Sodium Pyrosulfite → Benzenesulfonamide

HRID 2288898Notes

Reaction equation

HRID 2288898 reaction equation
CSC1OC([C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=C(C2C=CC=CC=2)N=1.OOS([O-])=O.[K+].S([O-])(O[O-])(=O)=O.[K+].[K+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(OCC)(=O)C.O.C(O)C>[C:17]1([S:20]([NH2:23])(=[O:22])=[O:21])[CH:18]=[CH:19][CH:14]=[CH:15][CH:16]=1

Participants

8

Reactant 4

HCID 656671Sodium PyrosulfiteHCID 10313463Potassium peroxymonosulphateHCID 18701492HCID 18701492, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 7370BenzenesulfonamideYield 132.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-[2-Methylthio-4-phenyl-5-oxazolyl]benzenesulfonamide (Example 50) (0.5 g, 1.44 mmol), ethanol (100 mL), water (50 mL), and Oxone® (potassium peroxymonosulfate, 0.88 g, 1.44 mmol) were stirred at room temperature for 16.0 hours. Sodium metabisulfite (5 g) and water (50 mL) were added and the resulting mixture stirred for 0.25 hours before the addition of ethyl acetate (200 mL). The organic layer was separated and washed with brine and water, dried over MgSO4 and concentrated. The residue was purified by flash chromatography eluting with ethyl acetate:hexanes (1:3). The first material collected was concentrated and recrystallized to yield 4-[2 -methylsulfonyl)-4-phenyl-5-oxzolyk]benzenesulfonamide as a white solid (0.3 g, 55%): mp 186-188° C. 1H NMR (DMSO-d6) 300 MHz δ 7.92 (d, J=8.5 Hz, 2H) 7.81 (d, J=8.5 Hz, 2H) 7.6 (m, 2H) 7.48 (m, 5H) 3.3 (s, 3H). Anal. Calc'd. for C16H14N2O5S2 : C, 50.78; H, 3.73; N, 7.40. Found: C, 50.79; H, 3.72; N, 7.38. The second material collected was concentrated and recrystallized to yield 4-[2-methylsulfinyl)-4-phenyl-5-oxazolyl]benzenesulfonamide as a white solid (0.16 g, 31%): mp 174-176° C. 1H NMR (DMSO-d6) 300 MHz δ 7.9 (d, J=8.5 Hz, 2H) 7.8 (d, J=8.5 Hz, 2H) 7.6 (m, 2H) 7.48 (m, 5H) 3.2 (s, 3H). Anal. Calc'd. for C16H14N2O4S2 : C, 53.03; H, 3.89; N, 7.73. Found: C, 53.08; H, 3.85; N, 7.66.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine and water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with ethyl acetate:hexanes (1:3)
  7. customThe first material collected
  8. concentrationwas concentrated
  9. customrecrystallized

Sources & evidence

ORD record
ord-66e929c58e054209b158299d99ef78a9
Source dataset
uspto-grants-2000_07
Patent number
US06090834

Reaction notes

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