Hydrochloric Acid → HCID 178505025, compound

HRID 618264Notes

Reaction equation

HRID 618264 reaction equation
C([N:20]1[CH:24]=[C:23]([CH2:25][O:26][C:27]2[CH:28]=[C:29]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[CH:30]=[CH:31][CH:32]=2)[N:22]=[CH:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl>C(#N)C>[NH:20]1[CH:24]=[C:23]([CH2:25][O:26][C:27]2[CH:28]=[C:29]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[CH:30]=[CH:31][CH:32]=2)[N:22]=[CH:21]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69352185HCID 69352185, compound

Product 1

HCID 178505025HCID 178505025, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-[3-(1-trityl-1H-imidazol-4-ylmethoxy)-phenyl]methanesulfonamide (0.63 g, from above) and 1N HCl (10 mL) in acetonitrile (10 mL) was stirred at room temperature overnight. The solvent was removed and the residue was brought to basic pH with saturated potassium carbonate solution. The mixture was extracted with dichloromethane, washed with brine and dried over sodium sulfate. After evaporation of the solvent, the residue was chromatographed on silica gel eluting with methanol (containing 2% NH4OH)/dichloromethane (7:93) to give N-(3-(1H-imidazol-4-ylmethoxy)-phenyl]methanesulfonamide. This was converted to N-[3-(1H-imidazol-4-ylmethoxy)-phenyl]methanesulfonamide oxalate salt, mp 178-180° C. by treating with 1M oxalic acid in ether.

Workup

  1. customThe solvent was removed
  2. extractionThe mixture was extracted with dichloromethane
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was chromatographed on silica gel eluting with methanol (containing 2% NH4OH)/dichloromethane (7:93)

Sources & evidence

ORD record
ord-273a7aa64188421ea6433fcae60b5b93
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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