N-Phenylglycine ethyl ester → ethyl 2-(N-phenylformamido)acetate

HRID 1728952Notes

Reaction equation

HRID 1728952 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].[CH:14](OC(=O)C)=[O:15]>O>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][N:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH:14]=[O:15])[CH3:2]

Participants

4

Reactant 2

HCID 75190N-Phenylglycine ethyl esterHCID 75269Acetic-formic anhydride

Product 1

HCID 14416604ethyl 2-(N-phenylformamido)acetateYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-Phenylglycine ethyl ester (100 g; 0-56 mol) was added in small portions to acetic formic anhydride (100 g; 1.14 mol) with vigorous stirring. The mixture was allowed to stir overnight, then it was poured into water, and extracted with ether. The ether solution was washed with sodium bicarbonate solution and then with water. The ether was evaporated in vacuo to give an oil which was distilled to give N-phenyl-N-formylglycine ethyl ester (81 g; 70%) having a bp 115°-117° C.

Workup

  1. extractionextracted with ether
  2. washThe ether solution was washed with sodium bicarbonate solution
  3. customThe ether was evaporated in vacuo
  4. customto give an oil which
  5. distillationwas distilled

Sources & evidence

ORD record
ord-ab70f6dde5414ecabec30cbd5dd807d6
Source dataset
uspto-grants-1994_07
Patent number
US05329012

Reaction notes

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