Sodium Hydroxide → HCID 15335269, compound

HRID 1734151Notes

Reaction equation

HRID 1734151 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[N:6][CH:5]=[C:4]([CH3:10])[N:3]=1.[Br:11]N1C(=O)CCC1=O.[OH-].[Na+]>CN(C)C=O.O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[N:6][C:5]([Br:11])=[C:4]([CH3:10])[N:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 12270162Pyrazinecarbonitrile, 3-amino-5-methyl-

Product 1

HCID 15335269HCID 15335269, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

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, 1299 (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.

Workup

  1. temperaturewhile maintaining the reaction mixture temperature at about 15°-25° C
  2. additionUpon completion of addition
  3. filtrationA solid precipitate is collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-6ce780528dca4dc4bd87307a05fca809
Source dataset
uspto-grants-1996_07
Patent number
US05532367

Reaction notes

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