m-Chloroperbenzoic acid → HCID 86753583, compound

HRID 343086Notes

Reaction equation

HRID 343086 reaction equation
[CH3:1][S:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1.C1C=C(Cl)C=C(C(OO)=[O:32])C=1.OS([O-])=O.[Na+]>ClCCl>[CH3:1][S:2]([C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1)=[O:32]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 86753582HCID 86753582, compound

Product 1

HCID 86753583HCID 86753583, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a chilled solution (-78° C.) of 4-[5-methylthio-3-phenylisoxazol-4-yl]benzenesulfonamide (Example 58) (0.256 g, 0.814 mmol) in dichloromethane (8 mL) was added MCPBA (0.234 g of 60% reagent, 0.814 mmol). After 1 hour, the reaction was warmed to 0° C. and held there for an additional hour. Dichloromethane (30 mL) and a solution of NaHSO3 were added and mixed for 5 minutes. The resulting mixture was extracted with ethyl acetate (20 mL) and the layers separated. The organic phase was washed with NaHSO3 solution and with NaHCO3 solution, dried over MgSO4, filtered and concentrated in vacuo yielding 4-[5-methylsulfinyl-3-phenylisoxazol-4-yl]benzenesulfonamide (0.107 g, 36%) as a pale yellow powder: mp 194°-204° C. 1H NMR (CDCl3 with DMSO6 /300 MHz) 7.98 (d, 2H, 8.46 Hz), 7.53-7.37 (m, 7H), 6.39 (s, 2H), 3.18 (s, 3H). FABLRMS m/z 363 (M+H). FABHRMS m/z 363.0480 (M+H, C16H15N2O4S2 requires 363.0473). Anal. Calc'd for C16H14N2O4S2 : C, 53.03; H, 3.89; N, 7.73. Found: C, 53.24; H, 3.96; N, 7.50.

Workup

  1. waitheld there for an additional hour
  2. additionmixed for 5 minutes
  3. extractionThe resulting mixture was extracted with ethyl acetate (20 mL)
  4. customthe layers separated
  5. washThe organic phase was washed with NaHSO3 solution and with NaHCO3 solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2cf96aed3e574ceea2d83d59be2b5b24
Source dataset
uspto-grants-1999_01
Patent number
US05859257

Reaction notes

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