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Preparation method for 4-chloromethyl-5-methyl-1,3-dioxol-2-one

A technology of dioxole and chloromethyl, applied in the direction of organic chemistry, can solve the problems of difficult separation of products and low rearrangement rate, and achieve the effects of increased yield, high conversion rate and high quality

Active Publication Date: 2018-04-10
濮阳天源生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When using DMDO and sulfuryl chloride or sulfuryl chloride or thionyl chloride or thionyl chloride to rearrange after chlorination to prepare DMDO-Cl, in this process, DMDO needs to be rearranged to obtain the product DMDO-Cl after chlorination. The rearrangement rate is low, and the product DMDO-Cl is difficult to separate from the product before rearrangement

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] A preparation method of 4-chloromethyl-5-methyl-1,3-dioxol-2-one, comprising the following steps:

[0025] Step 1: Preparation of DMDO:

[0026] Add 200g of acetoin, 350g of N,N-dimethylaniline, and 1,500g of dichloroethane into the three-necked flask while stirring, and then uniformly add 500g of methyl chloroformate dropwise. The reaction temperature is controlled at 0°C, and the reaction time is 5h. After completion, DMDO180g was obtained through precipitation;

[0027] Step 2: Preparation of DMDO-Cl:

[0028] Add 1500g of dichloroethane, 450g of N-chlorosuccinimide and 14.4g of benzoyl peroxide to the prepared DMDO while stirring, the reaction temperature is 100°C, and the reaction time is 5h to obtain 151g of crude DMDO-Cl , the yield is 83.89%;

[0029] Step 3: Distillation:

[0030] The crude DMDO-Cl was distilled at 100°C under a vacuum of -0.1MPa to obtain 126 g of refined DMDO-Cl, the purity of which was detected by gas chromatography was 99.65%.

Embodiment 2

[0032] A preparation method of 4-chloromethyl-5-methyl-1,3-dioxol-2-one, comprising the following steps:

[0033] Step 1: Preparation of DMDO:

[0034] Add 200g of acetoin, 200g of N,N-dimethylaniline, and 600g of dichloroethane into the three-necked flask while stirring, and then uniformly add 200g of ethyl chloroformate dropwise. The reaction temperature is controlled at -10°C, and the reaction time is 10h. After the reaction was completed, DMDO150g was obtained through precipitation;

[0035] Step 2: Preparation of DMDO-Cl:

[0036] Add 900g of methylene chloride, 225g of N-chlorosuccinimide and 7.5g of benzoyl peroxide to the DMDO obtained by stepping up while stirring, the reaction temperature is 30°C, and the reaction time is 10h to obtain 120g of DMDO-Cl crude product. The yield is 80%;

[0037] Step 3: Distillation:

[0038] The crude product of DMDO-Cl was distilled at 90°C under a vacuum of -0.1MPa to obtain 106 g of refined product DMDO-Cl, the purity of which w...

Embodiment 3

[0040] A preparation method of 4-chloromethyl-5-methyl-1,3-dioxol-2-one, comprising the following steps:

[0041] Step 1: Preparation of DMDO:

[0042] Add 200g of acetoin, 600g of N,N-dimethylaniline, and 2000g of dichloromethane into the three-necked flask while stirring, and then uniformly add 600g of propyl chloroformate dropwise. The reaction temperature is controlled at 20°C, and the reaction time is 0.5h. After completion, DMDO190g was obtained through precipitation;

[0043] Step 2: Preparation of DMDO-Cl:

[0044] Add 2850g of dichloromethane, 570g of N-chlorosuccinimide and 28.5g of azobisisobutyronitrile to the prepared DMDO while stirring. The reaction temperature is 150°C and the reaction time is 0.5h to obtain the crude product of DMDO-Cl 158g, yield is 83.16%;

[0045] Step 3: Distillation:

[0046] The crude product of DMDO-Cl was distilled at 130°C under a vacuum of -0.1 MPa to obtain 130 g of refined product DMDO-Cl, the purity of which was detected by ga...

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PUM

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Abstract

The invention specifically relates to a preparation method for 4-chloromethyl-5-methyl-1,3-dioxol-2-one, belonging to the technical field of chemical synthesis. According to the invention, acetoin isused as a raw material and reacts with chloroformate in a solvent under the action of a catalyst so as to produce DMDO; the prepared DMDO is further reacts with a chlorinating reagent and a free radical initiator in a solvent to obtain a crude DMDO-Cl product; and then rectification is carried out so as to obtain a fine DMDO-Cl product. The fine DMDO-Cl product has a purity of 99% or above.

Description

technical field [0001] The invention belongs to the technical field of chemical 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 for short, CAS No. 80841-78-7, 4,5-Dimethyl-1,3 -Dioxol-2-one, referred to as DMDO, is an intermediate for the synthesis of DMDO-Cl, and can also be sold as a product, CAS No. 37830-90-3. The main use of the two substances is pharmaceutical intermediates, which are used in the synthesis of lenamcillin and olmesartan, and can also be used in other penicillins, cephalosporins, atypical lactams and β-lactamase inhibitors Synthesis of drugs, antihypertensives and other drugs. [0003] In the prior art, when using acetoin and phosgene or diphosgene or triphosgene to react to prepare DMDO, phosgene or diphosgene or triphosgene itself or the products after decomposition are highly toxic gases, and the operation risk is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/40
CPCC07D317/40
Inventor 赵军侠文教刚王利霞吕孝永付敬超刘仁欢陈永装王丽娜
Owner 濮阳天源生物科技有限公司
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