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

HRID 1392758Notes

Reaction equation

HRID 1392758 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 esterYield 85.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

4-Chloroaniline (2.0 g) was dissolved in acetonitrile (20 ml), and ethyl bromoacetate (2.1 g) and potassium carbonate (2.2 g) were added to stir the mixture at 60° C. for 2 days. The reaction mixture was filtered through Celite pad, and the filtrate was concentrated under reduced pressure. The resultant residue was purified by column chromatography on silica gel (hexane:chloroform=2:1) to obtain the title compound (2.3 g).

Workup

  1. filtrationThe reaction mixture was filtered through Celite pad
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resultant residue was purified by column chromatography on silica gel (hexane:chloroform=2:1)

Sources & evidence

ORD record
ord-ddfb4b074a4041119d5d2fc3840b3ecd
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

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