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

HRID 1750921Notes

Reaction equation

HRID 1750921 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.[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[C:25]([NH2:35])=[C:24]([CH:36]([CH3:38])[CH3:37])[CH:23]=1)([CH3:21])[CH3:20]>C1(C)C(C)=CC=CC=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[C:25]([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:24]([CH:36]([CH3:38])[CH3:37])[CH:23]=1)([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 101439N-(2-chloroethyl)benzamideHCID 584009571,3-Diisopropyldibenzo[b,d]furan-4-amine

Product 1

HCID 584010321-(1,3-diisopropyldibenzo[b,d]furan-4-yl)-2-phenyl-4,5-dihydro-1H-imidazoleYield 55.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

N-(2-chloroethyl)benzamide (6.3 g, 34 mmol) and PCl5 (7.9 g, 38 mmol) were suspended in xylene (75 mL) and refluxed for two hours. Then 1,3-diisopropyldibenzo[b,d]furan-4-amine (10 g, 38 mmol) was added. The mixture was refluxed overnight. After cooling by ice-bath, no precipitation was observed. The mixture was concentrated and the residue was washed with small amount of toluene and hexane. The crude 1-(1,3-diisopropyldibenzo[b,d]furan-4-yl)-2-phenyl-4,5-dihydro-1H-imidazole (7.5 g, 19 mmol, 54.8% yield) was used without further purification for the next step.

Workup

  1. temperaturerefluxed for two hours
  2. temperatureThe mixture was refluxed overnight
  3. temperatureAfter cooling by ice-bath
  4. customno precipitation
  5. concentrationThe mixture was concentrated
  6. washthe residue was washed with small amount of toluene and hexane

Sources & evidence

ORD record
ord-f0de1c6066184c28b691f80f4b83c027
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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