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Method for synthesizing 2-substituted benzothiazole derivative

A technology of benzothiazole and derivatives, applied in the field of catalyzing drug synthesis, can solve problems such as expensive and difficult to obtain

Inactive Publication Date: 2013-03-20
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Reaction raw materials are mostly expensive and not readily available
This also makes them subject to certain restrictions in industrial production

Method used

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  • Method for synthesizing 2-substituted benzothiazole derivative
  • Method for synthesizing 2-substituted benzothiazole derivative
  • Method for synthesizing 2-substituted benzothiazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1: the synthesis of 2-phenylbenzothiazole

[0050] 249mg (1mmol) 2-nitroiodobenzene, 53mg benzaldehyde (0.5mmol), 601mg sodium sulfide nonahydrate (2.5mmol), cuprous iodide 10mg (0.05mmol), ligand 1,10-Phen20mg (0.1mmol ) and solvent 2ml AcOH were added to a 25ml sealed tube under air environment. Then put the sealed tube into an oil bath at 100°C for 12 h. After the reaction, the reaction solution was cooled to room temperature, diluted with ethyl acetate, and washed with saturated sodium bicarbonate and water. The organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was distilled under reduced pressure and separated by silica gel column chromatography (ethyl acetate / petroleum ether: 1 / 12 as eluent) to obtain 49.6 mg of a colorless solid with a yield of 87%. .

[0051] 1 H NMR (400MHz, CDCl 3 ):δ8.07-8.10(m,3H),7.90(t,J=8.0Hz,1H),7.48-7.50(m,4H),7.38(t,J=8.0Hz,1H).

[0052] 13 C NMR (100MHz, CDCl 3 ): δ168.04, 154.06, 134...

Embodiment 2

[0054] Embodiment 2: the synthesis of 2-(4-methylphenyl) benzothiazole

[0055] 249mg (1mmol) 2-nitroiodobenzene, 60mg 4-methylbenzaldehyde (0.5mmol), 601mg sodium sulfide nonahydrate (2.5mmol), cuprous iodide 10mg (0.05mmol), ligand 1,10-Phen 20mg (0.1 mmol) and solvent 2ml AcOH were added to a 25ml sealed tube under air environment. Then put the sealed tube into an oil bath at 100°C for 12 h. After the reaction, the reaction solution was cooled to room temperature, diluted with ethyl acetate, and washed with saturated sodium bicarbonate and water. The organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was distilled under reduced pressure and separated by silica gel column chromatography (ethyl acetate / petroleum ether: 1 / 12 as eluent) to obtain 50.4 mg of a colorless solid with a yield of 84%. .

[0056] 1 H NMR (400MHz, CDCl 3 ):δ8.05(d,J=8.0Hz,1H),7.97(d,J=8.0Hz,2H),7.87(d,J=8.0Hz,1H),7.47(t,J=8.0Hz,1H ),7.35(t,J=8.0Hz,1H),7.28(d,J=8.0Hz...

Embodiment 3

[0059] Embodiment 3: the synthesis of 2-(2-methylphenyl) benzothiazole

[0060] 249mg (1mmol) 2-nitroiodobenzene, 60mg 2-methylbenzaldehyde (0.5mmol), 601mg sodium sulfide nonahydrate (2.5mmol), cuprous iodide 10mg (0.05mmol), ligand 1,10-Phen 20mg (0.1 mmol) and solvent 2ml AcOH were added to a 25ml sealed tube under air environment. Then put the sealed tube into an oil bath at 100°C for 12 h. After the reaction, the reaction solution was cooled to room temperature, diluted with ethyl acetate, and washed with saturated sodium bicarbonate and water. The organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was distilled under reduced pressure and separated by silica gel column chromatography (ethyl acetate / petroleum ether: 1 / 12 as eluent) to obtain 49.2 mg of a colorless solid with a yield of 82%. .

[0061] 1 H NMR (400MHz, CDCl 3 ):δ8.10(d,J=8.4Hz,1H),7.90(d,J=8.8Hz,1H),7.75(d,J=7.2Hz,1H),7.50(t,J=7.6Hz,1H ),7.38(t,J=8.0Hz,1H),7.29-7.35(m,3H...

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Abstract

The invention discloses a method for synthesizing a 2-substituted benzothiazole derivative. A copper compound is used to catalyze substituted o-nitro-iodobenzene and aryl formaldehyde or aromatic heterocyclic formaldehyde by a copper compound in air or sealed environment, and the reaction is carried out in one reactor under the existence of sodium sulfide to generate the 2-substituted benzothiazole derivative. The copper catalyst adopted by the method has low cost and is easy to obtain and recover. In addition, the method can realize the synthesis of a series of 2-substituted benzothiazole and derivatives at high yield in the mild condition and is beneficial to industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing 2-substituted benzothiazole derivatives and the field of metal-catalyzed drug synthesis. Background technique [0002] After Hofmann introduced 2-chloro and 2-phenylbenzothiazole for the first time in 1879, more and more benzothiazole derivatives were synthesized and widely used in pesticides, medicine and other fields. For example: in industry, it can be used as a rubber vulcanization accelerator, a dyeing agent for fibers, plastics, etc.; in agriculture, it can be used as a herbicide and insecticide; in medicine, it can be used as a fungicide, fungicide, and fungicide It can also be used as anti-parasitic, anti-tuberculosis, anti-rheumatism and anti-cancer; in addition, it can also be used as an ultraviolet absorber in cosmetics and sunglasses, and in liquid crystal displays. Liquid crystal compounds and electroluminescent and photochromic materials. [0003] The modification of benzothiazole deriv...

Claims

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Application Information

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IPC IPC(8): C07D277/66C07D417/04
Inventor 谭泽姚姗姗邓伟刘吉旦杨志勇
Owner HUNAN UNIV
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