Benzophenone imine → Ethyl 2-(diphenylmethyleneamino)acetate

HRID 1614700Notes

Reaction equation

HRID 1614700 reaction equation
[C:1](=[NH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.N[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>ClCCl>[C:2]1([C:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:14][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 136809Benzophenone imineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 319508Ethyl 2-(diphenylmethyleneamino)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzophenone imine (100 g, 0.54 mol), and 78.4 g, 0.56 mol) ethyl glycinate hydrochloride are combined in 2 L of dichloromethane and stirred overnight at room temperature. A precipitate (ammonium chloride) is filtered and the solution washed with water, dried over magnesium sulfate, and concentrated. The residual oil is dissolved in 200 mL of boiling diethyl ether, cooled to room temperature, and diluted with 600 mL of hexane. Some seed crystals from a previous experiment are added and the mixture cooled at +2° C. overnight. A white crystalline precipitate is collected and the mother liquor is concentrated to one-half of the volume, cooled overnight as above. This affords a second crop of product. The total yield is 133.0 g of the title compound; mp 52°-54° C.

Workup

  1. filtrationA precipitate (ammonium chloride) is filtered
  2. washthe solution washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. dissolutionThe residual oil is dissolved in 200 mL of boiling diethyl ether
  6. temperaturecooled to room temperature
  7. additiondiluted with 600 mL of hexane
  8. additionSome seed crystals from a previous experiment are added
  9. temperaturethe mixture cooled at +2° C. overnight
  10. customA white crystalline precipitate is collected
  11. concentrationthe mother liquor is concentrated to one-half of the volume
  12. temperaturecooled overnight as above
  13. customThis affords a second crop of product

Sources & evidence

ORD record
ord-e76cfbe07de84995bea3bbafda997f62
Source dataset
uspto-grants-1993_03
Patent number
US05198548

Reaction notes

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