Water → 4-phenyl-1-(triphenylmethyl)-1H-imidazole

HRID 2104949Notes

Reaction equation

HRID 2104949 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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.O>CN(C=O)C>[C:1]1([C:7]2[N:8]=[CH:9][N:10]([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:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6456Trityl chlorideHCID 178418822HCID 178418822, compound

Product 1

HCID 102217694-phenyl-1-(triphenylmethyl)-1H-imidazoleYield 72.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-phenylimidazole (500 mg, 3.47 mmol) in 5 mL DMF, were added TEA (508 μL, 3.64 mmol) and trityl chloride (1.06 g, 3.82 mmol). The mixture was stirred at rt for 15 h, then was poured into 50 mL H2O. The precipitate was collected by filtration and sucked dry, then was suspended in 20 mL Et2O. The suspension was filtered, rinsed with 5 mL Et2O, then vacuum dried to afford 974 mg of Intermediate 8.1 as a white solid.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customsucked dry
  3. filtrationThe suspension was filtered
  4. washrinsed with 5 mL Et2O
  5. customvacuum dried

Sources & evidence

ORD record
ord-90f87fb6db6e4edd87cd49aad470f934
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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