Trityl chloride → HCID 68815157, compound

HRID 2105003Notes

Reaction equation

HRID 2105003 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2[NH:6][CH:7]=[N:8][C:4]=2[CH:3]=1.Cl[C:12]([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>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]([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:7]=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 6456Trityl chlorideHCID 178477907HCID 178477907, compound

Product 1

HCID 68815157HCID 68815157, compoundYield 44.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloro-1H-benzo[d]imidazole (500 mg, 3.28 mmol) in 5 mL DMF, were added TEA (0.502 mL, 3.60 mmol) and TrCl (1.00 g, 3.60 mmol). The mixture was stirred at rt for 3 h, then was diluted with EtOAc. The organic phase was washed with H2O (2×) and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 75% EtOAc/hexanes gradient) to afford 580 mg of 5-chloro-1-trityl-1H-benzo[d]imidazole, followed by 225 mg of 6-chloro-1-trityl-1H-benzo[d]imidazole (177.1) as a white solid.

Workup

  1. washThe organic phase was washed with H2O (2×) and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography (0 to 75% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-945c5aae4e5b40ddaf3ff70f4555eeb0
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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