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

HRID 893300

反応式

HRID 893300 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

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 (3H, m) 7.05 (2H, m) 6.90 2H, m), 4.43 (1H, d, J=13 Hz), 4.38 (1H, d, J=13 Hz).

後処理

  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

出典と根拠

ORDレコード
ord-9af403274bec48f084c833b46f71d2c8
出典データセット
uspto-grants-1992_06
特許番号
US05124327

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