Trityl chloride → 4,5-Diphenyl-1-tritylimidazole

HRID 2104959Notes

Reaction equation

HRID 2104959 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](Cl)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([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(Cl)Cl.CCOC(C)=O>[C:1]1([C:7]2[N:8]=[CH:9][N:10]([C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 6456Trityl chlorideHCID 695884,5-Diphenylimidazole

Product 1

HCID 41804394,5-Diphenyl-1-tritylimidazoleYield 65.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4,5-diphenylimidazole (500 mg, 2.27 mmol) in 5 mL CH2Cl2 at rt were added TEA (348 μL, 2.50 mmol) and trityl chloride (664 mg, 2.38 mmol). The mixture was stirred at rt for 18 h, then was diluted with EtOAc, washed with H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 30% EtOAc/hexanes gradient) to afford 692 mg of Intermediate 19.1 as a pale green solid.

Workup

  1. washwashed with H2O and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography (0 to 30% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-ae8f45b4c8f243989589de6541fbdf7a
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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