Benzophenone imine → Ethyl 2-(diphenylmethyleneamino)acetate

HRID 2294950Notes

Reaction equation

HRID 2294950 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].[C:9](=N)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>ClCCl.O>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][N:7]=[C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:3]

Participants

5

Reactant 2

HCID 136809Benzophenone imineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 319508Ethyl 2-(diphenylmethyleneamino)acetateYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of glycine ethylester, monohydrochloride (13.96 g, 100 mmol) and benzophenone imine (18.1 g, 100 mmol) in distilled dichloromethane (600 mL) was stirred at room temperature (RT) for 24 hours (h.). The mixture was diluted with water (250 mL) and the dichloromethane extract was separated, dried (MgSO4), filtered and concentrated under reduced pressure and in vacuo to obtain ethyl-N-(diphenylmethylene)-glycinate as a white solid (25.3 g, 95%). Ref.: M. J. O'Donnell, R. L. Polt J. Org, Chem. 47, 2663, 1982.

Workup

  1. extractionthe dichloromethane extract
  2. customwas separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure and in vacuo

Sources & evidence

ORD record
ord-292967d20b4e41b1bb5bb140e3bc1a69
Source dataset
uspto-grants-1997_11
Patent number
US05691356

Reaction notes

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