Lithium Hydroxide → 2-(5-Fluoro-2-nitro-phenylamino)-5-isopropyl-benzonitrile

HRID 131330

Reaktionsgleichung

Reaktionsgleichung von HRID 131330
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:6][C:3]=1[C:4]#[N:5].F[C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22].[OH-].[Li+].C(OCC)(=O)C>CS(C)=O>[F:20][C:18]1[CH:17]=[CH:16][C:15]([N+:21]([O-:23])=[O:22])=[C:14]([NH:1][C:2]2[CH:9]=[CH:8][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:6][C:3]=2[C:4]#[N:5])[CH:19]=1

Komponenten

6

Edukt 4

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 679672,4-DifluoronitrobenzeneHCID 210934632-Amino-5-isopropylbenzonitrile

Produkt 1

HCID 586259572-(5-Fluoro-2-nitro-phenylamino)-5-isopropyl-benzonitrileAusbeute 16,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Heat a solution of 2-amino-5-isopropyl-benzonitrile (1.21 g, 7.55 mmol) with 2,4-difluoro-1-nitro-benzene (1.20 g, 7.55 mmol) and lithium hydroxide (0.54 g, 22.66 mmol) in DMSO (15 ml) to 70° C. for 18 hours. Cool the reaction to ambient temperature and then pour into approximately 200 ml of ice water and stir for one hour. The title compound precipitates and is colleted by filtration. Purify the solid via flash chromatography eluting with a 95% hexanes: 5% ethyl acetate mobile phase to obtain 0.372 g (1.24 mmol, 16% yield) of the title compound as an orange amorphous solid: Mass Spectrum (m/e): 298 (M−1).

Aufarbeitung

  1. temperatureCool
  2. customthe reaction to ambient temperature
  3. customThe title compound precipitates
  4. filtrationis colleted by filtration
  5. customPurify the solid via flash chromatography
  6. washeluting with a 95% hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c4491ebbc188498abc9e2e87309ba20e
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384934B2

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