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Synthesis method of N-alkane-1, 2-benzisothiazoline-3-ketone

A technology of benzisothiazoline and synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of the first kind of raw materials, such as many kinds of raw materials, long process route, complicated process, etc., so as to reduce the environmental protection pressure of enterprises, reduce process difficulty and process flow. concise effect

Active Publication Date: 2021-04-09
安徽屹墩科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The first raw material in the prior art has many types and is more expensive, the process route is long, the process is complicated, the difficulty is high, and the yield of the product is low
[0004] The second one in the prior art uses an aprotic polar solvent as the medium, and the solvent cannot be recycled due to the influence of impurities, resulting in a large amount of waste liquid, and in actual production, the organic solvent has certain safety risks, and the product yield The rate is also low; in addition, the raw material 1,2-benzisothiazolin-3-one sodium salt is expensive, which is not conducive to the cost control of the product

Method used

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Examples

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preparation example Construction

[0024] The invention discloses a synthesis method of N-alkane-1,2-benzisothiazolin-3-one, which comprises the following steps,

[0025] (1) under nitrogen protection, 1mol phenylsulfur chloride is mixed and stirred with solvent;

[0026] (2) Control the temperature to 10-30° C., and add 1 mol of alkylcarbamoyl chloride dropwise;

[0027] (3) Slowly heat up to 60-80°C, hydrogen chloride is released, the system changes from clear to turbid, then becomes clear again, and a mixture is obtained;

[0028] (4) Mix and stir 1-1.2mol catalyst and solvent, keep warm to 40-60°C, and add the above mixture dropwise;

[0029] (5) After the dropwise addition, the system was heated up to 90° C. and kept for 2 hours until the residual BIT intermediate detected by HPLC was below 0.5%.

[0030] (6) Cool the system to 30-40°C, add water under stirring, let stand to separate layers, and obtain N-alkane-1,2-benzisothiazolin-3-one after vacuum distillation of the upper organic layer. The yield 90...

example 1

[0037] Under nitrogen protection, 144.5g of phenylsulfur chloride and 200g of chlorobenzene were mixed and stirred. Control the temperature at 15-20°C, add 135.5g of butylcarbamoyl chloride dropwise; slowly raise the temperature to 60-80°C, hydrogen chloride is released, the system turns from clear to turbid, and then becomes clear again to obtain a mixture.

[0038] Mix and stir 160g of anhydrous aluminum trichloride and 200g of chlorobenzene, keep warm at 40-60°C, and add the above mixture dropwise. After the dropwise addition was completed, the temperature of the system was raised to 90° C. and kept for 2 hours, and the residual intermediate was detected by HPLC to be below 0.5%. Cool down to 30-40°C, add 300g of water under stirring, stand to separate layers, and distill the upper organic layer under reduced pressure to obtain 193g of N-butyl-1,2-benzisothiazolin-3-one (BBIT), yield 93 %, the content is greater than 98%.

example 2

[0040] Under nitrogen protection, 144.5g of phenylsulfur chloride and 200g of chlorobenzene were mixed and stirred. Control the temperature at 15-20°C, add 93.5g of methylcarbamoyl chloride dropwise; slowly raise the temperature to 60-80°C, hydrogen chloride is released, the system turns from clear to turbid, and then becomes clear again to obtain a mixture.

[0041] Mix and stir 150g of anhydrous zinc chloride and 200g of chlorobenzene, keep warm at 40-60°C, and add the above mixture dropwise. After the dropwise addition was completed, the temperature of the system was raised to 90° C. and kept for 2 hours, and the residual intermediate was detected by HPLC to be below 0.5%. Cool down to 30-40°C, add 300g of water under stirring, let stand to separate layers, and distill the upper organic layer under reduced pressure to obtain 152g of N-methyl-1,2-benzisothiazolin-3-one (MBIT), yield 92 %, the content is greater than 98%.

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PUM

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Abstract

The invention discloses a synthetic method of N-alkane-1,2-benzisothiazoline-3-ketone, which comprises the following steps: (1) under the protection of nitrogen, mixing and stirring phenyl sulfur chloride and a solvent; (2) dropwise adding alkyl carbamyl chloride; (3) slowly heating until hydrogen chloride is released and the system becomes turbid from clear and then becomes clear again; (4) mixing and stirring a catalyst and the solvent, keeping the temperature, and dropwise adding the mixture; (5) after dropwise adding, heating the system to 90 DEG C, keeping the temperature for 2 hours, and detecting that the BIT intermediate residue is less than 0.5% by HPLC; and (6) cooling to 30-40 DEG C, adding water while stirring, standing for layering, and carrying out reduced pressure distillation on the upper organic layer to obtain the N-alkane 1, 2-benzisothiazoline-3-ketone. The method has the advantages of cheap raw materials, low process difficulty, simple process flow, less wastewater amount, high yield, less solid waste, environmental friendliness and the like.

Description

technical field [0001] The invention belongs to the field of chemical industry, in particular to a synthesis method of N-alkane-1,2-benzisothiazolin-3-one. Background technique [0002] There are mainly two types of prior art processes, one is to use 2-methylmercaptobenzoic acid as a raw material to prepare N-alkyl-1,2-benzisothiazolinone through acylation, alkylamination, and chlorination ring closure ; The other is 1,2-benzisothiazolin-3-ketone sodium salt as a raw material, in the aprotic polar solvent DMF, DMSO, etc., carry out N-alkylation with an alkylating agent to obtain N- Alkyl-1,2-benzisothiazolinones. [0003] The first kind of raw material in the prior art has many kinds and is relatively expensive, and the process route is long, the process is complicated, the difficulty is high, and the yield of the product is low. [0004] The second type in the prior art uses an aprotic polar solvent as the medium, and the solvent cannot be recycled due to the influence of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D275/04
CPCC07D275/04Y02P20/584
Inventor 江以桦杨采风谢渊吴家福
Owner 安徽屹墩科技股份有限公司