Trityl chloride → 5-Methyl-4-phenyl-1-trityl-1h-imidazole

HRID 2104961Notes

Reaction equation

HRID 2104961 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1[N:3]([C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:4]=[N:5][C:6]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 6456Trityl chlorideHCID 178418762HCID 178418762, compound

Product 1

HCID 688151645-Methyl-4-phenyl-1-trityl-1h-imidazoleYield 79.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-methyl-5-phenylimidazole (250 mg, 1.58 mmol) in 5 mL DMF at rt, were added TEA (242 μL, 1.74 mmol) and TrCl (485 mg, 1.74 mmol). The mixture was stirred at rt for 20 h, then was diluted with EtOAc, washed with H2O (2×) and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 50% EtOAc/hexanes gradient) to afford 504 mg of Intermediate 20.1 as a white solid.

Workup

  1. washwashed with H2O (2×) and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography (0 to 50% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-a3fa92ccce7c43c4ba107ea920e79554
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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