Triethylamine → 4-(2,2-dimethylbutyl)-2-methyl-1-trityl-1H-imidazole

HRID 216316Notes

Reaction equation

HRID 216316 reaction equation
C(N(CC)CC)C.[C:8](Br)([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]([CH3:39])([CH2:37][CH3:38])[CH2:30][C:31]1[N:32]=[C:33]([CH3:36])[NH:34][CH:35]=1>C(Cl)Cl>[CH3:28][C:29]([CH3:39])([CH2:37][CH3:38])[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 8471TriethylamineHCID 11692BromotriphenylmethaneHCID 178442462HCID 178442462, compound

Product 1

HCID 591619684-(2,2-dimethylbutyl)-2-methyl-1-trityl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (34 mL, 0.24 mol) followed by trityl bromide (62 g, 0.19 mol) (portionwise) were added to a 0° C. solution of 4-(2,2-dimethylbutyl)-2-methyl-1H-imidazole (26.4 g, 0.16 mol) in methylene chloride (300 mL). After stirring at ambient temperature overnight, the reaction mixture was filtered and washed with water and brine, dried (magnesium sulfate), filtered and concentrated in vacuo. Chromatography over silica eluting with 10-40% ethyl acetate/hexane afforded the title compound.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washwashed with water and brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-22403f63ba6a4561aa1745b4fd1a6013
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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