Sodium Carbonate → 1h-Benzo[d]imidazole,5-(4-chlorophenyl)-1,2-diphenyl-

HRID 1172763Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1172763
Br[C:2]1[CH:22]=[CH:21][C:5]2[N:6]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[CH:22]=[CH:21][C:5]3[N:6]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:7]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)=[N:8][C:4]=3[CH:3]=2)=[CH:26][CH:25]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 230940595-bromo-1,2-diphenyl-1H-benzo[d]imidazole

Produkt 1

HCID 231602311h-Benzo[d]imidazole,5-(4-chlorophenyl)-1,2-diphenyl-Ausbeute 83,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

2.5 g (7.2 mmol) of 5-bromo-1,2-diphenyl-1H-benzimidazole, 1.2 g (7.9 mmol) of 4-chlorophenylboronic acid, and 0.17 g (0.14 mmol) of tetrakis(triphenylphosphine)palladium were dissolved into 20 mL of 1,2-dimethoxyethane. Then, 10 mL of a 2 M aqueous solution of sodium carbonate were added, and the whole was refluxed under heating for 8 hours in an argon atmosphere. After the resultant had been stood to cool, an aqueous layer was removed and an organic layer was dried with magnesium sulfate. After the solvent had been distilled off under reduced pressure, the resultant solid was purified by means of silica gel column chromatography to obtain 2.3 g of 5-(4-chlorophenyl)-1,2-diphenyl-1H-benzimidazole (83% yield).

Aufarbeitung

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 8 hours in an argon atmosphere
  3. temperatureto cool
  4. customan aqueous layer was removed
  5. dry with materialan organic layer was dried with magnesium sulfate
  6. distillationAfter the solvent had been distilled off under reduced pressure
  7. customthe resultant solid was purified by means of silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b8aa58c6fa224b40adb25fde13816e39
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07833632B2

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