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

HRID 1750907Notes

Reaction equation

HRID 1750907 reaction equation
[CH:1]([C:4]1[C:12]2[C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[O:9][C:8]=2[CH:7]=[C:6]([CH:17]([CH3:19])[CH3:18])[C:5]=1[N:20]1[CH2:24][CH2:23][N:22]=[C:21]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:3])[CH3:2].[Mn]([O-])(=O)(=O)=O.[K+].CO>C(#N)C.ClCCl>[CH:1]([C:4]1[C:12]2[C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[O:9][C:8]=2[CH:7]=[C:6]([CH:17]([CH3:19])[CH3:18])[C:5]=1[N:20]1[CH:24]=[CH:23][N:22]=[C:21]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 516875Potassium Permanganate2×HCID 584008841-(1,3-diisopropyldibenzo[b,d]furan-2-yl)-2-phenyl-4,5-dihydro-1H-imidazole

Product 1

HCID 584009131-(1,3-diisopropyldibenzo[b,d]furan-2-yl)-2-phenyl-1H-imidazoleYield 44.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

1-(1,3-diisopropyldibenzo[b,d]furan-2-yl)-2-phenyl-4,5-dihydro-1H-imidazole (4.78 g, 12.05 mmol) in 70 mL of acetonitrile and 70 mL of dichloromethane were added to a 1 L round bottom flask. Potassium permanganate (3.81 g, 24.11 mmol) was ground in a mortar and pestle. Monmorilonite K was added and was ground together finely with the potassium permanganate. This mixture was added to the solution in portions over 0.5 hours. Reaction was done 1 h after first addition. 100 mL of methanol was added and stirred for 1 h. The solid was filtered through Celite. The material was purified using a 200 g Varian column eluting with 20% ethyl acetate/hexanes. 2.1 g (44% yield) of product was obtained after column.

Workup

  1. additionMonmorilonite K was added
  2. additionThis mixture was added to the solution in portions over 0.5 hours
  3. customReaction
  4. additionafter first addition
  5. filtrationThe solid was filtered through Celite
  6. customThe material was purified
  7. washeluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-246bb99531064d9ab3b7bdf4d940d7aa
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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