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

HRID 1750901Notes

Reaction equation

HRID 1750901 reaction equation
[CH:1]([C:4]1[C:16]([N:17]2[CH2:21][CH2:20][N:19]=[C:18]2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:15]([CH:28]([CH3:30])[CH3:29])[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=1)([CH3:3])[CH3:2].[Mn]([O-])(=O)(=O)=O.[K+]>C(#N)C.ClCCl>[CH:1]([C:4]1[C:16]([N:17]2[CH:21]=[CH:20][N:19]=[C:18]2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:15]([CH:28]([CH3:30])[CH3:29])[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 584008541-(2,4-diisopropyldibenzo[b,d]furan-3-yl)-2-phenyl-4,5-dihydro-1H-imidazole

Product 1

HCID 584008691-(2,4-diisopropyldibenzo[b,d]furan-3-yl)-2-phenyl-1H-imidazoleYield 72%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

1-(2,4-diisopropyldibenzo[b,d]furan-3-yl)-2-phenyl-4,5-dihydro-1H-imidazole (7.4 g, 18.66 mmol) was dissolved in 200 mL of acetonitrile and 100 mL of dichloromethane. Potassium Permanganate (5.90 g, 37.3 mmol) and Clay K10 (12 g, 30.7 mmol) were ground in a mortar. The solid was then added carefully to the solution. Heat was generated after a few minutes. The reaction was monitored by TLC. The reaction was quenched with methanol after 1.5 h. The reaction mixture was filtered through Celite. The solvent was evaporated and the residue was purified by column. 5.3 g (72% yield) of pure product was obtained.

Workup

  1. additionThe solid was then added carefully to the solution
  2. temperatureHeat
  3. waitwas generated after a few minutes
  4. customThe reaction was quenched with methanol after 1.5 h
  5. filtrationThe reaction mixture was filtered through Celite
  6. customThe solvent was evaporated
  7. customthe residue was purified by column

Sources & evidence

ORD record
ord-d640ad05ac1942e29ea79d3538c0a3a5
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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