Phosphorus pentachloride → 1-(2,4-diisopropyldibenzo[b,d]thiophen-3-yl)-2-phenyl-4,5-dihydro-1H-imidazole

HRID 1750928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1750928
Cl[CH2:2][CH2:3][NH:4][C:5](=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[CH:19]([C:22]1[C:34]([NH2:35])=[C:33]([CH:36]([CH3:38])[CH3:37])[C:25]2[S:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:24]=2[CH:23]=1)([CH3:21])[CH3:20]>C1(C)C=CC=C(C)C=1>[CH:19]([C:22]1[C:34]([N:35]2[CH2:2][CH2:3][N:4]=[C:5]2[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[C:33]([CH:36]([CH3:38])[CH3:37])[C:25]2[S:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:24]=2[CH:23]=1)([CH3:21])[CH3:20]

Komponenten

5

Edukt 3

HCID 24819Phosphorus pentachlorideHCID 101439N-(2-chloroethyl)benzamideHCID 584010202,4-Diisopropyldibenzo[b,d]thiophen-3-amine

Produkt 1

HCID 584008491-(2,4-diisopropyldibenzo[b,d]thiophen-3-yl)-2-phenyl-4,5-dihydro-1H-imidazoleAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7929M-XyleneLösungsmittel

Versuchsvorschrift

N-(2-chloroethyl)benzamide (4.3 g, 23.42 mmol), was dissolved in 50 mL anhydrous m-xylene under nitrogen. Phosphorus pentachloride (7.31 g, 35.1 mmol) was then carefully added and the mixture heated to reflux under nitrogen for 2 h. The solution was allowed to cooled to room temperature and 2,4-diisopropyldibenzo[b,d]thiophen-3-amine (7.30 g, 25.8 mmol) was added. The reaction mixture was heated to reflux for 20 h. After cooling, the precipitate was filtered and the solid imidazoline product was collected and washed with toluene followed by hexanes. The resultant crude product was dissolved in methylene chloride and washed twice with 50% NaOH. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to afford title product (4.8 g, 50%).

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureto reflux under nitrogen for 2 h
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 20 h
  5. temperatureAfter cooling
  6. filtrationthe precipitate was filtered
  7. customthe solid imidazoline product was collected
  8. washwashed with toluene
  9. dissolutionThe resultant crude product was dissolved in methylene chloride
  10. washwashed twice with 50% NaOH
  11. dry with materialThe organic layer was dried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0b3516eebaa94049bc25400f5eed41e1
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156870B2

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