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
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  • 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

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0023] Example 1:

[0024] The present embodiment provides a purification method for 4-chloromethyl-5-methyl-1,3-dioxol-2-one (namely DMDO-Cl), and the specific operations are as follows:

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

[0026] Add 50.0g of 4,5-dimethyl-1,3-dioxol-2-one and 530g of dichloromethane to a 1L four-necked flask, stir to dissolve, heat up and reflux, and the internal temperature is not lower than 40 At ℃, dropwise add 65g (1.1 equiv) of sulfonyl chloride and 132g of dichloromethane mixture, control the internal temperature to be no less than 40℃, keep stirring for 2h after dropping, then heat up to 85℃ while distilling off dichloromethane. When reaching 85 ℃, rearrangement is carried out for 2 to 3 hours. Drop to room temperature to obtain crude DMDO-Cl with a GC purity of 85% to 90%.

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

Example Embodiment

[0030] Example 2:

[0031] The present embodiment provides a purification method for 4-chloromethyl-5-methyl-1,3-dioxol-2-one (namely DMDO-Cl), and the specific operations are as follows:

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

[0033] Add 50.0g of 4,5-dimethyl-1,3-dioxol-2-one and 530g of dichloromethane to a 1L four-necked flask, stir to dissolve, heat up and reflux, and the internal temperature is not lower than 40 At ℃, dropwise add 65g (1.1 equiv) of sulfonyl chloride and 132g dichloromethane mixture, control the internal temperature to not be lower than 40℃, keep stirring for 2h after dropping, then heat up to 85℃ while distilling off dichloromethane. When reaching 90°C, rearrangement is carried out for 2-3h. Drop to room temperature to obtain crude DMDO-Cl with a GC purity of 85% to 90%.

[0034] Add 30ml of ethanol to the above crude product, stir and cool down to -10℃~-5℃, crystallize for 0~1.5h, suction filter, rinse with -5℃ ethanol to obtain 52.8g of ...

Example Embodiment

[0037] Example 3:

[0038] The present embodiment provides a purification method for 4-chloromethyl-5-methyl-1,3-dioxol-2-one (namely DMDO-Cl), and the specific operations are as follows:

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

[0040] Add 50.0g of 4,5-dimethyl-1,3-dioxol-2-one and 530g of dichloromethane to a 1L four-necked flask, stir to dissolve, heat up and reflux, and the internal temperature is not lower than 40°C , add dropwise a mixture of 65g (1.1 equiv) of sulfonyl chloride and 132g of dichloromethane, control the internal temperature to not be lower than 40°C, keep stirring for 2h after dropping, then heat up to 85°C while distilling off the dichloromethane. When reaching 85 ℃, rearrangement is carried out for 2 to 3 hours. Drop to room temperature to obtain crude DMDO-Cl with a GC purity of 85% to 90%.

[0041] Add 30 ml of isopropanol to the above crude product, stir and cool down to -10 ℃~-5 ℃, crystallize 0~1h, suction filter, rinse with isopropano...

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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

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Application Information

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