Sodium methanethiolate → 5-(4-Methoxy-benzoyl)-2-methylsulfanyl-benzenesulfonamide

HRID 1810158Notes

Reaction equation

HRID 1810158 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:18]([NH2:21])(=[O:20])=[O:19].[CH3:22][S-:23].[Na+]>O1CCOCC1>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([S:23][CH3:22])=[C:3]([S:18]([NH2:21])(=[O:20])=[O:19])[CH:4]=2)=[O:17])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 442352782-Fluoro-5-(4-methoxy-benzoyl)-benzenesulfonamide

Product 1

HCID 442355065-(4-Methoxy-benzoyl)-2-methylsulfanyl-benzenesulfonamideYield 68%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-fluoro-5-(4-methoxy-benzoyl)-benzenesulfonamide (0.15 g, 0.48 mmol) dissolved in dioxane (3 mL) is added sodium thiomethoxide (0.041 g, 0.57 mmol). The reaction mixture is heated at 90° C. for 4 h and then cooled to room temperature and concentrated in vacuo. The residue is partitioned between water and methylene chloride, and the aqueous phase 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 (50% ethyl acetate-hexane) gives 0.11 g (68%) of the title compound as a white solid. 1H NMR (CDCl3): δ 8.4 (d, J=2 Hz, 1H), 7.90 (dd, J=8, 2 Hz, 1H), 7.80 (d, J=9 Hz, 2H), 7.50 (d, J=8 Hz, 1H), 7.00 (d, J=9 Hz, 2H), 5.20 (s, 2H), 3.90 (s, 3H), 2.65 (s, 3H). Analytics calculated for C15H15NO4S2: C, 53.04; H, 4.48; N, 4.15. Found: C, 52.67; H, 4.57; N, 4.08. MS (m/z): 336 (M−1).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue is partitioned between water and methylene chloride
  4. extractionthe aqueous phase is extracted with methylene chloride three times
  5. washThe combined organic extracts are washed with a saturated sodium chloride solution
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification by silica gel chromatography (50% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-134a9d3feece4cd0bfdef31314f5d421
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

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