Methyl iodide → (Methyl-phenyl-amino)-acetic acid ethyl ester

HRID 2184086Notes

Reaction equation

HRID 2184086 reaction equation
[C:1]1([NH:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[CH3:15]>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:15][N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 75190N-Phenylglycine ethyl ester

Product 1

HCID 265936(Methyl-phenyl-amino)-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl N-Phenylglycinate (2 g, 11.1 mmol) was dissolved in toluene (4.5 mL) and iodomethane (0.35 mL, 5.6 mmol) added. After warming at 70° C. over 4 hours, the reaction mixture was cooled to ambient temperature and diluted with EtOAc. The organic layer was washed several times with brine, dried (Na2SO4), filtered, and concentrated. Purification by flash chromatography (10:1 hexanes/EtOAc) afforded a quantitative yield of the title compound as a light yellow oil. MS (ES+) m/z 194 (MH+).

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. washThe organic layer was washed several times with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (10:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-4e8cd66d223a459cad3b478200d62ef3
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Reaction notes

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