates to the fields of biochemistry and analysis, in particular to a preparation method of 5,6-dihydro-6-(2-naphthyl)imidazo[2,1-b]thiazole oxalate. Background technique [0002] 5,6-Dihydro-6-(2-naphthyl)imidazo[2,1-b]thiazole oxalate is a highly efficient detection substrate for alkaline phosphatase, mainly used in in vitro diagnosis of alkaline phosphate Enzymes and other biochemical detection fields. This product has not yet been commercialized by a domestic company, mainly because giants in the international biochemical diagnostic reagent industry such as Thermo Fisher have monopolized the product. In addition, the traditional production process of this product reported in foreign literature has significant shortcomings such as large pollution, difficult operation and low yield, which makes domestic companies temporarily unable to realize the green production of this product in China and hinders the health of my country's biochemi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04C07C55/07C07C51/41
CPCC07D495/04C07C55/07C07C51/412
Inventor 陈丕证龙韬邹增龙
Owner SUZHOU BAILINGWEI HYPERFINE MATERIAL
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