Toluene → 1-Benzyl-3-phenylsulfinylindole

HRID 1906936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1906936
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[C:10]1([S:16]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[CH2:7]([N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]([S:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:17])=[CH:19]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 134429343-(Benzenesulfinyl)-1H-indole

Produkt 1

HCID 134429351-Benzyl-3-phenylsulfinylindole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5963Benzyltrimethylammonium chlorideKatalysatorHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

A mixture of toluene (100 ml), 50% sodium hydroxide (20 ml), 3-phenylsulfinylindole (4.27 g, 17.7 mmol) and benzyltrimethylammonium chloride (6.01 g, 26.5 mmol) was vigorously stirred at reflux temperature for 4 hours. The organic phase was separated and combined with an ether extract of the aqueous phase. The extract was dried and evaporated in vacuo giving a solid which on crystallization from dichloromethane-hexane gave the solid product. Chromatography of the mother liquor on silica gel using hexane-ethyl acetate (3:2) as the eluant gave a further quantity of the title compound, m.p. 148°-149° C. identical to the material prepared in Example 8.

Aufarbeitung

  1. temperatureat reflux temperature for 4 hours
  2. customThe organic phase was separated
  3. extractionextract of the aqueous phase
  4. customThe extract was dried
  5. customevaporated in vacuo
  6. customgiving a solid which
  7. customon crystallization from dichloromethane-hexane
  8. customgave the solid product

Quellen und Nachweise

ORD-Eintrag
ord-1fe17a9ae9314e7d9f3e94b4acfc9259
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04654360

Notizen zur Reaktion

Wird geladen…