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

HRID 893300

반응식

HRID 893300 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9af403274bec48f084c833b46f71d2c8
출처 데이터셋
uspto-grants-1992_06
특허 번호
US05124327

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