Monoperoxyphthalic Acid Magnesium Salt → 1H-Indole, 2-[(phenylsulfinyl)methyl]-3-(phenylthio)-

HRID 260463Notes

Reaction equation

HRID 260463 reaction equation
[C:1]1([S:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[CH2:17][S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Mg+2].C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=[O:30]>CO>[C:19]1([S:18]([CH2:17][C:9]2[NH:10][C:11]3[C:16]([C:8]=2[S:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:30])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 10130449Monoperoxyphthalic Acid Magnesium SaltHCID 110462663-Phenylthio-2-phenylthiomethylindole

Product 1

HCID 4548451H-Indole, 2-[(phenylsulfinyl)methyl]-3-(phenylthio)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 3-phenylthio-2-phenylthiomethylindole (0.750 g, 2.94 mmol) in methanol (100 mL) was cooled to 0° C. with stirring. Monoperoxyphthalic acid magnesium salt (0.908 g, 80% peracid) in methanol (50 mL) was added slowly dropwise. After addition, the reaction was stirred an additional 30 min., then quenched with 10% aqueous sodium thiosulfate (2 mL). The methanol was removed in vacuo, and the residue partitioned between ethyl acetate and water. The organic phase was washed successively with water and saturated brine, then dried over magnesium sulfate. Filtration and concentration of the filtrate in vacuo gave an oil which was purified by chromatography on silica gel using 20-30% ethyl acetate in hexane. The title compound was obtained as a foam, mp 71°-74° C. Exact mass calculated for C21H17NOS2 : 364.082982. Found: 364.084549. NMR (DMSO-d6) δ11.82 (1H, s), 7.50 (6H, m), 7.23 (1H, d, J=8 Hz), 7.15 (3 H, m) 7.05 (2H, m) 6.90 2H, m), 4.43 (1, d, J=13 Hz), 4.38 (1H, d, J=13 Hz).

Workup

  1. additionAfter addition
  2. stirringthe reaction was stirred an additional 30 min.
  3. customquenched with 10% aqueous sodium thiosulfate (2 mL)
  4. customThe methanol was removed in vacuo
  5. customthe residue partitioned between ethyl acetate and water
  6. washThe organic phase was washed successively with water and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationFiltration and concentration of the filtrate in vacuo
  9. customgave an oil which
  10. customwas purified by chromatography on silica gel using 20-30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-959a80dd02dd4f3fa00c2562dc6f9af9
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

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