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

HRID 1750906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1750906
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:30]2[C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[O:27][C:26]=2[CH:25]=[C:24]([CH:35]([CH3:37])[CH3:36])[C:23]=1[NH2:38])([CH3:21])[CH3:20]>C1(C)C=CC=C(C)C=1>[CH:19]([C:22]1[C:30]2[C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[O:27][C:26]=2[CH:25]=[C:24]([CH:35]([CH3:37])[CH3:36])[C:23]=1[N:38]1[CH2:2][CH2:3][N:4]=[C:5]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:21])[CH3:20]

Komponenten

5

Edukt 3

HCID 24819Phosphorus pentachlorideHCID 101439N-(2-chloroethyl)benzamideHCID 584009881,3-Diisopropyldibenzo[b,d]furan-2-amine

Produkt 1

HCID 584008841-(1,3-diisopropyldibenzo[b,d]furan-2-yl)-2-phenyl-4,5-dihydro-1H-imidazoleAusbeute 54,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7929M-XyleneLösungsmittel2×

Versuchsvorschrift

N-(2-chloroethyl)benzamide (4.09 g, 22.27 mmol) and 90 mL m-xylene were added to a 250 ml, round-bottom flask. Next, phosphorus pentachloride (6.96 g, 33.4 mmol) was added carefully. The reaction mixture was heated to reflux under nitrogen for 2 h. The reaction mixture was cooled down to room temperature and 1,3-diisopropyldibenzo[b,d]furan-2-amine (6.55 g, 24.50 mmol) in 30 mL m-xylene was added. The reaction mixture was refluxed overnight under nitrogen. The reaction mixture was cooled in an ice bath. White solid was collected by filtration. The solid was washed with hexanes, dissolved in ethyl acetate, and washed twice with 10% sodium hydroxide solution. The organic layer was dried over magnesium sulfate, filtered, evaporated to a white solid which was dried under vacuum. 4.78 g (54% yield) of product was obtained.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under nitrogen for 2 h
  3. temperatureThe reaction mixture was refluxed overnight under nitrogen
  4. temperatureThe reaction mixture was cooled in an ice bath
  5. filtrationWhite solid was collected by filtration
  6. washThe solid was washed with hexanes
  7. dissolutiondissolved in ethyl acetate
  8. washwashed twice with 10% sodium hydroxide solution
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated to a white solid which
  12. customwas dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f508d6818bcf433cb080cf7b5985240b
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156870B2

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