Ethyl bromoacetate → Glycine, N-(4-chlorophenyl)-, ethyl ester

HRID 1404190Notes

Reaction equation

HRID 1404190 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Br[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 78124-ChloroanilineHCID 11430Potassium Carbonate

Product 1

HCID 302644Glycine, N-(4-chlorophenyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-chloroaniline (12.8 g, 100.3 mmol), ethyl bromoacetate (12.2 mL, 110.4 mmol). and potassium carbonate (13.9 g, 100.3 mmol) in acetonitrile (330 mL) was heated overnight at 80° C. The resulting mixture was cooled to room temperature and filtered. The filtrate was concentrated and triturated DCM and the resulting solid was filtered to yield ethyl 2-((4-chlorophenyl)amino)acetate.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customtriturated DCM
  4. filtrationthe resulting solid was filtered

Sources & evidence

ORD record
ord-4398a951344b4c399587f817dc1803f9
Source dataset
uspto-grants-2014_12
Patent number
US08912227B1

Reaction notes

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