Ethyl cyanoacetate → HCID 19979312, compound

HRID 1461747Notes

Reaction equation

HRID 1461747 reaction equation
[Na].[C:2]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])#[N:3].[CH3:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1Cl)=[O:12]>C(O)C>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:11](=[O:12])[CH2:10][CH:4]([C:2]#[N:3])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 27365072'-Chloro-4'-fluoroacetophenoneHCID 5360545Sodium

Product 1

HCID 19979312HCID 19979312, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 86.7 g of sodium in 4,500 ml of anhydrous ethanol is added at 15° C. to a solution of 528 g of ethyl cyanoacetate in 500 ml of anhydrous ethanol. After one hour, the mixture is cooled to 0° C. and a solution of 620 g of 2-chloro-4-fluoroacetophenone in one liter of ethanol is added to the solution obtained. The reaction mixture is left for 12 hours at room temperature, then hydrolyzed with 200 ml of water and concentrated. The residue is taken up in one liter of water and this aqueous phase is neutralized to pH 7 and extracted with dichloromethane, followed by concentration.

Workup

  1. customobtained
  2. waitThe reaction mixture is left for 12 hours at room temperature
  3. concentrationhydrolyzed with 200 ml of water and concentrated
  4. extractionextracted with dichloromethane
  5. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-a87901cb6a4448e090d4231e2a2b5b24
Source dataset
uspto-grants-1991_12
Patent number
US05077288

Reaction notes

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