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O-Xylene → 1-(4-Bromophenyl)-2-phenyl-1H-benzimidazole

HRID 1172774
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1172774
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16](=O)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.C1(C)C(C)=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>O.ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:15]=[C:16]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 7237O-XyleneHCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 23160217N-[2-(4-bromophenylamino)phenyl]benzamide

Produkt 1

HCID 230940711-(4-Bromophenyl)-2-phenyl-1H-benzimidazoleAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2.1 g (5.7 mmol) of N-[2-(4-bromophenylamino)phenyl]benzamide were suspended into 30 mL of xylene, 0.6 g (2.9 mmol) of p-toluenesulfonic acid monohydrate was added, and the whole was refluxed under heating for 3 hours. After the resultant had been stood to cool, the reaction solution was added with ethyl acetate, dichloromethane, and water for filtering insoluble matter out. An organic layer was extracted from a mother liquor, washed with water and a saturated sodium chloride solution, and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by means of silica gel column chromatography to obtain 1.0 g of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole (52% yield).

Aufarbeitung

  1. additionwas added
  2. temperaturethe whole was refluxed
  3. temperatureunder heating for 3 hours
  4. temperatureto cool
  5. filtrationfor filtering insoluble matter out
  6. extractionAn organic layer was extracted from a mother liquor
  7. washwashed with water
  8. dry with materiala saturated sodium chloride solution, and dried with anhydrous sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by means of silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-84a522a111994de28722d0611d40d82f
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07833632B2

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