Sodium Bicarbonate → HCID 178450044, compound

HRID 1368551Notes

Reaction equation

HRID 1368551 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([C:17]1[N:18]=[CH:19][N:20](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:21]=1)([OH:16])[CH:13]([CH3:15])[CH3:14])[CH:6]=[CH:5]2.Cl.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([C:17]1[N:18]=[CH:19][NH:20][CH:21]=1)([OH:16])[CH:13]([CH3:15])[CH3:14])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 22018349HCID 22018349, compound

Product 1

HCID 178450044HCID 178450044, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

1-(6-Bromonaphthalen-2-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (1.0 g) and pyridine hydrochloride (390 mg) were dissolved in methanol (8 ml). The solution was stirred at 60° C. for 2 h. The solution was cooled and neutralized with saturated aqueous solution of sodium hydrogencarbonate. The solvent was distilled off and the residue was filtered and washed with ethanol. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (eluent, dichloromethane:methanol=30:1→10:1), then recrystallized from ethyl acetate to give the titled compound (454 mg) as a colorless powder.

Workup

  1. temperatureThe solution was cooled
  2. distillationThe solvent was distilled off
  3. filtrationthe residue was filtered
  4. washwashed with ethanol
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography (eluent, dichloromethane:methanol=30:1→10:1)
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8da5997004594b1e860ee04f11a5ddc9
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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