Reaktion #1929010

ord-dccb3fd262534e74a93075e8371d8868

Reaktionsgleichung

O=S([O-])O.[Na+]
sodium bisulfite
O=S(=O)([O-])c1cc2ccccc2[nH]1.[Na+]
sodium indole-2-sulfonate
CC(=O)OC(C)=O
acetic anhydride
→
CC(=O)n1c(S(=O)(=O)[O-])cc2ccccc21.[Na+]
sodium 1-acetylindole-2-sulfonate
Ausbeute 93.0%

Edukte

O=S([O-])O.[Na+]
sodium bisulfite
O=S(=O)([O-])c1cc2ccccc2[nH]1.[Na+]
sodium indole-2-sulfonate
CC(=O)OC(C)=O
acetic anhydride

Reagenzien

Keine

Reaktionsbedingungen

Temperatur
70°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe mixture was heated
  2. 2
    workup.WAITat 90° C. for 2 hrs
  3. 3
    TemperaturUpon cooling
  4. 4
    Filtrationthe solid was filtered
  5. 5
    Waschenwashed with ether
  6. 6
    Sonstigedried

Vorschrift

To a round-bottom-flask containing 60 mL acetic anhydride was added 5 g sodium bisulfite and 5 g sodium indole-2-sulfonate. The mixture was heated and stirred at 70° C. for 1 hr and then at 90° C. for 2 hrs. Upon cooling, the solid was filtered, washed with ether, and dried to yield 5.7 g of sodium 1-acetylindole-2-sulfonate product (93%) as a white solid. The sodium 1-acetylindole-2-sulfonate product was used in the next step without further purification. MP>320° C.; IR (KBr, cm−1) 3480, 3010, 1660, 1490, 1400, 1385, 1150, 1050, 980, 760.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08945397B2uspto-grants-2015_02