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Dichloromethane → 1-(1,3-diisopropyldibenzo[b,d]furan-4-yl)-2-phenyl-1H-imidazole

HRID 1750922
Notes
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Reaction equation

HRID 1750922 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3].ClCCl.[CH:28]([C:31]1[C:39]2[C:38]3[CH:40]=[CH:41][CH:42]=[CH:43][C:37]=3[O:36][C:35]=2[C:34]([N:44]2[CH2:48][CH2:47][N:46]=[C:45]2[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[C:33]([CH:55]([CH3:57])[CH3:56])[CH:32]=1)([CH3:30])[CH3:29]>C(#N)C>[CH:28]([C:31]1[C:39]2[C:38]3[CH:40]=[CH:41][CH:42]=[CH:43][C:37]=3[O:36][C:35]=2[C:34]([N:44]2[CH:48]=[CH:47][N:46]=[C:45]2[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[C:33]([CH:55]([CH3:57])[CH3:56])[CH:32]=1)([CH3:30])[CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 516875Potassium PermanganateHCID 584010321-(1,3-diisopropyldibenzo[b,d]furan-4-yl)-2-phenyl-4,5-dihydro-1H-imidazoleHCID 71586775Bentonite

Product 1

HCID 584009471-(1,3-diisopropyldibenzo[b,d]furan-4-yl)-2-phenyl-1H-imidazoleYield 37.3%

Reagents, catalysts & solvents

1
HCID 6342AcetonitrileSolvent

Procedure

The potassium permanganate (5.58 g, 35.3 mmol) and Montmorillonite K-10 clay (10 g) were mixed and finely grounded. The mixture was slowly (about 15 minutes) added into the mixed solution of dichloromethane (50 mL), acetonitrile (150 mL) and 1-(1,3-diisopropyldibenzo[b,d]furan-4-yl)-2-phenyl-4,5-dihydro-1H-imidazole (7 g, 17.6 mmol), which was cooled by ice bath. Then the reaction was stirred for another hour and quenched by adding 20 mL of ethanol. Filtered through a Celite plug. The crude product was purified by silica gel column (up to 30% EtOAc in hexanes) and recrystallization from hexane. 1-(1,3-diisopropyldibenzo[b,d]furan-4-yl)-2-phenyl-1H-imidazole (2.6 g, 6.57 mmol, 37.2% yield) was obtained as white solid (99.8% HPLC).

Workup

  1. custom(about 15 minutes)
  2. temperaturewas cooled by ice bath
  3. customquenched
  4. additionby adding 20 mL of ethanol
  5. filtrationFiltered through a Celite plug
  6. customThe crude product was purified by silica gel column (up to 30% EtOAc in hexanes) and
  7. customrecrystallization from hexane

Sources & evidence

ORD record
ord-b9cf82109cc14a8c9933ac1b97df14e6
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09156870B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes