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Sodium Bicarbonate → HCID 178450128, compound

HRID 1059144
Notes
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Reaction equation

HRID 1059144 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([C:19]3[N:20]=[CH:21][N:22](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:23]=3)([OH:18])[CH:15]([CH3:17])[CH3:16])[CH:9]=2)=[CH:4][CH:3]=1.Cl.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([C:19]3[N:20]=[CH:21][NH:22][CH:23]=3)([OH:18])[CH:15]([CH3:17])[CH3:16])[CH:9]=2)=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 186685501-(4'-chloro[1,1'-biphenyl]-3-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol

Product 1

HCID 178450128HCID 178450128, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

1-(4′-Chloro[1,1′-biphenyl]-3-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (0.71 g) and pyridine hydrochloride (0.25 g) were dissolved in methanol (20 ml), and the mixture was stirred at 60° C. for 2 h. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution and the mixture was concentrated. Water and ethyl acetate were added and the mixture was extracted with ethyl acetate. The organic layer was dried and concentrated, and the obtained residue was purified by silica gel column chomatography (eluent, dichloromethane:methanol=40:1). Recrystallization from hexane-ethyl acetate gave the title compound (0.31 g) as a colorless solid.

Workup

  1. concentrationthe mixture was concentrated
  2. additionWater and ethyl acetate were added
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customthe obtained residue was purified by silica gel column chomatography (eluent, dichloromethane:methanol=40:1)
  7. customRecrystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-a9692b3c177c41cc92753d35db0f7782
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06518257B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes