Sodium Hydroxide → 4-[4-[2-[(methylsulfonyl)methyl]-1H-imidazol-1-yl]butyl]phenol

HRID 1610952Notes

Reaction equation

HRID 1610952 reaction equation
[OH:1]OS([O-])=O.[K+].[CH3:7][S:8][CH2:9][C:10]1[N:11]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)[CH:12]=[CH:13][N:14]=1.[OH-:26].[Na+]>CO.O>[CH3:7][S:8]([CH2:9][C:10]1[N:11]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=2)[CH:12]=[CH:13][N:14]=1)(=[O:1])=[O:26]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 222593474-[4-[2-[(methylthio)methyl]-1H-imidazol-1-yl]butyl]phenolHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 222592974-[4-[2-[(methylsulfonyl)methyl]-1H-imidazol-1-yl]butyl]phenol

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Oxone (Trade mark; potassium peroxymonosulfate: 28.8 g) was added to a suspension of 4-[4-[2-[(methylthio)methyl]-1H-imidazol-1-yl]butyl]phenol (8.64 g) in methanol-water (2:1) (150 ml) at 0° C. and the mixture was stirred at room temperature for 3.5 hr. The reaction mixture was adjusted to pH 6 by addition of 4N aqueous sodium hydroxide solution to precipitate crystals, which were collected by filtration. The crystals were dissolved in ethyl acetate-methanol (1:4), and the insoluble was filtered off. The filtrated was concentrated and recrystallized from ethyl acetate-methanol-hexane to give the titled compound (6.53 g) as colorless needle crystals.

Workup

  1. customto precipitate crystals, which
  2. filtrationwere collected by filtration
  3. dissolutionThe crystals were dissolved in ethyl acetate-methanol (1:4)
  4. filtrationthe insoluble was filtered off
  5. concentrationThe filtrated was concentrated
  6. customrecrystallized from ethyl acetate-methanol-hexane

Sources & evidence

ORD record
ord-db391cbd504b442b8a212870d70892af
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

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