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Chemosynthesis method of 4-chloromethyl-5-methyl-1,3-dioxy heterocyclic pentene-2-ketone

A technology of dioxolene and chloromethyl, which is applied in the field of chemical synthesis of 4-chloromethyl-5-methyl-1,3-dioxol-2-one, can solve industrial Problems such as low application value, high toxicity of chlorine gas, and low reaction yield, etc., to achieve high implementation value and social and economic benefits, less three wastes, and high total reaction yield

Inactive Publication Date: 2008-08-27
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the low reaction yield of chlorine gas and the high toxicity of chlorine gas, there are also great safety problems in the application
And N-chlorosuccinimide method yield is also very low, and cost is high
Therefore, these two methods have the disadvantages of low industrial application value.

Method used

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  • Chemosynthesis method of 4-chloromethyl-5-methyl-1,3-dioxy heterocyclic pentene-2-ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] The molar ratio of the feed material is: DMDO: sulfuryl chloride is 1: 1.05. The organic solvent is dichloromethane, the amount of which is 7 times the mass of DMDO; the rearrangement temperature is 90°C.

[0017] Add 300ml of dichloromethane and 60g of DMDO to a 500ml four-neck flask equipped with a mechanical stirrer, a constant pressure dropping funnel, a reflux condenser and a thermometer and a tail gas absorption device, and start to heat up to reflux. Then 74.6 g of sulfuryl chloride was added dropwise for about 2 hours. After dripping, keep it warm for 2 hours under the same conditions, then remove the solvent by rotary evaporation, and rearrange the product after removal of the solvent at 90°C for 2 hours to obtain a crude reaction product, which is separated by rectification to obtain 58.2 g of the product. The yield is 74.5%, and the purity is 98.5%.

[0018] Structure Characterization:

[0019] IR: v max / cm -1 : 1820.4 (C=O), 1733.8 (C=O).

[0020] 1 ...

Embodiment 2

[0022] The molar ratio of the feed material is: DMDO: sulfuryl chloride is 1: 1.05. The organic solvent is dichloromethane, the amount of which is 7 times the mass of DMDO; the rearrangement temperature is 90°C.

[0023] Add 300ml of dichloromethane and 60g of DMDO to a 500ml four-neck flask equipped with a mechanical stirrer, a constant pressure dropping funnel, a reflux condenser and a thermometer and a tail gas absorption device, and start to heat up to reflux. Then 74.6 g of sulfuryl chloride was added dropwise for about 3 hours. After dripping, the reaction was incubated under the same conditions for 1 hour, and then the solvent was removed by rotary evaporation, and the solvent-removed product was rearranged at 90° C. for 4 hours to obtain a crude reaction product. Separation by rectification gave 54.5 g of a colorless product, 4-chloromethyl-5-methyl-1,3-dioxol-2-one, with a yield of 69.7% and a purity of 96.8%.

Embodiment 3

[0025] The molar ratio of the feed material is: DMDO: sulfuryl chloride is 1: 1.05. The organic solvent is dichloromethane, the amount of which is 7 times the mass of DMDO; the rearrangement temperature is 90°C.

[0026] Add 300ml methylene chloride and 60g DMDO to a 500ml four-neck flask equipped with a constant pressure dropping funnel, a reflux condenser and a thermometer and a tail gas absorption device, and start to heat up to reflux. Then 74.6 g of sulfuryl chloride was added dropwise for about 1 hour. After dripping, the reaction was incubated under the same conditions for 3 hours, then the solvent was removed by rotary evaporation, and the solvent-removed product was rearranged at 90° C. for 2 hours to obtain a crude reaction product. Separation by rectification gave 55.3 g of light yellow product 4-chloromethyl-5-methyl-1,3-dioxol-2-one with a yield of 70.8% and a purity of 97.6%.

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Abstract

The invention provides a chemical synthesis method of 4-chloromethyl-5-methyl-1, 3-dioxa cyclopentene-2-ketone, which comprises using 4, 5-dimethyl-1, 3-dioxa cyclopentene-2-ketone as raw material and uses sulfuryl chloride as chlorinating agent to process reflux reaction in organic solvent for 1-3h, evaporating out the solvent, rearranging for 1-4h at 70-100DEG C, and separating the reaction liquor after the rearrangement to obtain the 4-chloromethyl-5-methyl-1, 3-dioxa cyclopentene-2-ketone. The chemical synthesis method has the advantages of reasonable process conditions, reliable and safe production, high reaction total yield, low production cost, little discharge of three wastes and significant pratical, social and economic benefits.

Description

(1) Technical field [0001] The present invention relates to a kind of chemical synthesis method of 4-chloromethyl-5-methyl-1,3-dioxol-2-one, especially a kind of 4,5-dimethyl-1, Preparation of 4-chloromethyl-5-methyl-1,3-dioxol-2 from 3-dioxol-2-one (DMDO) using sulfuryl chloride as the chlorination reagent - Chemical synthesis of ketones. (2) Background technology [0002] 4-Chloromethyl-5-methyl-1,3-dioxol-2-one is mainly used in the synthesis of new semi-synthetic antibiotics, such as for the synthesis of semi-synthetic penicillins——Lenampicillin Hydrochloride, etc. ). [0003] Prior to the present invention, the main existing method for the chemical synthesis of 4-chloromethyl-5-methyl-1,3-dioxol-2-one was from chlorine gas or N-chlorosuccinimide Obtained by chlorination reaction, such as Tetrahedron Letters, 1972, 170-1704, USP 4428806, JP 6010571, US 4448732, etc. Due to the low reaction yield of chlorine gas and the high toxicity of chlorine gas, there are also gr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/40
Inventor 俞传明苏为科谢媛媛何人宝王莺妹钟建新
Owner ZHEJIANG UNIV OF TECH
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