Anisole → HCID 22130792, compound

HRID 1857730Notes

Reaction equation

HRID 1857730 reaction equation
C(OC[N:10]1[C:14]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)=[C:13](CO[SiH3])[N:12](C)[C:11]1([CH3:31])C(C)(C)C)C1C=CC=CC=1.C1([O:38]C)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].C(=O)([O-])O.[Na+]>[N+](C)([O-])=O.C(OCC)(=O)C.O>[Cl:22][C:18]1[CH:17]=[C:16]([S:15][C:14]2[NH:10][C:11]([CH2:31][OH:38])=[N:12][CH:13]=2)[CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 131722153HCID 131722153, compound

Product 1

HCID 22130792HCID 22130792, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6375NitromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-benzyloxymethyl-2-t-butyldimethyl-silyloxymethyl-5-(3-chlorophenylthio)imidazole (45) in nitromethane (108 ml) was added 14.7 g of (137 mmol) of anisole, and then, 18.1 g (136 mmol) of anhydrous aluminium chloride was gradually added at lower than 30° C. After completion of the addition, the mixture was stirred at room temperature for 15 minutes. The reaction mixture was cooled, and there were added water and a saturated aqueous sodium hydrogen carbonate solution to be alkaline. Ethyl acetate was added to the mixture, and the mixture was filtered on Hiflow Super Cell to separate. The organic layer was washed with water, dried over sodium sulfate, and the solvent was concentrated under reduced pressure. The residue was purified by silica gel chromatography (7% methanol-methylene chloride) to give 9.5 g of [5-(3-chlorophenylthio)-1H-imidazol-2-yl]methanol as oil (yield 87%).

Workup

  1. additionAfter completion of the addition
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe mixture was filtered on Hiflow Super Cell
  4. customto separate
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (7% methanol-methylene chloride)

Sources & evidence

ORD record
ord-caa05871520c43cd99c55f85ca0b1b5c
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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