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

A technology of dioxole and chloromethyl, which is applied in the field of drug synthesis, can solve the problems of increasing the difficulty of environmental protection and high irritation, and achieve the effects of low difficulty in wastewater treatment, simple operation and high yield

Active Publication Date: 2022-05-06
SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Refluxing is required in the dropwise reaction stage. Excessive use of sulfuryl chloride will produce a large amount of hydrochloric acid and sulfur dioxide gas, which is highly irritating. It is necessary to carry out rearrangement reaction after removing the solvent by vacuum distillation, which will increase the difficulty of environmental protection.

Method used

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

Examples

Experimental program
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Embodiment 1

[0034] Put 50gDMDO and 300mL toluene into a dry three-necked flask, and stir evenly; at 0-10°C, add 87.3g of phosphorus oxychloride dropwise into the three-necked flask, and control the dropping time for 1.5h. Insulate at ℃ for 1h; heat up to 90°C and reflux, keep the temperature for 5h, cool to room temperature, and obtain the reaction product; the reaction product is stirred and washed with 3wt.% potassium carbonate aqueous solution, and the organic phase is separated with a separatory funnel after washing, and washed several times in this way Until the pH of the mixed solution is neutral, the washed organic phase is obtained; the washed organic phase is distilled off under reduced pressure to remove the solvent, and distilled at 91-93° C. under a vacuum of 2 mmHg to obtain 65.1 g of DMDO-Cl as a colorless liquid. Product purity 99.412%, yield 85.7%, see HPLC figure figure 1 , see Table 1 for HPLC data.

[0035] The HPLC data table of table 1 embodiment 1

[0036] ...

Embodiment 2

[0038] Put 50gDMDO and 400mL toluene into a dry three-necked flask, and stir evenly; at 10-20°C, add 80.5g of phosphorus oxychloride dropwise into the three-necked flask, and control the dropping time for 1h. After the dropwise addition, 10-20°C Keep warm for 0.5h; heat up to 100°C to reflux, keep warm for 6h, cool to room temperature, and get the reaction product. The reaction product was stirred and washed with 5wt.% potassium carbonate aqueous solution, and after washing, the organic phase was separated with a separatory funnel, and washed several times in this way until the pH of the mixed solution was neutral, and the washed organic phase was obtained. The washed organic phase was distilled off under reduced pressure to remove the solvent, and distilled at 91-93° C. under a vacuum of 2 mmHg to obtain a colorless liquid of DMDO-Cl. Product purity 99.368%, yield 82.5%, see HPLC figure figure 2 , see Table 2 for HPLC data.

[0039] The HPLC data table of table 2 embodimen...

Embodiment 3

[0042] Put 50gDMDO and 300mL toluene into a dry three-necked flask, and stir evenly; at 25-35°C, add 73.9g of phosphorus oxychloride dropwise into the three-necked flask, and control the dropping time for 1h, after the dropwise addition is completed, 25-35°C Keep warm for 0.5h; heat up to 110°C to reflux, keep warm for 4h, cool to room temperature, and get the reaction product. The reaction product was stirred and washed with 1wt.% potassium carbonate aqueous solution, and after washing, the organic phase was separated with a separatory funnel, and washed several times in this way until the pH of the mixed solution was neutral, and the washed organic phase was obtained. The washed organic phase was distilled off under reduced pressure to remove the solvent, and distilled at 91-93° C. under a vacuum of 2 mmHg to obtain a colorless liquid of DMDO-Cl. Product purity 99.129%, yield 81.2%, see HPLC figure image 3 , see Table 3 for HPLC data.

[0043] The HPLC data table of table...

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Abstract

The invention belongs to the technical field of medicine synthesis, and particularly relates to a preparation method of 4-chloromethyl-5-methyl-1, 3-dioxole-2-ketone. The preparation method comprises the following steps: mixing DMDO with methylbenzene, and then adding phosphorus oxychloride to react, so as to obtain the 4-chloromethyl-5-methyl-1, 3-dioxole-2-ketone. The process method is safe, reliable, simple and convenient to operate and suitable for industrial production, the product purity is 98% or above, the yield is high, and the wastewater treatment difficulty is low.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a preparation method of 4-chloromethyl-5-methyl-1,3-dioxol-2-one. Background technique [0002] 4-Chloromethyl-5-methyl-1,3-dioxol-2-one (DMDO-Cl), as an important pharmaceutical intermediate, can be used in olmesartan medoxomil, azil Tan ester, ampicillin and other synthesis. [0003] At present, the synthesis route of DMDO-Cl mainly uses 4,5-dimethyl-1,3-dioxol-2-one (DMDO) as the starting material, and the intermediate product is obtained by replacing chlorine with chlorinating reagent. The rearrangement reaction generates DMDO-Cl. The chlorination reagents reported in the relevant data include chlorine gas, sulfuryl chloride, NCS, etc. As a highly toxic gas, chlorine gas has potential safety hazards during use; sulfuryl chloride will generate sulfur dioxide gas after the reaction, which increases the difficulty of environmental protection; while usin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/40
CPCC07D317/40
Inventor 侯卫王书娟石友娟贾万水张明明
Owner SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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