4-Nitroaniline → p-Nitrophenylurethane

HRID 724834

Reaktionsgleichung

Reaktionsgleichung von HRID 724834
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(CC)CC.Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(Cl)(Cl)Cl>[CH2:22]([O:21][C:19]([NH:8][C:7]1[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:20])[CH3:23]

Komponenten

5

Edukt 3

HCID 74754-NitroanilineHCID 8471TriethylamineHCID 10928Ethyl chloroformate

Produkt 1

HCID 230135p-Nitrophenylurethane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a cooled (0° C.) suspension of 4-nitroaniline (10 g, 0.072 mol) and Et3N (10 mL) in CHCl3 (120 mL), was added dropwise ethyl chloroformate (6.9 mL) and the mixture was stirred under an argon atmosphere at room temperature overnight. CHCl3 was added and the resulting solution was washed with 1N HCl. The layers were separated, the aqueous phase was washed with CHCl3 and the combined organic extracts were dried and concentrated. The residue was chromatographed on silica gel (hexane:EtOAc, 30%) to afford N-(ethoxycarbonyl)-4-nitroaniline (1.7 g).

Aufarbeitung

  1. temperatureTo a cooled
  2. washthe resulting solution was washed with 1N HCl
  3. customThe layers were separated
  4. washthe aqueous phase was washed with CHCl3
  5. customthe combined organic extracts were dried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel (hexane:EtOAc, 30%)

Quellen und Nachweise

ORD-Eintrag
ord-0aa353dec71e421e93b481f6562f52de
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05705504

Verknüpfte Notizen

Wird geladen…