Trityl chloride → 4-(2,2-dimethylpropyl)-2-methyl-1-trityl-1H-imidazole

HRID 216319Notes

Reaction equation

HRID 216319 reaction equation
C(N(CC)CC)C.[C:8](Cl)([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)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:28][C:29]([CH3:38])([CH3:37])[CH2:30][C:31]1[N:32]=[C:33]([CH3:36])[NH:34][CH:35]=1>C(Cl)Cl>[CH3:28][C:29]([CH3:38])([CH3:37])[CH2:30][C:31]1[N:32]=[C:33]([CH3:36])[N:34]([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:35]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178432730HCID 178432730, compound

Product 1

HCID 591619634-(2,2-dimethylpropyl)-2-methyl-1-trityl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (70 mL, 0.5 mol) followed by trityl chloride (90 g, 0.32 mol) were added to an ambient temperature solution of 4-(2,2-dimethylpropyl)-2-methyl-1H-imidazole (49 g, 0.32 mmol) in methylene chloride (1 L). After stirring at ambient temperature for 30 min, the reaction mixture was washed with water and brine, dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 10-20% ethyl acetate/hexane afforded the title compound.

Workup

  1. washthe reaction mixture was washed with water and brine
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-daaf2e7af5f04d99bb1e037c381c7cfe
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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