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

Method for catalyzed synthesis of high-purity 4-chloromethyl-5-methyl-1,3-dioxol-2-one

A technology of dioxole and synthesis method, applied in chemical instruments and methods, physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, etc., can solve the problem of reducing industrial application value, difficult to Separation, impure products and other problems, to achieve the effect of large implementation value and social and economic benefits, safe and reliable production, and low production cost

Active Publication Date: 2013-12-18
HEFEI UNIV OF TECH
View PDF2 Cites 16 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But this reaction can generate dichloro-adduct 4,5-dichloro-4,5-dimethyl-1,3-dioxolan-2-one, which is difficult to completely separate from the target product, so although The operation is simple, but the product is impure, which reduces its industrial application value

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 catalyzed synthesis of high-purity 4-chloromethyl-5-methyl-1,3-dioxol-2-one
  • Method for catalyzed synthesis of high-purity 4-chloromethyl-5-methyl-1,3-dioxol-2-one

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] 1. Raw material and ratio

[0031] The molar ratio of the feed material is: DMDO:sulfonyl chloride is 1:1.5.

[0032] The catalyst is phenyl selenium chloride, and the molar weight of the catalyst is 5% of the molar weight of DMDO.

[0033] Organic solvent is dichloromethane, and its quality consumption is 7 times of DMDO quality.

[0034] 2. Preparation

[0035] Add 300ml of dichloromethane, 60g of DMDO and 5mol% of phenyl selenium chloride to a 500ml three-necked flask equipped with magnetic stirring, a constant pressure dropping funnel and an exhaust gas absorption device, and slowly add 106.6g of sulfonyl chloride dropwise while stirring , added dropwise for about 3 hours, reacted at room temperature for 2 hours after the dropwise addition, and removed the solvent by rotary evaporation to obtain 65.9 g of the target product with a yield of 84.4% and a purity of 98.9%.

[0036] Structure Characterization:

[0037] IR: ν max / cm -1 : 3026 (C-H), 1694 (C=C), 715 ...

Embodiment 2

[0039] 1. Raw material and ratio

[0040] The molar ratio of the feed material is: DMDO:sulfonyl chloride is 1:1.5.

[0041] The catalyst is p-methylphenyl selenium chloride, and the molar weight of the catalyst is 5% of the molar weight of DMDO.

[0042] Organic solvent is dichloromethane, and its quality consumption is 7 times of DMDO quality.

[0043] 2. Preparation

[0044] Add 300ml of dichloromethane, 60g of DMDO and 5mol% p-methylphenylselenium chloride into a 500ml three-necked flask equipped with magnetic stirring, a constant pressure dropping funnel and an exhaust gas absorption device, and slowly add 106.6 g sulfuryl chloride, added dropwise for about 3 hours, reacted at room temperature for 2 hours after the dropwise addition, and removed the solvent by rotary evaporation to obtain 53.8 g of the target product with a yield of 68.9% and a purity of 96.7%.

Embodiment 3

[0046] 1. Raw material and ratio

[0047] The molar ratio of the feed material is: DMDO:sulfonyl chloride is 1:1.5.

[0048] The catalyst is polystyrene-based selenium bromide, and the molar weight of the catalyst is 5% of the molar weight of DMDO.

[0049] Organic solvent is dichloromethane, and its quality consumption is 7 times of DMDO quality.

[0050] 2. Preparation

[0051] 1) Preparation of polystyrene-based selenium bromide

[0052] ① Disperse 5 grams (about 0.083 mmol) of polystyrene particles in 100 ml of cyclohexane, add 2 mmol of n-butyllithium and 2 mmol of tetramethylethylenediamine (TMEDA), react at 65 ° C for 4 hours, filter after the reaction and wash with tetrahydrofuran (THF) washing to obtain lithium-containing polystyrene;

[0053] ② Add 10.0 mmol dimethyl diselenide (MeSe-SeMe) and 100 ml THF to the lithium-containing polystyrene, and react at 0° C. for 30 min to obtain polystyrene with methyl selenium groups, which is a light yellow resin.

[0054] ...

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 catalyzed synthesis of high-purity 4-chloromethyl-5-methyl-1,3-dioxol-2-one. The method comprises the following steps: reacting 4,5-dimethyl-1,3-dioxol-2-one as a raw material with sulfonyl chloride as a chlorination reagent for 1-5 hours in an organic solvent under the effect of a catalyst; evaporating to remove the solvent after the reaction is ended, so as to obtain the target product 4-chloromethyl-5-methyl-1,3-dioxol-2-one. The preparation method disclosed by the invention is high in selectivity, one-step in reaction, free of by-product, high in reaction yield, safe and reliable to produce, simple to operate, low in production cost, and fewer in three wastes, and has great implement value and socioeconomic benefits.

Description

1. Technical field [0001] The invention relates to a method for catalytically synthesizing organic compounds, in particular to a method for catalytically synthesizing high-purity 4-chloromethyl-5-methyl-1,3-dioxol-2-one. 2. Background technology [0002] 4-Chloromethyl-5-methyl-1,3-dioxol-2-one is a very useful substitute for semi-synthetic penicillin esters such as lenampicillin and mecillin (Lenampicillin, Mecillinam), etc. Branched side chains are used to improve the stability and absorption of drugs, increase biological activity, and reduce side effects. It is also used to prepare amine drugs, such as Norfloxacin (Norfloxacin prodrug). [0003] In the prior art, the main method of synthesizing 4-chloromethyl-5-methyl-1,3-dioxol-2-ketone is formed by chlorine gas or N-chlorosuccinimide chlorination reaction. Obtained, for example Tetrahedron Letters, 1972, 170-1704, USP4428806, JP6010577, US4448732 etc. Due to the low reaction yield of the chlorine gas method and the h...

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): C07D317/40B01J31/06
Inventor 冯乙巳刘翠郝剑汪云龙毛龙汪鹏飞
Owner HEFEI UNIV OF TECH
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