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Preparation method of 2-chloro-6-methoxybenzothiazole

A technology of methoxybenzene and thiazole, which is applied in the field of preparation of 2-chloro-6-methoxybenzothiazole, can solve problems such as restricting industrialized large-scale production, restricting industrialized production, and increasing production costs, and achieves reagents and Effects of low drug toxicity, low cost, and increased yield

Inactive Publication Date: 2019-03-12
安徽工大化工科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] During the preparation of 2-chloro-6-methoxybenzothiazole, the coupling reaction is very easy to occur, which greatly affects the yield
It is also reported that in order to improve the yield, isoamyl nitrite can be used as a diazotization reagent, but this method increases the production cost a lot, thus restricting industrial production to a certain extent
According to literature reports, its existing synthesis method has the following disadvantages, such as harsh conditions, high cost, difficult operation, low conversion rate, long reaction route, long reaction time, low yield, etc., which greatly restricts its industrialization. mass production

Method used

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  • Preparation method of 2-chloro-6-methoxybenzothiazole

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Take 25g of 2-amino-6-methoxybenzothiazole in a 500ml three-necked flask, add 100ml of ethanol and stir to dissolve, add 15ml of hydrochloric acid solution with a volume fraction of 15%, control the temperature in the three-necked flask to 15°C, add volume Fraction is 40g of 25% sodium nitrite solution, after 3 hours, it is detected by TLC method that the reaction of raw materials is complete. Prepare 30ml of hydrochloric acid solution with a volume fraction of 15%, add 0.5g cuprous chloride to the prepared hydrochloric acid solution, heat to 60°C, slowly add the hydrochloric acid solution containing cuprous chloride to the solution that has completed the above reaction, After 2 hours of reaction, bubbles were formed during the reaction. After the reaction was completed and cooled to room temperature, the reaction liquid had a layering phenomenon, and the oily substance in the lower layer was separated, and recrystallized with ethyl acetate petroleum ether to obtain 19....

Embodiment 2

[0030] Take 50g of 2-amino-6-methoxybenzothiazole and place it in a 500ml three-neck flask, add 200ml of ethanol and stir to dissolve, and add 80g of sodium nitrite solution with a volume fraction of 25%. Control the temperature in the three-necked flask to 15°C, add 30ml of hydrochloric acid solution with a volume fraction of 15% dropwise for 3 hours, and then detect the completion of the reaction of the raw materials by TLC method. Slowly add 10% sodium thiosulfate solution dropwise, and the starch potassium iodide test paper does not show blue. Prepare 60ml of hydrochloric acid solution with a volume fraction of 15%, add cuprous chloride 1.0g to the prepared hydrochloric acid solution, heat to 60°C, slowly add the hydrochloric acid solution containing cuprous chloride to the solution that has completed the above reaction, After 2 hours of reaction, bubbles were formed during the reaction. After cooling to room temperature, the reaction liquid had layering phenomenon, and t...

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Abstract

The invention discloses a preparation method of 2-chloro-6-methoxybenzothiazole, and belongs to the field of medical intermediates. The method comprises the following steps: dissolving 2-amino-6-methoxybenzothiazole in an organic solvent, adding a hydrochloric acid solution, dropwise adding a sodium nitrite solution, and after completion of the reaction, adding a hydrochloric acid solution containing a catalyst, cooling, and recrystallizing to obtain a target product. The preparation method disclosed by the invention is simple, the raw materials are easy to obtain, the reagents and drugs usedin an operation process are relatively low in toxicity, reaction conditions are mild, the time is short, the yield is high, the cost is low, three wastes are little, and the target product is high incontent and high in purity, and the suitability for industrial production is achieved.

Description

technical field [0001] The invention belongs to the field of synthesis of pharmaceutical intermediates, in particular to a preparation method of 2-chloro-6-methoxybenzothiazole. Background technique [0002] 2-chloro-6-methoxybenzothiazole is as a kind of important pharmaceutical intermediate, and its structural formula is as shown in I: [0003] [0004] During the preparation of 2-chloro-6-methoxybenzothiazole, the coupling reaction is very easy to occur, thereby greatly affecting the yield. It is also reported that in order to increase the yield, isoamyl nitrite can be used as a diazotization reagent, but this method increases the production cost a lot, thus restricting industrial production to a certain extent. According to literature reports, its existing synthesis method has the following deficiencies, such as harsh conditions, high cost, difficult operation, low conversion rate, long reaction route, long reaction time, low yield, etc., which greatly restricts its ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/68
CPCC07D277/68
Inventor 宋丰发许立信万超黄国正
Owner 安徽工大化工科技有限公司
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