Dimethylformamide → HCID 178509930, Verbindung

HRID 505523

Reaktionsgleichung

Reaktionsgleichung von HRID 505523
Br[C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[O:5][C:6]1[C:14]2[N:13]=[N:12][NH:11][C:10]=2[CH:9]=[CH:8][C:7]=1[Cl:15].[CH3:20][N:21](C=O)C>CCOC(C)=O.[C-]#N.[Zn+2].[C-]#N>[Cl:19][C:17]1[CH:18]=[C:2]([CH:3]=[C:4]([O:5][C:6]2[C:14]3[N:13]=[N:12][NH:11][C:10]=3[CH:9]=[CH:8][C:7]=2[Cl:15])[CH:16]=1)[C:20]#[N:21]

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 1784778354-(3-bromo-5-chlorophenoxy)-5-chloro-1H-1,2,3-benzotriazole

Produkt 1

HCID 178509930HCID 178509930, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-(3-bromo-5-chlorophenoxy)-5-chloro-1H-1,2,3-benzotriazole (5.0 g, 14 mmol), tetrakis triphenylphosphine palladium (0) (4.83 g, 4.83 mmol) and zinc cyanide (1.96 g, 16.7 mmol) were suspended in dry DMF (50 mL) under N2 and placed in an oil bath at 90° C. After 2.5 hours, the reaction was allowed to cool to room temperature. The mixture was diluted with EtOAc (300 mL) and washed with water (4×100 mL), dried (MgSO4), filtered and concentrated with silica gel (20 g). This was purified by automated column chromatography on silica gel (120 g), eluting with 0-30% EtOAc/hexanes to deliver the title compound. LRMS (M+1)=304.8.

Aufarbeitung

  1. customplaced in an oil bath at 90° C
  2. washwashed with water (4×100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated with silica gel (20 g)
  6. customThis was purified by automated column chromatography on silica gel (120 g)
  7. washeluting with 0-30% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ca405af8e237421d88ecbd04e65b6f9d
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781454B2

Verknüpfte Notizen

Wird geladen…