2,4-Difluoronitrobenzene → 2-(5-Fluoro-2-nitro-phenylamino)-thiophene-3-carbonitrile

HRID 131380

Reaktionsgleichung

Reaktionsgleichung von HRID 131380
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH2:12][C:13]1[S:14][CH:15]=[CH:16][C:17]=1[C:18]#[N:19].O.[OH-].[Li+]>CS(C)=O>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([NH:12][C:13]2[S:14][CH:15]=[CH:16][C:17]=2[C:18]#[N:19])[CH:7]=1

Komponenten

5

Edukt 3

HCID 679672,4-DifluoronitrobenzeneHCID 168937Lithium hydroxide, monohydrateHCID 7366072-Aminothiophene-3-carbonitrile

Produkt 1

HCID 692118502-(5-Fluoro-2-nitro-phenylamino)-thiophene-3-carbonitrileAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Combine 2,4-difluoro-1-nitro-benzene (5.24 g, 32.94 mmol), 2-aminothiophene-3-carbonitrile (4.09 g, 32.94 mmol), and DMSO (30.0 ml). Add lithium hydroxide monohydrate (2.76 g, 65.88 mmol) all at once and then stir the mixture at 55° for 22 hours. Cool the mixture to ambient temperature and then pour it onto ice chips. Extract with ethyl acetate and then wash (brine), dry (sodium sulfate), and evaporate the organic to residue. Purify the residue on silica gel using hexanes/dichloromethane (35:65) to give 3.89 g (45%) of the title compound as a red solid: mass spectrum (ion spray): m/z=262.0 (M−1).

Aufarbeitung

  1. additionpour it onto ice chips
  2. extractionExtract with ethyl acetate
  3. washwash (brine)
  4. dry with materialdry (sodium sulfate)
  5. customevaporate the organic to residue
  6. customPurify the residue on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-2c4b8a4f82994450bcaa96a83066b968
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384934B2

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