Hydrochloric Acid → SB 203580, Sulfone

HRID 2257382Notes

Reaction equation

HRID 2257382 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:27])=[O:26])=[CH:21][CH:20]=3)[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.Cl.O.[O-:30][Mn](=O)(=O)=O.[K+].[O-]S([O-])=O.[Na+].[Na+].Cl.[OH-].[Na+]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:27])(=[O:30])=[O:26])=[CH:21][CH:20]=3)[NH:11][C:12]=2[C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 176155SB203580HCID 516875Potassium Permanganate2×HCID 21885828Hydrate;hydrochloride

Product 1

HCID 6610350SB 203580, SulfoneYield 16.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-(4-fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)-1H-imidazole (3.7 g, 9.8 mmol) [See Ex. 20 below] in 1:10 3N HCl/H2O (88 mL) was added a solution of KMnO4 (1.5 g, 9.8 mmol) in H2O (15 mL). After stirring at rt for 1 h, additional KMnO4 (0.15 g, 0.9 mmol) was added, and stirring was continued for 15 min. The mixture was then poured into saturated aqueous Na2SO3 (200 mL), and the pH was adjusted to slightly acidic by the addition of 3N HCl, then to neutral by the addition of 2.5N NaOH. The solid which formed was collected by filtration, washed successively with H2O and MeOH and recrystallized three times from MeOH to afford the title compound (0.63 g, 16%): mp 148°-149° C.

Workup

  1. stirringstirring
  2. waitwas continued for 15 min
  3. customThe solid which formed
  4. filtrationwas collected by filtration
  5. washwashed successively with H2O and MeOH
  6. customrecrystallized three times from MeOH

Sources & evidence

ORD record
ord-9a8f2d2de2f14efd99b57364f0483418
Source dataset
uspto-grants-1997_08
Patent number
US05656644

Reaction notes

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