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

HRID 1750925Notes

Reaction equation

HRID 1750925 reaction equation
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.[CH2:19]([C:23]1[C:35]([NH2:36])=[C:34]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:26]2[O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:25]=2[CH:24]=1)[CH:20]([CH3:22])[CH3:21]>C1(C)C=CC=C(C)C=1>[CH2:19]([C:23]1[C:35]([N:36]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:34]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:26]2[O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:25]=2[CH:24]=1)[CH:20]([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 101439N-(2-chloroethyl)benzamideHCID 584010632,4-Diisobutyldibenzofuran-3-amine

Product 1

HCID 584009291-(2,4-diisobutyldibenzo[b,d]furan-3-yl)-2-phenyl-4,5-dihydro-1H-imidazoleYield 77%

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Procedure

N-(2-chloroethyl)benzamide (3.1 g, 16.88 mmol) was dissolved in 40 mL anhydrous m-xylene under nitrogen. Phosphorus pentachloride (5.27 g, 25.3 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-diisobutyldibenzo[b,d]furan-3-amine (5.49 g, 18.57 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 (5.5 g, 77%).

Workup

  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

Sources & evidence

ORD record
ord-a9b684a2ba3f4b76b6853098168e78de
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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