NBD-Cl → 7-Chloro-2,1,3-benzoxadiazol-4-amine

HRID 966901

Reaktionsgleichung

Reaktionsgleichung von HRID 966901
[Cl:1][C:2]1[C:7]2=[N:8][O:9][N:10]=[C:6]2[C:5]([N+:11]([O-])=O)=[CH:4][CH:3]=1>CC(O)=O.CCOC(C)=O.O.[Fe]>[NH2:11][C:5]1[C:6]2[C:7](=[N:8][O:9][N:10]=2)[C:2]([Cl:1])=[CH:3][CH:4]=1

Komponenten

6

Edukt 1

HCID 25043NBD-Cl

Produkt 1

HCID 218751677-Chloro-2,1,3-benzoxadiazol-4-amineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 1.0 g (5.02 mmol) of 4-chloro-7-nitrobenzofurazan in 20 mL AcOH, 10 mL EtOAc and 2 mL H2O was heated at 50° C. and treated with iron powder (1.4 g, 251 mmol). The mixture was heated at 80° C. for 30 min and then allowed to cool to rt. The mixture was filtered through Celite eluting with EtOAc. The filtrate was washed with sat. aq. NaHCO3, dried over MgSO4, and concentrated under reduced pressure to give compound 258A (0.80 g, 94%) as a red solid.

Aufarbeitung

  1. temperatureto cool to rt
  2. filtrationThe mixture was filtered through Celite
  3. washeluting with EtOAc
  4. washThe filtrate was washed with sat. aq. NaHCO3
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-26a2fc2eb88d4fbca4c90a503bb6f641
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06953679B2

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