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Preparation method of 2,6'-dichlorobenzothiazole

A technology of dichlorobenzothiazole and chlorobenzothiazole, which is applied in the field of preparation of 2,6'-dichlorobenzothiazole, can solve problems that have not been seen, and achieve the effect of simple and green synthesis process

Pending Publication Date: 2019-08-20
DALIAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

On the basis of extensive literature research, there is no one-pot preparation of 2,6'-dichlorobenzothiazole by using 2-amino-6-chlorobenzothiazole, copper chloride and isoamyl nitrite as starting materials A suitable method for this compound requires the development of a synthetic route for the preparation of the compound

Method used

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  • Preparation method of 2,6'-dichlorobenzothiazole
  • Preparation method of 2,6'-dichlorobenzothiazole
  • Preparation method of 2,6'-dichlorobenzothiazole

Examples

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Embodiment 1

[0015] This embodiment is the preparation method of 2,6'-dichlorobenzothiazole, according to the following reaction formula:

[0016]

[0017] The specific experimental process is as follows:

[0018] In a 100ml three-necked flask, 3.69g (0.02mol, 97%, 1eq) of 2-amino-6-chlorobenzothiazole was dissolved in 20ml of acetonitrile, and 2.68g (0.02mol, 1eq) of anhydrous copper chloride was added simultaneously, At room temperature, 3.51 g of isoamyl nitrite (0.03 mol, 98%, 1.5 eq) was added dropwise with magnetic stirring. After the addition, the temperature was raised to reflux, and the reaction was carried out for 2 to 3 hours. The system was a dark green solution with insoluble matter.

[0019] After the reaction was completed, acetonitrile was removed under reduced pressure, and 1.84 g of orange solid 2,6'-dichlorobenzothiazole product was obtained by column chromatography, GC: 97%, and the separation yield was 45%.

Embodiment 2

[0021] This embodiment is the preparation method of 2,6'-dichlorobenzothiazole, according to the following reaction formula:

[0022]

[0023] The specific experimental process is as follows:

[0024] In a 100ml three-necked flask, 3.69g (0.02mol, 97%, 1eq) of 2-amino-6-chlorobenzothiazole was dissolved in 20ml of acetonitrile, and 2.68g (0.03mol, 1eq) of anhydrous copper chloride was added simultaneously, At room temperature, 54 g of isoamyl nitrite (0.03 mol, 98%, 1.5 eq) was added dropwise under magnetic stirring. After the addition, the temperature was raised to reflux, and the reaction was carried out for 2 to 3 hours. The system was a dark green solution with insoluble matter.

[0025] After the reaction was completed, the acetonitrile was removed under reduced pressure, and 20 mL of ethyl acetate was added to the residue obtained from the still, washed with saturated sodium chloride, separated into layers, the organic layer was dried with anhydrous magnesium sulfate,...

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Abstract

The invention discloses a preparation method of 2,6'-dichlorobenzothiazole, and belongs to the technical field of organic chemistry. The method comprises the following steps: using 2-amino-6-chlorobenzothiazole as a raw material and acetonitrile as a solvent, adding copper chloride and isoamyl nitrite, carrying out a reaction to form a mixture of 2,6'-dichlorobenzothiazole and other impurities, and carrying out column chromatography separation to obtain pure 2,6'-dichlorobenzothiazole at a yield of 45-66%. The preparation method makes up for the deficiency of existing synthesis processes, andprovides a new method for synthesizing the 2,6'-dichlorobenzothiazole.

Description

technical field [0001] The invention relates to a preparation method of 2,6'-dichlorobenzothiazole, which belongs to the field of fine chemical intermediates. Background technique [0002] 2,6'-Dichlorobenzothiazole is an important intermediate in organic synthesis, mainly used in the fields of pesticides and dyes. It is a pesticide and herbicide thiazole for synthesizing aryloxyphenoxypropionate esters with high efficiency for controlling gramineous weeds. The key intermediate of diazopyl. [0003] At present, there are many methods for synthesizing 2,6'-dichlorobenzothiazole, and the common methods include 6-chlorobenzothiazole chlorination method, thiourea substitution method, p-chloroaniline and carbon disulfide and sulfur high pressure method, Hofmann's method for Chloro-o-aminothiophenol ring method, etc. However, many processes are not suitable for industrial production, such as harsh conditions such as high temperature and high pressure, high raw material costs, an...

Claims

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Application Information

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IPC IPC(8): C07D277/68
CPCC07D277/68
Inventor 王爱玲张腾崔颖娜王肖肖王帆郑学仿
Owner DALIAN UNIVERSITY
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