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Synthetic process of 2,6-dibromobenzothiazole

A technology of benzothiazole and synthesis process, applied in the field of synthesis technology of benzothiazole derivatives, can solve the problems of many operation steps, low yield and high cost, and achieve the effects of few operation steps, high yield and low cost

Active Publication Date: 2017-09-29
上海泰坦科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, in the synthesis method of 2,6-dibromobenzothiazole, two bromine atoms are often replaced separately, resulting in many operation steps and low final yield, resulting in low efficiency and high cost, which is not conducive to industrial development. mass production applications

Method used

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  • Synthetic process of 2,6-dibromobenzothiazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] A kind of synthetic technique of 2,6-dibromobenzothiazole, consists of the following steps:

[0014] Dissolve 0.1mol benzothiazole in 200mL chloroform, transfer to a 500mL three-necked flask equipped with a mechanical stirring paddle, a thermometer, and a spherical condenser, stir and reflux at 50°C, and then add 0.22mol N-bromosuccinimide and 0.008mol titanium dioxide were added to a three-necked flask at one time to react for 15 hours, then the obtained reaction solution was cooled to room temperature, filtered, and the filtrate was washed three times with 50mL saturated sodium bicarbonate solution until the organic phase was basically light yellow. Sodium sulfate water was dried, and the solvent was distilled off under reduced pressure to obtain a light yellow solid, which was recrystallized with 100 mL of isopropanol to obtain 22.7 g of white crystals, with a yield of 76.9%, a purity of 99.4%, and MS: m / z=293 (M + ), 1 H NMR (DMSO, 300MHz) δ: 8.91(s,1H), 8.52(d,1H)...

Embodiment 2

[0016] A kind of synthetic technique of 2,6-dibromobenzothiazole, consists of the following steps:

[0017] Dissolve 0.1mol benzothiazole in 200mL chloroform, transfer to a 500mL three-necked flask equipped with a mechanical stirring paddle, a thermometer, and a spherical condenser, stir and reflux at 45°C, and then add 0.2mol N-bromosuccinimide and 0.02mol titanium dioxide were added to a three-necked flask at one time to react for 11 hours, then the obtained reaction solution was cooled to room temperature, filtered, and the filtrate was washed three times with 50mL saturated sodium bicarbonate solution until the organic phase was basically light yellow. Sodium sulfate water was dried, and the solvent was distilled off under reduced pressure to obtain a light yellow solid, which was recrystallized with 100 mL of isopropanol to obtain 22.4 g of white crystals, with a yield of 75.8%, a purity of 99.3%, and MS: m / z=293 (M + ), 1 H NMR (DMSO, 300MHz) δ: 8.92(s,1H), 8.53(d,1H), ...

Embodiment 3

[0019] A kind of synthetic technique of 2,6-dibromobenzothiazole, consists of the following steps:

[0020] Dissolve 0.1mol benzothiazole in 200mL chloroform, transfer to a 500mL three-necked flask equipped with a mechanical stirring paddle, a thermometer, and a spherical condenser, stir and reflux at 55°C, and then add 0.23mol N-bromosuccinimide and 0.001mol titanium dioxide were added to a three-necked flask at one time to react for 13h, then the obtained reaction solution was cooled to room temperature, filtered, and the filtrate was washed three times with 50mL saturated sodium bicarbonate solution until the organic phase was basically light yellow. Sodium sulfate water was dried, and the solvent was distilled off under reduced pressure to obtain a light yellow solid, which was recrystallized with 100 mL of isopropanol to obtain 21.9 g of white crystals, with a yield of 74.4%, a purity of 99.4%, and MS: m / z=293 (M + ), 1 H NMR (DMSO, 300MHz) δ: 8.90(s,1H), 8.53(d,1H), 8.3...

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Abstract

The invention relates to a synthesizing process of 2, 6-dibromo benzothiazole. The process comprises the following steps: benzothiazole is dissolved in chloroform, the mixture is stirred at the temperature of 45 DEG C-55 DEG C and subjected to back flow, N-bromosuccinimide and titanium dioxide are added into the mixture by one time and reacted for 9-15 h, then an obtained reaction solution is cooled to the room temperature and filtered, filtrate is cleaned with a saturated sodium bicarbonate solution, anhydrous sodium sulfate is added for drying, pressure is reduced to steam a solvent, light yellow solid is obtained, isopropanol is used for recrystallization to obtain white crystals, and accordingly, 2, 6-dibromo benzothiazole is obtained. The N-bromosuccinimide adopts a brominating agent, at the same time, under the catalytic action of the titanium dioxide, bromo substitution of benzothiazole on site 2 and site 6 can be realized through further reaction, the operation steps are few, the yield is high, a catalyst is easy to obtain, the cost is low, and the synthesizing process is suitable for industrial large-scale production of the 2, 6-dibromo benzothiazole.

Description

technical field [0001] The invention relates to a synthesis process of benzothiazole derivatives, in particular to a synthesis process of 2,6-dibromobenzothiazole. Background technique [0002] Benzothiazoles are a class of extremely important heterocyclic compounds, which are widely used in medicine, pesticides, materials engineering and other fields. For example, in medicine, benzothiazole compounds can be used as fungicides, fungicides, etc., and can also be used for anti-parasite, anti-tuberculosis, anti-rheumatism and anti-cancer; in agriculture, benzothiazole compounds have anti-agricultural Fungi, insecticide, weed control, plant growth regulation and other activities; in the field of materials engineering, benzothiazole compounds can be used as rubber vulcanization accelerators, plastic dyes, ultraviolet absorbers in cosmetics and sunglasses, liquid crystal display materials, electro- Luminescent materials and fluorescent probe materials, etc. In particular, 2,6-di...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/68
CPCC07D277/68
Inventor 谢应波张庆张华徐肖冰罗桂云
Owner 上海泰坦科技股份有限公司