Acetic Anhydride → ethyl 2-(N-phenylformamido)acetate

HRID 37459

Reaction equation

HRID 37459 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:14])[CH2:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:3].[CH:15]([O-])=[O:16].[Na+].C(OC(=O)C)(=O)C>C(O)=O>[CH2:2]([O:4][C:5](=[O:14])[CH2:6][N:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:15]=[O:16])[CH3:3]

Participants

5

Reactant 3

HCID 7918Acetic Anhydride2×HCID 2723810Sodium FormateHCID 12241367Ethyl N-phenylglycinate hydrochloride

Product 1

HCID 14416604ethyl 2-(N-phenylformamido)acetate

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Phenylglycine ethyl ester hydrochloride (21.5 g; 0.1 mol) was dissolved in 200 ml of formic acid, whereto sodium formate (8.16 g; 1.2 eq.) was added, followed by adding dropwise acetic anhydride (20 ml; 2.1 eq.). After two hours' stirring, 10 ml of acetic anhydride was added dropwise, and the mixture was stirred at 50°-60° C. for 1.5 hours. After the solvent was distilled off, the residue was neutralized with an aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off to afford an oily product.

Workup

  1. stirringthe mixture was stirred at 50°-60° C. for 1.5 hours
  2. distillationAfter the solvent was distilled off
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customto afford an oily product

Sources & evidence

ORD record
ord-512e925bfd144f51b8b4b5a983f7a023
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Linked notes

Loading…