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

HRID 873631Notes

Reaction equation

HRID 873631 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. customThen, the 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-5d61946976c04b0e8754facb372d7ca8
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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