Sodium hydride → HCID 58626050, Verbindung

HRID 131387

Reaktionsgleichung

Reaktionsgleichung von HRID 131387
F[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[NH2:13][C:14]1[S:15][CH:16]=[CH:17][C:18]=1[C:19]#[N:20].[H-].[Na+]>C1COCC1>[F:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([NH:13][C:14]2[S:15][CH:16]=[CH:17][C:18]=2[C:19]#[N:20])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydride2×HCID 750121,2,4-Trifluoro-5-nitrobenzeneHCID 7366072-Aminothiophene-3-carbonitrile

Produkt 1

HCID 58626050HCID 58626050, VerbindungAusbeute 59,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Combine 2,4,5-trifluoro-nitrobenzene (5.00 g, 24.24 mmol), 2-aminothiophene-3-carbonitrile (3.51 g, 28.24 mmol), and anhydrous THF (30.0 ml). Cool the mixture to 10° and then slowly add NaH (2.26 g, 56.47 mmol, 60% dispersion in mineral oil) while keeping the temperature less than 10°. Warm the mixture to ambient temperature after NaH addition is complete. Stir the mixture at ambient temperature for 24 hours and then pour it onto ice chips. Extract the aqueous with ethyl acetate and then wash (brine), dry (sodium sulfate), and reduce the organic to residue. Purify the residue on silica gel using hexanes/dichloromethane (35:65) to give 4.06 g (51%) of the title compound as a red solid: mass spectrum (ion spray): m/z=280.0 (M−1).

Aufarbeitung

  1. temperatureCool the mixture to 10°
  2. customthe temperature less than 10°
  3. additionpour it onto ice chips
  4. extractionExtract the aqueous with ethyl acetate
  5. washwash (brine)
  6. dry with materialdry (sodium sulfate)
  7. customPurify the residue on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f77bc77ed57b4ba6a85f9220e50896c2
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384934B2

Verknüpfte Notizen

Wird geladen…