Reaktion #2334532

Reaktionsgleichung

N-acetylthiourea

Bromine

1-(3-Fluoro-4-methanesulfonyl-phenyl)-propan-2-one

1-bromo-1-(3-fluoro-4-methanesulfonyl-phenyl)-propan-2-one

→

title compound

N-[5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-acetamide

Lösungsmittel

ethanol

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis semi frozen
2. 2
   Temperaturfrozen state
3. 3
   Temperaturto warm to room temperature
4. 4
   Sonstigethe solvent is removed
5. 5
   Sonstigeto give a brown oil
6. 6
   workup.ADDITIONcontaining
7. 7
   workup.STIRRINGThe mixture is stirred at 60° C. for 30 minutes
8. 8
   Temperaturto cool whereupon the product
9. 9
   Sonstigecrystallised
10. 10
    FiltrationFiltration

Vorschrift

1-(3-Fluoro-4-methanesulfonyl-phenyl)-propan-2-one (Example 64c) (1.0 g, 4.34 mmol) is dissolved in dioxane (35 ml) and the solution is cooled to 10° C. at which point the mixture is semi frozen. Bromine (0.067 ml, 1.2 mmol, 0.3 eq.) is added slowly and the mixture is stirred for an additional 15 min in a semi frozen state. The mixture is then allowed to warm to room temperature and the solvent is removed to give a brown oil containing starting material and 1-bromo-1-(3-fluoro-4-methanesulfonyl-phenyl)-propan-2-one. This material is dissolved in ethanol (30 ml) and N-acetylthiourea (0.369 g, 3.1 mmol) is added in one portion. The mixture is stirred at 60° C. for 30 minutes then allowed to cool whereupon the product crystallised. Filtration affords the title compound as a white solid.

Quelle