Trityl chloride → 4-iodo-2-methyl-1-trityl-1H-imidazole

HRID 216310Notes

Reaction equation

HRID 216310 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.[I:28][C:29]1[N:30]=[C:31]([CH3:34])[NH:32][CH:33]=1>C(Cl)Cl>[I:28][C:29]1[N:30]=[C:31]([CH3:34])[N:32]([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:33]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178433060HCID 178433060, compound

Product 1

HCID 109504214-iodo-2-methyl-1-trityl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (13.4 mL, 96.2 mmol) followed by trityl chloride (20.1 g, 72.1 mmol) were added to an ambient temperature solution of 4-iodo-2-methyl-1H-imidazole (ca. 10 g, 48.1 mmol) in methylene chloride (90 mL). After stirring at ambient temperature for 2 days, the reaction mixture was diluted with methylene chloride and washed with water and brine, dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-15% acetone/methylene chloride afforded the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-24903aa7b6524069a4fdd268499310c2
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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