Water → 4-Methyl-1-trityl-1H-imidazole

HRID 856764Notes

Reaction equation

HRID 856764 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.C(N(CC)CC)C.[C:14]1([C:20]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)Cl)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C=O)C>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178418800HCID 178418800, compound

Product 1

HCID 6182544-Methyl-1-trityl-1H-imidazoleYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-methylimidazole (20.0 g) and triethylamine (53.5 ml) in DMF (300 ml), a solution of triphenylchloromethane (71.3 g) in DMF (200 ml) was added dropwise at 0° C. under nitrogen atmosphere. After finishing the dropping, and the mixture was allowed to be at room temperature and the mixture was stirred overnight. Water was added to the mixture, and the precipitated solid was collected by filtration. The obtained solid was washed with water twice and dried under reduced pressure, to give 4-methyl-1-triphenylmethylimidazole (79.1 g) as colorless solid.

Workup

  1. customto be at room temperature
  2. filtrationthe precipitated solid was collected by filtration
  3. washThe obtained solid was washed with water twice
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-b7c0b463fb484751b5f5e2fc0c78527a
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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