Anisole → HCID 22130792, compound

HRID 1416031Notes

Reaction equation

HRID 1416031 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)=[CH:13][N:12]=[C:11]1[CH2:23][O:24][Si](C(C)(C)C)(C)C)C1C=CC=CC=1.C1(OC)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O>[Cl:22][C:18]1[CH:17]=[C:16]([S:15][C:14]2[NH:10][C:11]([CH2:23][OH:24])=[N:12][CH:13]=2)[CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 22130072HCID 22130072, compound

Product 1

HCID 22130792HCID 22130792, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-benzyloxymethyl-2-t-butyldimethylsilyloxymethyl-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-b3a829f4e55944f89be165853b847606
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

Loading…