Sodium Methoxide → N-[4-(1-Hydroxy-2-(1H-imidazol-1-yl)ethyl]phenyl]methanesulfonamide

HRID 1789481

Reaction equation

HRID 1789481 reaction equation
Cl.O[C:3]1[N:4]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][CH:11]=2)[CH:5]=[CH:6][N:7]=1.C[O-:22].[Na+]>CO>[OH:22][CH:9]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][CH:11]=1)[CH2:8][N:4]1[CH:5]=[CH:6][N:7]=[CH:3]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 178505018HCID 178505018, compound

Product 1

HCID 13763390N-[4-(1-Hydroxy-2-(1H-imidazol-1-yl)ethyl]phenyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Heat a mixture of 30.83 g (0.097 mole) of (±)-1-[2-hydroxy-2-[4-((methylsulfonyl)amino)phenyl]ethyl-1H-imidazole hydrochloride and 5.24 g (0.097 mole) of sodium methylate in 100 mL of methanol and filter hot through 300 g of alumina (Fisher, neutral, activity III). Wash the alumina with 20% methanol in methylene chloride (200 mL). Concentrate the filtrate in vacuo to afford the title compound.

Workup

  1. temperatureHeat
  2. filtrationfilter hot through 300 g of alumina (Fisher, neutral, activity III)
  3. washWash the alumina with 20% methanol in methylene chloride (200 mL)
  4. concentrationConcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-9c952c876e5e4332a35b6f1b55bcb233
Source dataset
uspto-grants-1987_08
Patent number
US04689341

Linked notes

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