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The preparation method of 5-ethylpyridine-2,3-dicarboxylate diethyl ester

A technology of diethyl diformate and diethyl chlorooxaloacetate, applied in the direction of organic chemistry and the like, can solve the problems of low yield of closed ring nitrogen sources, many three wastes, and high production cost, and achieves easy industrialization and application. Effect

Active Publication Date: 2015-11-04
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The purpose of the invention is to propose a new 5-ethylpyridine-2, the preparation method of 3-dicarboxylate, to overcome the three wastes of using ammonium sulfamate or hydroxylamine sulfate as the ring-closing nitrogen source in the prior art Many, high production costs, many unsafe factors and other disadvantages, as well as the problem of low yield of ammonia gas as the ring-closing nitrogen source, so as to meet the needs of industrial production

Method used

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Embodiment 1

[0034] Preparation of diethyl α-chlorooxaloacetate (referred to as oxychloro)

[0035] Add 15g of sodium ethoxide to 500g of toluene, stir evenly, raise the temperature to 40-45°C, add dropwise a mixture of 112.5g (0.75mol) of diethyl oxalate and 64.5g (0.5mol) of ethyl chloroacetate, wash after the reaction, and remove After dissolving, 108 g of oxychloride was obtained, and the analysis content was 85.6%.

[0036] Preparation of diethyl 5-ethylpyridine-2,3-dicarboxylate

[0037] Add 60g of ethanol and 19.4g (99%, 0.25mol) of ammonium acetate into a 500ml four-necked bottle, stir and raise the temperature to ethanol 75-80°C, after the reflux is stable, add 27g (85.6%, 0.1mol) of α-chlorooxalyl dropwise A mixed solution of diethyl acetate and 12.1g (97%, 0.14mol) 2-ethylacrolein, the reaction system is controlled to be in a reflux state during the dropwise addition, and after about 30 minutes of completion of the dropwise addition, it is kept at 75-80°C for 5-6 Hours to the ...

Embodiment 2

[0039] Add 53g of ethanol and 17.2g (99%, 0.22mol) of ammonium acetate into a 500ml four-necked bottle, stir and raise the temperature to ethanol 75-80°C, after the reflux is stable, add 27g (85.6%, 0.1mol) of α-chlorooxalyl dropwise A mixed solution of diethyl acetate and 8.7g (97%, 0.10mol) 2-ethylacrolein, the reaction system is controlled to be in a reflux state during the dropping process, and after about 30 minutes of dropping, keep warm at 75-80°C for 5-6 Hour to analysis showed complete reaction of diethyl α-chlorooxaloacetate. Aftertreatment is the same as example 1, obtains brownish yellow oily liquid 26.5g, and content (gas spectrum analysis) is 87.6%, 1HNMR and IR analysis confirmed its structure, and the yield was 92.5%.

Embodiment 3

[0041] Add 73g of ethanol and 15.6g (99%, 0.2mol) of ammonium acetate into a 500ml four-neck bottle, stir and heat up to 75-80°C of ethanol, after the reflux is stable, add 27g (85.6%, 0.1mol) of α-chlorooxalyl dropwise Mixed solution of diethyl acetate and 8.7g (97%, 0.10mol) 2-ethylacrolein, control the reaction system to reflux state during the dropwise addition process, after about 30min dropwise addition, keep warm at 75-80°C for 5-6 hours until the reaction is complete. Aftertreatment is the same as example 1, obtains brownish yellow oily liquid 25.8g, and content (gas spectrum analysis) is 90.6%, 1 HNMR and IR analysis confirmed its structure, and the yield was 91.7%.

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Abstract

The invention belongs to the field of organic synthesis and discloses a preparation method of 5-ethylpyridine-2,3-diethyl diformate. The preparation method comprises the following step of: with alpha-diethyl chlorooxalacetate and 2-ethyl acrolein as raw materials and ammonium acetate as a nitrogen source, preparing the 5-ethylpyridine-2,3-diethyl diformate in an ethanol medium. Compared with the prior art, the preparation method provided by the invention has the advantages that the output of three wastes is greatly reduced while the yield is not affected; partial solvent can be recycled; and only does single component of salt exist in wastewater, so that incineration disposal of the salt component is simple and complete and an incinerator cannot be blocked; and in the meantime, the quality of the 5-ethylpyridine-2,3-diethyl diformate is good; and therefore, the preparation method of 5-ethylpyridine-2,3-diethyl diformate is efficient, energy-saving and environmentally friendly.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to a preparation method of diethyl 5-ethylpyridine-2,3-dicarboxylate. Background technique [0002] Diethyl 5-ethylpyridine-2,3-dicarboxylate (referred to as cyclized product) is an intermediate widely used in the chemical industry such as medicine and pesticides, especially as an important intermediate of the pesticide imazethapyr. The structural formula is as follows: (I) as shown: [0003] [0004] During the synthesis of this intermediate, common ring-closing nitrogen sources include ammonium sulfamate, ammonia gas, and hydroxylamine sulfate. EP0452094A2 introduces the method of preparing cyclized compounds using hydroxylamine sulfate as nitrogen source; EP0274379A2, US4973695 and WO8908645A1 introduces the method of preparing cyclized compounds using ammonia as nitrogen source; The article "Clean Synthesis of Pesticide Intermediate 5-Ethylpyridine-2,3-dicarboxylate" on page 2...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/803C07D213/80
Inventor 程春生马晓华李子亮邓旭
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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