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A process for preparation of dicyanocarboxylate derivatives

A technology of dicyanopropionate and cyano group, which is applied in the field of preparing dicyanocarboxylate derivatives, which can solve the problems of needing to be careful in the reaction, poor stability of formaldehyde cyanohydrin, decomposition, etc.

Active Publication Date: 2014-01-08
凯基·霍尔穆斯吉·加尔达
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, formaldehyde cyanohydrin is not stable and often undergoes violent decomposition when distillation is attempted
Again, the reaction requires care given the risk of forming dimeric by-products

Method used

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  • A process for preparation of dicyanocarboxylate derivatives
  • A process for preparation of dicyanocarboxylate derivatives
  • A process for preparation of dicyanocarboxylate derivatives

Examples

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example 1

[0097]0.6 liter of absolute ethanol and 51.46 g of sodium cyanide (1.05 mol) were charged into a glass reactor equipped with a central vertical stirrer and a vertical condenser, followed by stirring at 30°C for 4 hours to obtain a slurry. Alternatively, 125.00 g of ethyl 2-cyano-2-propenoate (1 mole) was stabilized by dissolving methanesulfonic acid (3% by weight) in 100 ml of ethanol to give a stabilized ethyl 2-cyano-2-propenoate solution. A stable solution of ethyl 2-cyano-2-propenoate was injected into the slurry at 20°C-25°C over 2 hours to obtain a reaction mixture. The reaction mixture was further stirred at 20°C-25°C for 4 hours to obtain a reaction mass containing ethyl 2,3-dicyanopropionate sodium salt. The reaction was monitored by unreacted sodium cyanide. Then, the reaction mixture containing ethyl 2,3-dicyanopropionate sodium salt was cooled to 10°C, and dry hydrogen chloride gas was bubbled to neutralize the sodium salt of ethyl 2,3-dicyanopropionate . Then,...

example 2

[0099] 0.6 liters of anhydrous methanol and 51.46 g of sodium cyanide (1.05 mol) were charged into a glass reactor equipped with a central vertical stirrer and a vertical condenser, followed by stirring at 30°C for 4 hours to obtain a slurry. Alternatively, 125.00 g of ethyl 2-cyano-2-propenoate (1 mole) was stabilized by dissolving methanesulfonic acid (3% by weight) in 100 mL of methanol to give a stabilized ethyl 2-cyano-2-propenoate solution. A stable solution of ethyl 2-cyano-2-propenoate was injected into the slurry at 20°C-25°C over 2 hours to obtain a reaction mixture. The reaction mixture was further stirred at 20°C-25°C for 4 hours to obtain a reaction mass containing ethyl 2,3-dicyanopropionate sodium salt. The reaction was monitored by unreacted sodium cyanide. Then, the reaction mixture containing ethyl 2,3-dicyanopropionate sodium salt was cooled to 10°C, and dry hydrogen chloride gas was bubbled to neutralize the sodium salt of ethyl 2,3-dicyanopropionate . ...

example 3

[0101] 0.6 liters of anhydrous isopropanol and 51.46 g of sodium cyanide (1.05 mol) were charged into a glass reactor equipped with a central vertical stirrer and a vertical condenser, followed by stirring at 30°C for 4 hours to obtain a slurry. Alternatively, 125.00 g of ethyl 2-cyano-2-propenoate (1 mole) was stabilized by dissolving methanesulfonic acid (3% by weight) in 100 ml of isopropanol to give ethyl 2-cyano-2-propenoate stable solution. A stable solution of ethyl 2-cyano-2-propenoate was injected into the slurry at 20°C-25°C over 2 hours to obtain a reaction mixture. The reaction mixture was further stirred at 20°C-25°C for 4 hours to obtain a reaction mass containing ethyl 2,3-dicyanopropionate sodium salt. The reaction was monitored by unreacted sodium cyanide. Then, the reaction mixture containing ethyl 2,3-dicyanopropionate sodium salt was cooled to 10°C, and dry hydrogen chloride gas was bubbled to neutralize the sodium salt of ethyl 2,3-dicyanopropionate . ...

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Abstract

The present disclosure provides a process for preparing 2, 3-dicyanopropionic acid ester of formula (I); said process comprising the following steps: i) treating an alkali metal cyanide dissolved in a solvent with a solution of 2-cyano-2-propenoic acid ester of formula (II) at a temperature ranging between 0 °C and 50 °C for a time period ranging between 2 hours and 15 hours followed by cooling below 20 °C to obtain a sodium salt of 2, 3-dicyanopropionic acid ester of formula (I); and (II) ii) neutralizing the sodium salt of 2, 3-dicyanopropionic acid ester using a neutralizing agent to obtain a 2, 3-dicyanopropionic acid ester of formula (I), (I)

Description

technical field [0001] The present invention relates to a process for the preparation of dicyanocarboxylate derivatives. Background technique [0002] 2,3-Dicyanopropionate derivatives are widely used in the synthesis of pyrazole derivatives. Pyrazole derivatives are used in the production of fine chemicals and agrochemicals with pesticidal or insecticidal properties as described in European Patent Publication Nos. 0295117, 0234119 and WO93 / 06089. [0003] Higson and Thorpe prepared ethyl 2,3-dicyanopropionate for the first time by reacting formaldehyde cyanohydrin with the sodium salt of ethyl cyanoacetate (Journal of Chemical Society Vol. 89, No. 1460 (1906) ). The reaction can be represented as follows: [0004] [0005] The process disclosed by Higson and Thorpe for the preparation of ethyl 2,3-dicyanopropionate suffers from significant drawbacks such as the instability of the formaldehyde cyanohydrin used as a reactant, its tendency to polymerize in the presence o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/10C07C255/19
CPCC07C253/10C07C255/19C07C253/30
Inventor 凯基·霍尔穆斯吉·加尔达
Owner 凯基·霍尔穆斯吉·加尔达
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