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Synthetic method of 3-ethoxyacrylonitrile and 3,3-diethoxypropionitrile mixture

A technology of ethoxyacrylonitrile and diethoxypropionitrile is applied in the field of synthesis of a mixture of 3-ethoxyacrylonitrile and 3,3-diethoxypropionitrile, and can solve the problem of high reaction pressure and high yield. It is not high, the reaction balance is different, etc., to achieve the effects of mild reaction conditions, low cost of raw materials, and simple operation

Active Publication Date: 2022-01-21
NANJING OCEAN PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The disadvantages of this process are: (1) The reaction pressure is high. We know that in industrial production, the pressure condition is too high, which will not only significantly increase the production cost, but also have strict requirements on production conditions and production equipment, and at the same time pose a safety hazard. (2) The reaction of the raw material is not complete, and the reaction equilibrium is different for different reactions. In a specific reaction, when the reaction equilibrium is reached, the raw material will not further react to form the product, so there will be a certain amount of raw material in the product Among them, thereby not only reducing the yield of the overall reaction, but also affecting the subsequent purification process, increasing the difficulty of product purification and reducing the purity of the product
[0010] The second method is chemical world, 2012,53 (7): 429-431 literature report, disclosed in this open literature with 1,1,3,3-tetraethoxypropane and hydroxylamine hydrochloride as the starting point The starting material is first synthesized to obtain isoxazole, and then isoxazole and diethyl sulfate are used to prepare a mixture of 3-ethoxyacrylonitrile and 3,3-diethoxypropionitrile under alkaline conditions. This method can To overcome the low yield of the first method, its total yield can reach 78%, but the raw material 1,1,3,3-tetraethoxypropane used in this method is expensive and not suitable for Industrial production

Method used

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  • Synthetic method of 3-ethoxyacrylonitrile and 3,3-diethoxypropionitrile mixture
  • Synthetic method of 3-ethoxyacrylonitrile and 3,3-diethoxypropionitrile mixture
  • Synthetic method of 3-ethoxyacrylonitrile and 3,3-diethoxypropionitrile mixture

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Embodiment 1

[0041] 24.50 grams of sodium methoxide and 300 grams of acetonitrile were put into a 600ml autoclave, the autoclave was sealed, ice-salt bath was used for 20 minutes, and 33.6 grams of ethyl formate was inhaled. Nitrogen gas 1.50MPa was introduced. Stir and heat up to 110°C, keep the reaction for 15 hours, then cool down to room temperature. Compound II was prepared as a white paste, diluted with 200 g of acetonitrile (CAN), added into a 1 L three-neck flask, and stirred mechanically. Then add 1.50 grams of tetrabutylammonium bromide and 63 grams of diethyl sulfate. Add 6.5 g of triethylamine, raise the temperature to 40° C., stir at this temperature for 10 hours, and cool down to room temperature. After filtration, the solid was slurried with 100 g of acetonitrile, filtered to dryness, and the mother liquor was spin-dried at 50° C., and distilled to obtain a mixture I with a yield of 98.6% and a purity of 96.3%.

Embodiment 2

[0043] 24.50 grams of sodium methoxide and 370 grams of acetonitrile were put into a 600ml autoclave, the autoclave was sealed, ice-salt bath was used for 20 minutes, and 33.6 grams of ethyl formate was inhaled. Nitrogen gas 1.50MPa was introduced. Stir and heat up to 110°C, keep the reaction for 15 hours, then cool down to room temperature. Compound II was prepared as a white paste, diluted with 200 g of acetonitrile (ACN), added to a 1 L three-neck flask, and mechanically stirred. Then add 1.50 grams of tetrabutylammonium bromide and 63 grams of diethyl sulfate. Add 6.5 g of triethylamine, raise the temperature to 50° C., stir at this temperature for 28 hours, and cool down to room temperature. After filtration, the solid was slurried with 100 g of acetonitrile, filtered to dryness, and the mother liquor was spin-dried at 50° C., and distilled to obtain a mixture I with a yield of 96.5% and a purity of 95%.

Embodiment 3

[0045] Put 24.50 grams of sodium methoxide and 300 grams of acetonitrile into a 600ml autoclave, seal the autoclave, take an ice-salt bath for 20 minutes, and inhale 100 grams of ethyl formate. Introduce nitrogen gas 1.0MPa. Stir and heat up to 110°C, keep the reaction for 15 hours, then cool down to room temperature. Compound II was prepared as a white paste, diluted with 200 g of acetonitrile (ACN), added to a 1 L three-neck flask, and mechanically stirred. Add 1.50 grams of pentadecone and 77 grams of diethyl sulfate. Add 6.5 g of triethylamine, raise the temperature to 60° C., stir at this temperature overnight (more than 12 hours), and cool down to room temperature. After filtration, the solid was slurried with 100 g of acetonitrile, filtered to dryness, and the mother liquor was spin-dried at 50° C., and distilled to obtain a mixture I with a yield of 96.1% and a purity of 94.8%.

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Abstract

The invention belongs to the field of medicinal chemistry, in particular to the field of organic synthesis in medicinal chemistry, and more specifically relates to a synthesis method of a mixture of 3-ethoxyacrylonitrile and 3,3-diethoxypropionitrile. The method uses acetonitrile and formate under the action of alcohol alkali metal salts to obtain the intermediate compound II, and then the compound II reacts with diethyl sulfate under the action of a phase transfer catalyst to obtain the target compound compound I, namely Mixture of 3‑ethoxyacrylonitrile and 3,3‑diethoxypropionitrile. The synthesis method of the mixture of 3-ethoxyacrylonitrile and 3,3-diethoxypropionitrile disclosed by the present invention has the advantages of low raw material cost, relatively mild reaction conditions, simple operation, high yield, etc., and is suitable for Methods of industrial production and application.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to the field of organic synthesis in medicinal chemistry, and more specifically relates to a synthesis method of a mixture of 3-ethoxyacrylonitrile and 3,3-diethoxypropionitrile. Background technique [0002] 3-ethoxyacrylonitrile and 3,3-diethoxypropionitrile are important pharmaceutical intermediates for the synthesis of cytosine, cytosine derivatives and vitamin Bl precursors. In recent years, with the expiry of the patent protection period of a batch of anti-HIV, hepatitis B virus and other best-selling drugs, the amount of cytosine intermediates, as their necessary intermediates, will increase with the substantial increase in the production capacity of corresponding drugs. [0003] Therefore, the synthesis technology of 3-ethoxyacrylonitrile and 3,3-diethoxypropionitrile has become a research hotspot both at home and abroad. [0004] At present, the common methods for synthe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C253/30C07C255/13C07C255/15
Inventor 陈本顺江涛潘声成毛玲妙
Owner NANJING OCEAN PHARMA TECH