Trityl chloride → 4-Bromo-1-trityl-1H-imidazole

HRID 1176656Notes

Reaction equation

HRID 1176656 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[N:10]=[CH:11][NH:12][CH:13]=1.[C:14](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([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(=O)([O-])O.[Na+]>ClCCl>[Br:8][C:9]1[N:10]=[CH:11][N:12]([C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:13]=1

Participants

6

Reactant 4

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178418934HCID 178418934, compound

Product 1

HCID 27732744-Bromo-1-trityl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.3787 g of triethylamine is added dropwise over 15 minutes to a solution of 0.500 g of 4-bromoimidazole, 1.043 g of trityl chloride and 25 ml of dichloromethane. The reaction mixture is stirred at room temperature for 11 hours and then poured onto 50 ml of aqueous saturated sodium hydrogencarbonate solution. The mixture is extracted twice with 75 ml of dichloromethane. The combined organic phases are washed with 50 ml of brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a white solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.38 (1:3 EtOAc-heptane); Rt=5.02.

Workup

  1. extractionThe mixture is extracted twice with 75 ml of dichloromethane
  2. washThe combined organic phases are washed with 50 ml of brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-4835348da69c497998f5d0e5972d480c
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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