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
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  • 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

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  • 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

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Experimental program
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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] ...

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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

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Application Information

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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
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