Reaktion #426672

ord-020593f2c3df42c3995f170760703ab1

Reaktionsgleichung

N#[C][Fe-3]([C]#N)([C]#N)([C]#N)([C]#N)[C]#N.[K+].[K+].[K+]
Potassium ferricyanide
NC(=S)c1ccccc1
thiobenzamide
c1ccc2scnc2c1
benzothiazole
NC(=S)c1ccccc1
thiobenzamide
[Na+].[OH-]
NaOH
N#[C][Fe-3]([C]#N)([C]#N)([C]#N)([C]#N)[C]#N.[K+].[K+].[K+]
potassium ferricyanide
→
N#[C][Fe-3]([C]#N)([C]#N)([C]#N)([C]#N)[C]#N.[K+].[K+].[K+].c1ccc2scnc2c1
benzothiazole
N#[C][Fe-3]([C]#N)([C]#N)([C]#N)([C]#N)[C]#N.[K+].[K+].[K+].c1ccc2scnc2c1
Potassium Ferricyanide Benzothiazole

Edukte

N#[C][Fe-3]([C]#N)([C]#N)([C]#N)([C]#N)[C]#N.[K+].[K+].[K+]
Potassium ferricyanide
NC(=S)c1ccccc1
thiobenzamide
c1ccc2scnc2c1
benzothiazole
NC(=S)c1ccccc1
thiobenzamide
[Na+].[OH-]
NaOH
N#[C][Fe-3]([C]#N)([C]#N)([C]#N)([C]#N)[C]#N.[K+].[K+].[K+]
potassium ferricyanide

Reagenzien

Keine

Lösungsmittel

O
water

Reaktionsbedingungen

Temperatur
5°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeIn this reaction
  2. 2
    SonstigeIn a typical reaction
  3. 3
    FiltrationThe mixture is filtered
  4. 4
    Waschenthe solid washed with H2O
  5. 5
    workup.DISSOLUTIONThe solid is dissolved in DCM (20 vol)
  6. 6
    Trocknendried (Na2SO4)
  7. 7
    Sonstigethe solvent removed under reduced pressure

Vorschrift

In this reaction, a thiobenzamide is converted to a benzothiazole in the presence of potassium ferricyanide. In a typical reaction, a thiobenzamide (1 equiv) is dissolved in NaOH (1.5 M, 39 equiv.) and the solution cooled to 5° C. with ice. Potassium ferricyanide in water (20%, 15 vol) is added and the reaction stirred at it for 18 h. The mixture is filtered and the solid washed with H2O. The solid is dissolved in DCM (20 vol), dried (Na2SO4) and the solvent removed under reduced pressure to give the crude benzothiazole product. Column chromatography may be carried out in order to obtain the pure target material.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08895313B2uspto-grants-2014_11