Reaktion #1915550

Reaktionsgleichung

1,3-diiodo-5,5-dimethylhydantoin

methyl 2-(1,1-dimethyl-2-methylsulfinylethylaminocarbonyl)benzoate

N-methylpyrrolidone

→

methyl 3-iodo-2-(1,1-dimethyl-2-methylsulfinylethylaminocarbonyl)-benzoate

Ausbeute 137.3%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture thus obtained
2. 2
   Temperaturwas heated
3. 3
   SonstigeAfter completion of the reaction
4. 4
   Temperaturthe reaction mixture was cooled to room temperature
5. 5
   Extraktionthe objective product was extracted with ethyl acetate
6. 6
   WaschenThe organic layer was washed successively with aqueous solution of sodium thiosulfate and saturated aqueous solution of sodium chloride
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONBy distilling off the solvent under reduced pressure
9. 9
   Sonstigea crude product was obtained
10. 10
    SonstigePurification of the crude product by silica gel column chromatography (ethyl acetate/n-hexane=1/3)

Vorschrift

Into the same reactor as in Example 1 were charged 1.5 mg of palladium acetate, 0.83 g of 1,3-diiodo-5,5-dimethylhydantoin, 1.0 g of methyl 2-(1,1-dimethyl-2-methylsulfinylethylaminocarbonyl)benzoate and 5 ml of N-methylpyrrolidone. The mixture thus obtained was heated with stirring at 90° C. for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and poured into water, and the objective product was extracted with ethyl acetate. The organic layer was washed successively with aqueous solution of sodium thiosulfate and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. By distilling off the solvent under reduced pressure, a crude product was obtained. Purification of the crude product by silica gel column chromatography (ethyl acetate/n-hexane=1/3) gave 1.27 g of methyl 3-iodo-2-(1,1-dimethyl-2-methylsulfinylethylaminocarbonyl)-benzoate (yield 89.1%, melting point 150.7–151.8° C.).

Quelle