Reaktion #1726699

ord-aa04fdcc077146b994e8fe3e603cbdf6

Reaktionsgleichung

CSc1nc(-c2ccccc2)c(N)s1
5-amino-2-(methylsulfanyl)-4-phenylthiazole
OO
hydrogen peroxide
CS(=O)c1nc(-c2ccccc2)c(N)s1
5-amino-2-(methylsulfinyl)-4-phenylthiazole
Ausbeute 87.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigedropwise at ambient temperature
  2. 2
    SonstigeAfter 4 hr the mixture was partitioned between dichloromethane (60 ml) and water (60 ml)
  3. 3
    SonstigeThe organic phase was separated
  4. 4
    Waschenwashed with brine
  5. 5
    Trocknendried over sodium sulfate
  6. 6
    Filtrationfiltered
  7. 7
    Einengenconcentrated in vacuo

Vorschrift

To 5-amino-2-(methylsulfanyl)-4-phenylthiazole (305 mg, 1.37 mmol) in acetic acid (3.0 ml) was added aqueous hydrogen peroxide (660 μl, 30% wt, 6.9 mmol) dropwise at ambient temperature. After 4 hr the mixture was partitioned between dichloromethane (60 ml) and water (60 ml). The organic phase was separated, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography on silica gel (ethyl acetate/hexanes) yielded pure 5-amino-2-(methylsulfinyl)-4-phenylthiazole (285 mg, 87%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08110568B2uspto-grants-2012_02