Reaktion #528076

Reaktionsgleichung

sodium hydroxide

N-bromosuccinimide

2-amino-3-cyano-6-methylpyrazine

→

2-amino-3-cyano-5-bromo-6-methylpyrazine

Lösungsmittel

N,N-dimethylformamide

N,N-dimethylformamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile maintaining the reaction mixture temperature at about 15°-25° C
2. 2
   workup.ADDITIONUpon completion of addition
3. 3
   FiltrationA solid precipitate is collected by filtration
4. 4
   Sonstigedried under reduced pressure

Vorschrift

A stirred solution of 8.5 grams (0.063 mole) of 2-amino-3-cyano-6-methylpyrazine [prepared by the method of Taylor and Kobayashi; JOC, 41, 299 (1976)]in 125 mL of N,N-dimethylformamide is cooled in an ice bath, and a solution of 11.2 grams (0.063 mole) of N-bromosuccinimide in 125 mL of N,N-dimethylformamide is added dropwise during a 30 minute period, while maintaining the reaction mixture temperature at about 15°-25° C. Upon completion of addition, the reaction mixture is stirred at ambient temperature for about 20 hours. After this time, the reaction mixture is poured into 1 liter of aqueous 3N sodium hydroxide. The mixture is then diluted to a volume of about 1700 mL with distilled water. A solid precipitate is collected by filtration and dried under reduced pressure, yielding 2-amino-3-cyano-5-bromo-6-methylpyrazine.

Quelle