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

HRID 37459Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 37459
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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 14416604ethyl 2-(N-phenylformamido)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-512e925bfd144f51b8b4b5a983f7a023
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420275

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