Triethylamine → [[(3-Nitrophenyl)amino]carbonyl]aminoacetic acid methyl ester

HRID 1785309

Reaktionsgleichung

Reaktionsgleichung von HRID 1785309
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]=[C:11]=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.[CH3:14][O:15][C:16](=[O:19])[CH2:17][NH2:18].C(N(CC)CC)C>ClCCl>[CH3:14][O:15][C:16](=[O:19])[CH2:17][NH:18][C:11]([NH:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:12]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 768353-Nitrophenyl isocyanateHCID 122755Glycine methyl ester hydrochloride

Produkt 1

HCID 10934009[[(3-Nitrophenyl)amino]carbonyl]aminoacetic acid methyl esterAusbeute 97,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 3-nitrophenyl isocyanate (10 g, 61 mmol) and glycine methyl ester hydrochloride (8.4 g, 67 mmol, 1.1 equiv.) in dichloromethane (250 mL) was added triethylamine (10 mL, 72 mmol, 1.2 equiv.) at 0° C. The resulting solution was stirred at room temperature overnight. The resulting dark brown solution was concentrated and triturated in water to give a light yellow suspension. The suspension was filtered and the filter cake was washed with water and air-dried to give [[[(3-nitrophenyl)amino]carbonyl]aminoacetic acid methyl ester (15 g) in quantitative yield.

Aufarbeitung

  1. concentrationThe resulting dark brown solution was concentrated
  2. customtriturated in water
  3. customto give a light yellow suspension
  4. filtrationThe suspension was filtered
  5. washthe filter cake was washed with water
  6. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-7cbb34cd19a849b0a82cafe0f9ba6d7b
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504410B2

Verknüpfte Notizen

Wird geladen…