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Synthetic method of N-n-butyl-1,2-benzisothiazolin-3-ketone

A technology of benzisothiazoline and synthesis method, applied in directions such as organic chemistry, can solve the problems of high price, high price of anhydrous lithium iodide, difficulty in generating target products and the like

Inactive Publication Date: 2018-01-19
LIANYUNGANG SUNLION CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It is also reported that lithium iodide is used as a catalyst for the condensation product of BIT and substituted benzyl aromatic compounds (patent application number: 200910197261.6, applicant: Shanghai Pioneer Chemical Research Management Co., Ltd.), so that the O-generation structure product can be transformed into an N-generation structure , but anhydrous lithium iodide is expensive and the production cost is high
The Chinese patent No. 201410003853.0 is called a synthesis method of 2-butyl-1,2-benzisothiazolin-3-one, which uses o-methylthiobenzoic acid as a raw material and undergoes acyl chloride with an acyl chloride agent reaction, o-methylthiobenzoyl chloride is obtained, and then o-methylthiobenzoyl chloride is amidated with n-butylamine to obtain the corresponding amide compound, and finally the amide compound is reacted with a halogenating agent to obtain the target product 2 -Butyl-1,2-benzisothiazolin-3-one, although the generation of O-substituted derivatives has been avoided, the halogenating agent used in this patent is bromine, which is more expensive, and the last step of the ring-closing reaction Difficult to carry out, difficult to generate the target product

Method used

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  • Synthetic method of N-n-butyl-1,2-benzisothiazolin-3-ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach 1

[0031] Add 0.30mol of about 50.4g of dry o-methylthiobenzoic acid and 41g of thionyl chloride to 200ml of dichloroethane, raise the temperature to 60°C, react for a period of time, and analyze the unreacted o-methylthiobenzene by gas chromatography HPLC Acyl chloride reaction is completed when formic acid ≤0.50%. The solvent dichloroethane was removed to obtain 53.7 g of o-methylthiobenzoyl chloride, with a yield of 96.0%. The HPLC analysis product contained 99.54% o-methylthiobenzoyl chloride and 0.46% o-methylthiobenzoic acid.

[0032] Add 0.30mol about 55.9g of o-methylthiobenzoyl chloride to 300ml of dichloroethane, add dropwise a mixture of 50.4g of n-butylamine and 50g of dichloroethane at room temperature, and raise the temperature to 80°C for 2 hours after adding , add 18.5g of soda ash, 50g of water, distill and recover redundant n-butylamine and dichloroethane, wash with water and filter to obtain 63.2g of solid N-n-butyl-o-methylthiobenzamide. The HPLC analysis pr...

Embodiment approach 2

[0036] Add 0.34mol about 58.1g of dry o-methylthiobenzoic acid and 52g of thionyl chloride to 200ml of dichloroethane, raise the temperature to 61°C, react for a period of time, and analyze the unreacted o-methylthiobenzene by gas chromatography HPLC Acyl chloride reaction is completed when formic acid ≤0.50%. After removing the solvent, 62.1 g of o-methylthiobenzoyl chloride was obtained, with a yield of 96.3%. HPLC analysis product contains o-methylthiobenzoyl chloride 99.60%, o-methylthiobenzoic acid 0.39%.

[0037] Add 0.31mol about 58.4g of o-methylthiobenzoyl chloride to 300ml of dichloroethane, add dropwise a mixture of 52.4g of n-butylamine and 52g of dichloroethane at room temperature, and heat up to 82°C for 2.5 h, add 23.1 g of soda ash and 60 g of water, distill and recover excess n-butylamine and dichloroethane, wash with water, and filter to obtain 66.3 g of solid N-butyl-o-methylthiobenzamide. The HPLC analysis product contained N-n-butyl o-methylthiobenzamide...

Embodiment approach 3

[0041] Add 0.36mol of about 61.2g of dry o-methylthiobenzoic acid and 48g of thionyl chloride to 200ml of dichloroethane, raise the temperature to 62°C, react for a period of time, and analyze the unreacted o-methylthiobenzene by gas chromatography HPLC Acyl chloride reaction is completed when formic acid ≤0.50%. After removing the solvent, 64.3 g of o-methylthiobenzoyl chloride was obtained, with a yield of 94.7%. The HPLC analysis product contained 99.44% o-methylthiobenzoyl chloride and 0.55% o-methylthiobenzoic acid.

[0042] Add 0.33mol about 61.5g of o-methylthiobenzoyl chloride to 300ml of dichloroethane, add dropwise a mixture of 55.0g of n-butylamine and 55g of dichloroethane at room temperature, and heat up to 81°C for 2.2 h, add 24.5 g of soda ash and 75 g of water, distill and recover excess n-butylamine and dichloroethane, wash with water and filter to obtain 69.1 g of solid N-butyl-o-methylthiobenzamide. According to HPLC analysis, the product contained 99.06% ...

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Abstract

The invention relates to the field of chemical industry, and discloses a synthetic method of N-n-butyl-1,2-benzisothiazolin-3-ketone. The method comprises the following steps: S1) in an organic solvent, o-(methylthio) benzoic acid and an acyl chloride agent are subjected to a reaction to obtain o-(methylthio) benzoyl chloride; S2) the o-(methylthio) benzoyl chloride is dissolved in the organic solvent, a mixture of n-butylamine and the organic solvent is added and subjected to an amidation reaction to obtain N-n-butyl o-(methylthio) benzoyl chloride; S3) the N-n-butyl o-(methylthio) benzoyl chloride is dissolved in water, hydrogen peroxide is added, and the materials are subjected to an oxidation reaction to obtain N-n-butyl o-(methylthio) benzoyl chloride oxide; and S4) in the organic solvent, the N-n-butyl o-(methylthio) benzoyl chloride oxide and the acyl chloride agent are subjected to a ring-closure reaction to obtain the N-n-butyl-1,2-benzisothiazolin-3-ketone. The method can effectively avoid the generation of an O-substituted derivative, the ring-closure reaction is easily carried out, a target product is easily generated, and the cost is low.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a method for synthesizing N-n-butyl-1,2-benzisothiazolin-3-one. Background technique [0002] 1. Derivatives of 2-benzisothiazolin-3-one (hereinafter referred to as BIT) are generally H on the N atom replaced by alkyl-R or benzyl-CH 2 The products after Ar substitution reaction, the main varieties are: N-n-butyl-1, 2-benzisothiazolin-3-one (hereinafter referred to as BBIT), N-benzyl [o-chloro (bromo)-phenyl ]-1.2-benzisothiazolin-3-one, N-benzyl[m-chloro(bromine)-phenyl]-1.2-benzisothiazolin-3-one, N-benzyl[p-chloro(bromine) )-phenyl]-1.2-benzisothiazolin-3-one, N-benzyl (o-methoxy-phenyl)-1.2-benzisothiazolin-3-one, N-benzyl (m- Methoxy-phenyl)-1.2-benzisothiazolin-3-one, N-benzyl(p-methoxy-phenyl)-1.2-benzisothiazolin-3-one. [0003] Among them, BBIT is an oil-soluble broad-spectrum bactericide with bactericidal activity. It is used to protect polymers such as PVC, polyureth...

Claims

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Application Information

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IPC IPC(8): C07D275/04
Inventor 刘桂权
Owner LIANYUNGANG SUNLION CHEM
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