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

Purification method of 4-chloromethyl-5-methyl-1,3-dioxole-2-ketone

A dioxole and purification method technology, applied in the field of medicinal chemistry, can solve the problems of low production capacity, low DMDO-Cl yield, low purity, etc., and achieve the goals of reducing energy consumption, shortening production cycle, and simplifying production operations Effect

Active Publication Date: 2014-06-18
ZHEJIANG HUAHAI PHARMACEUTICAL CO LTD
View PDF3 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] What the present invention aims to solve are the technical deficiencies such as low yield, low purity and low production capacity in the industrial production of DMDO-Cl, and a purification method for DMDO-Cl is provided

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
  • Purification method of 4-chloromethyl-5-methyl-1,3-dioxole-2-ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] This embodiment provides a purification method of 4-chloromethyl-5-methyl-1,3-dioxol-2-one (i.e. DMDO-Cl), the specific operation is as follows:

[0025] (1) Preparation of crude DMDO-Cl

[0026] Add 50.0g of 4,5-dimethyl-1,3-dioxol-2-one and 530g of dichloromethane into a 1L four-neck flask, stir to dissolve, heat up to reflux, and the internal temperature is not lower than 40 At ℃, add a mixture of 65g (1.1 equivalent) of sulfuryl chloride and 132g of dichloromethane dropwise, control the internal temperature to not lower than 40℃, keep stirring for 2 hours after dropping, then raise the temperature to 85℃ and distill off the dichloromethane at the same time. When it reaches 85°C, rearrange for 2 to 3 hours. After cooling down to room temperature, the crude product of DMDO-Cl was obtained with a GC purity of 85%-90%.

[0027] Add 30ml of methanol to the above crude product, stir and cool down to -10°C ~ -5°C, crystallize for 0 ~ 3h, filter with suction, rinse with m...

Embodiment 2

[0031] This embodiment provides a purification method of 4-chloromethyl-5-methyl-1,3-dioxol-2-one (i.e. DMDO-Cl), the specific operation is as follows:

[0032] (1) Preparation of crude DMDO-Cl

[0033] Add 50.0g of 4,5-dimethyl-1,3-dioxol-2-one and 530g of dichloromethane into a 1L four-neck flask, stir to dissolve, heat up to reflux, and the internal temperature is not lower than 40 At ℃, add a mixture of 65g (1.1 equivalent) of sulfuryl chloride and 132g of dichloromethane dropwise, control the internal temperature not lower than 40℃, keep stirring for 2 hours after dropping, then raise the temperature to 85℃ and distill off the dichloromethane at the same time. When it reaches 90°C, rearrange for 2-3h. After cooling down to room temperature, the crude product of DMDO-Cl was obtained with a GC purity of 85%-90%.

[0034] Add 30ml of ethanol to the above crude product, stir and lower the temperature to -10°C to -5°C, crystallize for 0 to 1.5h, filter with suction, rinse wi...

Embodiment 3

[0038] This embodiment provides a purification method of 4-chloromethyl-5-methyl-1,3-dioxol-2-one (i.e. DMDO-Cl), the specific operation is as follows:

[0039] (1) Preparation of crude DMDO-Cl

[0040] Add 50.0g of 4,5-dimethyl-1,3-dioxol-2-one and 530g of dichloromethane into a 1L four-neck flask, stir to dissolve, heat up to reflux, and the internal temperature is not lower than 40°C 65g (1.1 equivalent) of sulfuryl chloride and 132g of dichloromethane were added dropwise, and the internal temperature was controlled not to be lower than 40°C. After the dropping was completed, the mixture was kept warm and stirred for 2 hours, and then the temperature was raised to 85°C while distilling off the dichloromethane. When it reaches 85°C, rearrange for 2 to 3 hours. After cooling down to room temperature, the crude product of DMDO-Cl was obtained with a GC purity of 85%-90%.

[0041] Add 30ml of isopropanol to the above crude product, stir and lower the temperature to -10°C to -...

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

PropertyMeasurementUnit
Boiling pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Login to View More

Abstract

The invention discloses a purification method of 4-chloromethyl-5-methyl-1,3-dioxole-2-ketone. The purification method comprises the following steps of dissolving a crude product of 4-chloromethyl group-5-methyl-1,3-dioxole-2-ketone into a mixed solvent of methyl alcohol, ethyl alcohol, isopropyl alcohol and tertiary butanol for crystallizing for 0-24 hours at a temperature of -10-0 DEG C, and filtering to acquire the 4-chloromethyl-5-methyl-1,3-dioxole-2-ketone. The purification method has the characteristics of low cost, good refining effect, high yield, low requirement on equipment and simplicity and convenience in operation and is suitable for industrial production.

Description

technical field [0001] The invention relates to a purification method of 4-chloromethyl-5-methyl-1,3-dioxol-2-one (DMDO-Cl), belonging to the field of medicinal chemistry. Background technique [0002] 4-Chloromethyl-5-methyl-1,3-dioxol-2-one (DMDO-Cl) is an important intermediate for the synthesis of drugs such as lenamcillin and olmesartan medoxomil. The research on its purification method has important economic value and significance, and its synthetic route is as follows: [0003] [0004] US4554358, US4448732, USP4428806, JP6010571, etc. disclose a 4-chloro-4-methyl-5- Methylene-5-methylene-1,3-dioxolane-2-one, after rearrangement reaction at 90°C, produces crude DMDO-Cl, which is distilled at 91-93°C and 2mmHg to obtain DMDO-Cl, but It is difficult to achieve a vacuum degree of 2 mmHg in industry, and DMDO-Cl is prone to decomposition and polymerization at high temperature and deteriorates, and the yield is low. It is also reported in the literature that the puri...

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
IPC IPC(8): C07D317/40
CPCC07D317/40
Inventor 王集权李国祥熊学强
Owner ZHEJIANG HUAHAI PHARMACEUTICAL CO LTD
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