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

HRID 1750900Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1750900
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[O: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[O: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 584009912,4-Diisopropyldibenzo[b,d]furan-3-amine

Produkt 1

HCID 584008541-(2,4-diisopropyldibenzo[b,d]furan-3-yl)-2-phenyl-4,5-dihydro-1H-imidazoleAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7929M-XyleneLösungsmittel

Versuchsvorschrift

N-(2-chloroethyl)benzamide (4.12 g, 22.44 mmol) and phosphorous pentachloride (7.01 g, 33.7 mmol) were refluxed in m-xylene under nitrogen for 2 h. The reaction mixture was cooled to room temperature. To the reaction was then added 2,4-diisopropyldibenzo[b,d]furan-3-amine (6 g, 22.44 mmol). The reaction was refluxed for 16 h. After cooled to room temperature, the precipitate was collected by filtration, and washed thoroughly with toluene and hexanes. Sodium hydroxide solution was added to the solid and then ethyl acetate. The organic layer was separated and dried over MgSO4. The solvent was evaporated. 7.4 g (83% yield) of product was obtained.

Aufarbeitung

  1. temperatureThe reaction was refluxed for 16 h
  2. temperatureAfter cooled to room temperature
  3. filtrationthe precipitate was collected by filtration
  4. washwashed thoroughly with toluene and hexanes
  5. additionSodium hydroxide solution was added to the solid
  6. customThe organic layer was separated
  7. dry with materialdried over MgSO4
  8. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-b7fdeb8f05e64ddeb4cd771af24e1b39
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156870B2

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