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

HRID 1750912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1750912
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[CH:34]=[C:33]([CH:35]([CH3:37])[CH3:36])[C:25]2[O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:24]=2[C:23]=1[NH2:38])([CH3:21])[CH3:20]>C1(C)C=CC=C(C)C=1>[CH:19]([C:22]1[CH:34]=[C:33]([CH:35]([CH3:37])[CH3:36])[C:25]2[O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:24]=2[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 584010762,4-Diisopropyldibenzo[b,d]furan-1-amine

Produkt 1

HCID 584010671-(2,4-diisopropyldibenzo[b,d]furan-1-yl)-2-phenyl-4,5-dihydro-1H-imidazoleAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7929M-XyleneLösungsmittel

Versuchsvorschrift

N-(2-chloroethyl)benzamide (2.1 g, 11.2 mmol), PCl5 (3.5 g, 16.8 mmol) were dissolved in m-Xylene (100 mL) and refluxed for 2 h. After cooling down the reaction flask to room temperature, 2,4-diisopropyldibenzo[b,d]furan-1-amine (3.3 g, 12.3 mmol) was added to it and the reaction mixture was refluxed overnight. From the cooled reaction mixture white precipitate was filtered out. Precipitate was dissolved in ethylacetate and partitioned between ethylacetate and aqueous Na2CO3. Organic phase was extracted out and dried under vacuum. Target compound (4 g, 90% yield) was used in next step without further purification.

Aufarbeitung

  1. temperaturerefluxed for 2 h
  2. temperaturethe reaction mixture was refluxed overnight
  3. customFrom the cooled reaction mixture white precipitate
  4. filtrationwas filtered out
  5. dissolutionPrecipitate was dissolved in ethylacetate
  6. custompartitioned between ethylacetate and aqueous Na2CO3
  7. extractionOrganic phase was extracted out
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5e0b1c1a09db455f9220f5360161149f
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156870B2

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