5,6-Dimethylbenzimidazole → 5,6-dimethyl-1-trityl-1H-benzo[d]imidazole

HRID 2105078Notes

Reaction equation

HRID 2105078 reaction equation
[CH3:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]2[NH:6][CH:7]=[N:8][C:4]=2[CH:3]=1.[C:12](Cl)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]2[N:6]([C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 6755,6-DimethylbenzimidazoleHCID 6456Trityl chloride

Product 1

HCID 688140645,6-dimethyl-1-trityl-1H-benzo[d]imidazoleYield 98.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5,6-dimethyl-1H-benzo[d]imidazole (500 mg, 3.42 mmol), trityl chloride (1.05 g, 3.76 mmol) and TEA (524 μL, 3.76 mmol) in 5 mL DMF was stirreds at rt for 3 h. The mixture was diluted with EtOAc, washed with H2O and brine, dried (Na2SO4) and concentrated. The crude residue was purified by flash chromatography (0 to 100% EtOAc/hexanes gradient) to afford 1.31 g of Intermediate 415.1.

Workup

  1. customat rt
  2. customfor 3 h
  3. washwashed with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash chromatography (0 to 100% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-8050a1119bad45ec8b22deed5851d011
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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