Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Novel synthesis method of 2-butyl-1,2-benzothiazol-3-one

A technology of isothioline and a new method, which is applied in the field of 2-butyl-1,2-benzisothiazolin-3-one synthesis, can solve the problems of poor selectivity, by-product generation, and large amount of three wastes, etc.

Active Publication Date: 2018-11-16
CHANGZHOU UNIV
View PDF2 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that toxic thionyl chloride reagent needs to be used, and a large amount of hydrogen chloride and sulfur dioxide waste gas produced by the reaction need to be treated, and the total yield of the target product is not higher than 65%, the yield is low, and the amount of three wastes is large
The disadvantage of this method is that the selectivity is poor, and a large number of by-products are produced, which makes it difficult to purify and separate the target product, and the total yield is about 65%.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Novel synthesis method of 2-butyl-1,2-benzothiazol-3-one
  • Novel synthesis method of 2-butyl-1,2-benzothiazol-3-one

Examples

Experimental program
Comparison scheme
Effect test

specific Embodiment 1

[0010] Add N-butyl-2-methylthiobenzamide (20mmol, 2.23g), 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2. 2] Octane bis(tetrafluoroborate) salt (20mmol, 3.55g) and 20mL of N,N-dimethylformamide, the reaction temperature was controlled at 60°C, and the reaction was vigorously stirred for 6h. After the reaction, cool to room temperature, wash the reaction system with water, extract, distill the filtrate under reduced pressure, and collect the main fraction to obtain 2-butyl-1,2-benzisothiazolin-3-one (3.80g, 92%).

[0011] The equations involved in the reaction are as follows:

[0012]

specific Embodiment 2

[0013] Add N-butyl-2-methylthiobenzamide (20mmol, 4.46g), 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2. 2] Octane bis(tetrafluoroborate) salt (20mmol, 7.10g) and 20mL of N,N-dimethylformamide, the reaction temperature was controlled at 40°C, and the reaction was vigorously stirred for 6h. After the reaction, cool to room temperature, wash the reaction system with water, extract, distill the filtrate under reduced pressure, and collect the main fraction to obtain 2-butyl-1,2-benzisothiazolin-3-one (3.40g, 82%).

[0014]

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to the technical field of fine chemical engineering, and discloses a novel synthesis method of 2-butyl-1,2-benzothiazol-3-one. The method comprises the following specific steps:allowing N-butyl-2-methyl(thiobenzamide) to react with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) in the presence of N,N-dimethyl-formamide for six hours at 60 DEGC, so as to obtain 2-butyl-1,2-benzothiazol-3-one. Compared with the prior art, the method has the advantages that no metal ions or chlorine-containing toxic reagents are introduced, and the yield ishigh, the operation is simple, the influence on the environment is small, the potential industrial value is achieved, and the method is worthy of popularization and application.

Description

technical field [0001] The invention belongs to the field of fine chemical industry and relates to a new synthesis method of 2-butyl-1,2-benzisothiazolin-3-one. Background technique [0002] 2-Butyl-1,2-benzisothiazolin-3-one (BBIT) is an important industrial and agricultural fungicide, widely used in plastics and other polymers and wood furniture and other antiseptic and bactericidal, so its research has been Widespread concern. At present, there are two common methods for synthesizing 2-butyl-1,2-benzisothiazolin-3-one: the first method, using dithiodibenzoic acid as raw material, after chlorination by thionyl chloride It reacts with n-butylamine to generate the corresponding amide, and then cyclizes by breaking the disulfide bond to obtain 2-butyl-1,2-benzisothiazolin-3-one. The disadvantage of this method is that toxic thionyl chloride reagent needs to be used, and a large amount of hydrogen chloride and sulfur dioxide waste gas produced by the reaction need to be trea...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D275/04
CPCC07D275/04
Inventor 杨科陈中淼张浩唐天地
Owner CHANGZHOU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com