Imidazole → HCID 59333299, Verbindung

HRID 1893476Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1893476
[Br:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].[NH:16]1[CH:20]=[CH:19][N:18]=[CH:17]1.C(N(CC)C(C)C)(C)C>C(#N)C>[Br:1][C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[CH:7]=1

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 81531DiisopropylethylamineHCID 594197851-Bromo-5-fluoro-4-nitro-2-(trifluoromethyl)benzene

Produkt 1

HCID 59333299HCID 59333299, VerbindungAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 1-bromo-5-fluoro-4-nitro-2-(trifluoromethyl)benzene (16.0 g, 0.0556 mol), imidazole (4.0 g, 0.0588 mol) and N,N-diisopropylethylamine (10.1 mL, 0.0582 mol) in acetonitrile (160 mL) is stirred under nitrogen for 1.5 hour at 80° C. After concentration of the reaction mixture, the residue is partitioned between water and ethyl acetate. The aqueous phase is extracted with ethyl acetate, the combined organic phases are washed in turn with a saturated solution of ammonium chloride, brine and dried over sodium sulfate. Concentration and purification by cake filtration over silica gel, eluting with a mixture of ethyl acetate and cyclohexane from 2/8 to 1/1 affords the title compound as a yellow solid (16.1 g, 86.2%)

Aufarbeitung

  1. customAfter concentration of the reaction mixture, the residue is partitioned between water and ethyl acetate
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. washthe combined organic phases are washed in turn with a saturated solution of ammonium chloride, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration and purification
  6. filtrationby cake filtration over silica gel
  7. washeluting with a mixture of ethyl acetate and cyclohexane from 2/8 to 1/1

Quellen und Nachweise

ORD-Eintrag
ord-4242963cda404db48465ed51562c1e37
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513250B2

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