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

HRID 723668

Reaktionsgleichung

Reaktionsgleichung von HRID 723668
[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-814226664a614ae5ace7aa0e65cd60e6
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141578B2

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