Glycine ethyl ester → HCID 73680293, compound

HRID 1980962Notes

Reaction equation

HRID 1980962 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7](=[CH:10][N:11]([CH3:13])C)[CH:8]=[O:9])=[CH:4][CH:3]=1.NC[C:18]([O:20][CH2:21][CH3:22])=[O:19].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7](=[CH:10][NH:11][CH2:13][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:8]=[O:9])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 12176Glycine ethyl esterHCID 14798Sodium HydroxideHCID 54237126HCID 54237126, compound

Product 1

HCID 73680293HCID 73680293, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(4-Chlorophenoxy)-3-dimethylaminoacrylaldehyde (11.3 g., 50 mmoles) was dissolved in 200 ml. of ethanol, mixed with a solution of ethyl glycinate (14 g., 100 mmoles) in 90 ml. of 1N sodium hydroxide and refluxed for 15 hours. Ethanol was evaporated in vacuo, the aqueous residue diluted with 150 ml. of water and product extracted into 200 ml. of ethyl acetate. The ethyl acetate was back-washed with water and concentrated to an oil. Trituration of the oil with 100 ml. of ether gave crystalline 2-(4-chlorophenoxy)-3-carbethoxymethylaminoacrylaldehyde in two crops (7.3 g., Rf 0.55 on silica gel thin layer chromatography with ethyl acetate-1/hexane-1/5% acetic acid as eluant).

Workup

  1. customEthanol was evaporated in vacuo
  2. additionthe aqueous residue diluted with 150 ml
  3. extractionof water and product extracted into 200 ml
  4. washThe ethyl acetate was back-washed with water
  5. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-91b2ed42cf2d40d9aeb385cb0763f9c2
Source dataset
uspto-grants-1985_04
Patent number
US04511575

Reaction notes

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