Method for synthesizing N-substitued benzo-isothiazolone derivative

The technology of a kind of benzisothiazolinone and synthetic method is applied in the field of synthesis of N-substituted benzisothiazolinone derivatives, which can solve the problems of low yield of derivatives, low utilization rate of raw materials, easy water absorption and deliquescence, etc. Achieve high yield, stable product quality, and improve reaction selectivity

Inactive Publication Date: 2014-12-24
SHANGHAI CHEM REAGENT RES INST
View PDF4 Cites 10 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The technical problem to be solved by this invention is to provide a kind of synthetic method of N-substituted benzisothiazolinone derivatives, to overcome the prior art need to use chlorinated chlorinated chlorinated acid with strong irritant, easy to absorb water and deliquescence, and low utilization rate of raw materials. Sulfone is acylated to produce acid chloride, bromine is used to break the disulfide bond, and the cyclization reaction generates corrosive hydrogen bromide. The shortcoming of the low yield of derivatives with long-chain N substituents is produced by kettle reaction.

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
  • Method for synthesizing N-substitued benzo-isothiazolone derivative
  • Method for synthesizing N-substitued benzo-isothiazolone derivative
  • Method for synthesizing N-substitued benzo-isothiazolone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Step 1): Add 59.4g (0.2mol) triphosgene, 100g xylene, 6.1g (0.06mol) three Ethylamine, stir to dissolve, control the system temperature at -5~5°C, dissolve 91.8g (0.3mol) 2,2'-dithiodibenzoic acid in 200g xylene, and then drop it slowly and uniformly into the above-mentioned triphosgene In the mixed solution, the dropping time was controlled at 2 hours, then the temperature was raised to 100°C, the reaction was stirred for 3 hours, and 86.6 g of 2,2'-dithiodibenzoyl chloride was obtained by distillation under reduced pressure, with a yield of 84.2% and a purity of 98.4 %.

[0036] Step 2): Add 63.0g (0.6mol) aniline, 120ml xylene, 50.5g (0.5mol) triethylamine in a 500ml four-neck reaction flask equipped with a thermometer, agitator, reflux condenser, and constant pressure funnel Amine, stir to dissolve, control the temperature of the system at -5 ~ 5 ° C, slowly and uniformly drop into 150ml xylene solution dissolved with 86.6g (0.25mol) 2,2'-dithiodibenzoyl chloride, ...

Embodiment 2

[0039] Step 1): Add 59.4g (0.2mol) triphosgene, 150g chlorobenzene, 2.4g (0.03mol) pyridine to a 500ml four-necked reaction flask equipped with a thermometer, agitator, reflux condenser, and constant pressure funnel , stir to dissolve, control the system temperature at -5-5°C, dissolve 91.8g (0.3mol) 2,2'-dithiodibenzoic acid in 220g chlorobenzene, and then drop it slowly and uniformly into the above-mentioned triphosgene mixed solution , the dropping time was controlled at 2 hours, then the temperature was raised to 110°C, the reaction was stirred for 3 hours, and 89.2 g of 2,2'-dithiodibenzoyl chloride was obtained by distillation under reduced pressure, with a yield of 86.7% and a purity of 98.9%.

[0040]Step 2): Add 79.6g (0.624mol) 4-chloroaniline, 120ml xylene, 41.1g (0.52mol ) pyridine, stir to dissolve, control the temperature of the system at 0-5°C, slowly and uniformly drop into 150ml xylene solution dissolved with 89.2g (0.26mol) 2,2'-dithiodibenzoyl chloride, and ...

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 discloses a method for synthesizing an N-substitued benzo-isothiazolone derivative. The method comprises the following steps: using 2, 2'-dithiodibenzoic acid and triphosgene as raw materials to carry out acylating chlorination, reacting 2, 2'-dithiodibenzoyl chloride with an amine compound to obtain an amide compound, and then performing disproportionation cyclization reaction on the amide compound and an oxidant in a micro-channel reactor under alkaline conditions to obtain the N-substitued benzo-isothiazolone derivative. The synthesizing method has the advantages of 98% above selectivity, 62% above raw material conversion rate, 54% above yield rate, 99% above product purity, strong technical path operability, safe and simple operation process, stable product quality and high yield rate and is suitable for industrial production.

Description

technical field [0001] The invention relates to a synthesis method of N-substituted benzisothiazolinone derivatives. Background technique [0002] Isothiazolinone compounds are a new type of high-efficiency broad-spectrum fungicides, which have the advantages of high efficiency, low toxicity, long duration of efficacy, and environmental safety, so they are widely developed and used in medicine, pesticides and industrial fields. Because these compounds have good algicidal and antibacterial activities, they also have broad application prospects in green marine antifouling agents. [0003] There are few reports on the synthesis of N-substituted benzisothiazolinone derivatives at home and abroad, and the current reports are all laboratory synthesis methods, while industrial production processes have not been reported yet. There are mainly three routes in the existing laboratory synthesis methods. All three routes use 2,2'-dithiodibenzoic acid as raw material. [0004] Route 1...

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 张传好李海涛周艳蒋旭亮
Owner SHANGHAI CHEM REAGENT RES INST
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap