m-Chloroperbenzoic acid → 2-Methanesulfinyl-5-(4-methoxy-benzoyl)-benzenesulfonamide

HRID 1810159Notes

Reaction equation

HRID 1810159 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([C:7]([C:9]2[CH:10]=[CH:11][C:12]([S:19][CH3:20])=[C:13]([S:15]([NH2:18])(=[O:17])=[O:16])[CH:14]=2)=[O:8])=[CH:5][CH:4]=1.ClC1C=C(C=CC=1)C(OO)=[O:28]>C(Cl)Cl>[CH3:20][S:19]([C:12]1[CH:11]=[CH:10][C:9]([C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:22][CH:21]=2)=[CH:14][C:13]=1[S:15]([NH2:18])(=[O:17])=[O:16])=[O:28]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 442355065-(4-Methoxy-benzoyl)-2-methylsulfanyl-benzenesulfonamide

Product 1

HCID 442355072-Methanesulfinyl-5-(4-methoxy-benzoyl)-benzenesulfonamideYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(4-methoxy-benzoyl)-2-methylsulfanyl-benzenesulfonamide (0.06 g, 0.18 mmol) dissolved in methylene chloride (3 mL) at 0° C. is added m-chloroperoxybenzoic acid (0.061 g, 0.36 mmol). The reaction mixture is stirred at room temperature for 30 minutes Then, the reaction is quenched with saturated sodium sulfite and sodium bicarbonate solution. The aqueous layer is extracted with methylene chloride three times. The combined organic extracts are washed with a saturated sodium chloride solution, dried with magnesium sulfate, and concentrated in vacuo. Purification by silica gel chromatography (75% ethyl acetate-hexane) followed by recrystallization (methylene chloride-hexane) provides 0.022 g (35%) of the title compound as a pale yellow solid. 1H NMR (CDCl3): δ 8.35 (d, J=8 Hz, 1H), 8.10 (dd, J=8, 1 Hz, 1H), 7.80 (d, J=9 Hz, 2H), 7.00 (d, J=9 Hz, 2H), 5.60 (s, 2H), 3.95 (s, 3H), 3.00 (s, 3H). Analytics calculated for C15H15NO5S2: C, 50.98; H, 4.28; N, 3.96. Found: C, 50.17; H, 4.46; N, 3.40. MS (m/z): 352 (M−1).

Workup

  1. customthe reaction is quenched with saturated sodium sulfite and sodium bicarbonate solution
  2. extractionThe aqueous layer is extracted with methylene chloride three times
  3. washThe combined organic extracts are washed with a saturated sodium chloride solution
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography (75% ethyl acetate-hexane)
  7. customfollowed by recrystallization (methylene chloride-hexane)

Sources & evidence

ORD record
ord-e0400dc2934541a0a11dc33adb3cc652
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

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