Stannous Chloride → 7-Fluoro-2-trifluoromethyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride

HRID 131329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 131329
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:21]([O-])=O)=[C:6]([NH:8][C:9]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:10]=2[C:11]#[N:12])[CH:7]=1.[Sn](Cl)[Cl:25]>C(O)C.Cl>[ClH:25].[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:21]=[C:11]([NH2:12])[C:10]3[CH:13]=[C:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=[CH:16][C:9]=3[NH:8][C:6]=2[CH:7]=1

Komponenten

5

Edukt 2

HCID 24479Stannous ChlorideHCID 586259682-(5-Fluoro-2-nitro-phenylamino)-5-trifluoromethyl-benzonitrile

Produkt 1

HCID 692107787-Fluoro-2-trifluoromethyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochlorideAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel2×HCID 702EthanolLösungsmittel

Versuchsvorschrift

Heat a solution of 2-(5-fluoro-2-nitro-phenylamino)-5-trifluoromethyl-benzonitrile (1.62 g, 4.98 mmol) in ethanol (24 ml) to 60° C. Add to this a solution of tin (II) chloride (2.83 g, 14.94 mmol) in 5.0 N hydrochloric acid (24 ml). Heat the resulting mixture to reflux for 20 hours. Cool the reaction to room temperature, add 30 ml of 5.0 N hydrochloric acid and place the mixture in a freezer for 16 hours. The product precipitates from the solution and is collected by filtration. Wash solid with 5.0 N hydrochloric acid to obtain 1.44 g of the title compound (4.34 mmol, 87% yield) as a yellow amorphous solid: Mass Spectrum (m/e): 295(M+1).

Aufarbeitung

  1. temperatureHeat the resulting mixture
  2. temperatureto reflux for 20 hours
  3. temperatureCool
  4. customthe reaction to room temperature
  5. customThe product precipitates from the solution
  6. filtrationis collected by filtration
  7. washWash solid with 5.0 N hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-73cdee70a305492496ff948ff45cc59b
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384934B2

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