Glycine → N-(Iminophenylmethyl)glycine

HRID 1939647Notes

Reaction equation

HRID 1939647 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].[C:8](=[NH:18])(OCC)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O.CO>[C:8]([NH:1][CH2:2][C:3]([OH:5])=[O:4])(=[NH:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 750GlycineHCID 14798Sodium HydroxideHCID 79250Ethyl benzimidate

Product 1

HCID 178512216N-(Iminophenylmethyl)glycine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A white suspension of glycine (3.81 g, 50 mmol) in water (0.9 g) and methanol (16 ml) was stirred at room temperature, adjusted to pH 9.6 by the addition of sodium hydroxide solution and admixed with ethyl benzimidate (7.69 g, 50 mmol). The mixture was heated for 1 hour at 50° C. and allowed to cool at room temperature. The solid was filtered off, washed with toluene and dried at room temperature/30 mbar. The yield of the title compound was 6.81 g (approximately 95 percent pure by H-NMR), 74 percent based on glycine. Other data concerning the title compound was:

Workup

  1. temperatureThe mixture was heated for 1 hour at 50° C.
  2. temperatureto cool at room temperature
  3. filtrationThe solid was filtered off
  4. washwashed with toluene
  5. customdried at room temperature/30 mbar

Sources & evidence

ORD record
ord-0605053b24f845479ecddd9b50741846
Source dataset
uspto-grants-1997_12
Patent number
US05696272

Reaction notes

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