Water → N-Phenylglycine ethyl ester

HRID 1728951Notes

Reaction equation

HRID 1728951 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([O:10][C:11](=[O:14])[CH2:12]Br)[CH3:9].C([O-])(=O)C.[Na+].O>C(O)C>[CH2:8]([O:10][C:11](=[O:14])[CH2:12][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 7748Ethyl bromoacetateHCID 517045Sodium Acetate

Product 1

HCID 75190N-Phenylglycine ethyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mechanically stirred mixture of aniline (71 g; 0.76 mol), ethylbromoacetate (127.5 g; 0.76 mol), and anhydrous sodium acetate (62.6 g; 0.76 mol) in absolute ethanol (10 mL) was heated at reflux for 6 hours. The mixture was cooled, water was added to precipitate the product, and the solid was filtered and dried. The crude product was crystallized from ethanol-water to give N-phenylglycine ethyl ester (107 g; 79%) having amp 48°-49° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. temperatureThe mixture was cooled
  4. customto precipitate the product
  5. filtrationthe solid was filtered
  6. customdried
  7. customThe crude product was crystallized from ethanol-water

Sources & evidence

ORD record
ord-5c2f9751cb934d41bdb01b9d7faf92ac
Source dataset
uspto-grants-1994_07
Patent number
US05329012

Reaction notes

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