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7th December 2016 @ 19:43
New: 1

CC1=NC(C)=C(Cl)[N+]([O-])=C1

ImageIMG_9860.JPG

SM/P 

2-chloro-3,5-dimethylpyrazine 

sulfuric acid, conc. 

potassium persulfate 

2-chloro-3,5-dimethylpyrazine 1-oxide 

mw 

142.59 

  

270.31 

158.59 

Equiv 

1.00 

  

1.07 

1.00 

mmol 

14.00 

  

15.00 

14.00 

mg 

2000 

  

4000 

2220 

mL 

  

14.00 

  

  

11/8/2016.  To a 1-neck 14/20 50 mL RB were added 14 mL of concentrated H2SO4, which was cooled to approximately 0 C with ice bath.  The pyrazine was then added, followed by potassium persulfate.  The resulting suspension was allowed to stir with warming to room temperature overnight. 

11/9/16.  The resulting clear solution was poured into a separatory funnel with distilled water and ice and extracted 3 x ~ 90 mL CHCl3.  The combined organic layer was washed with saturated aqueous NaHCO3, water, and brine and dried over MgSO4

11/13/16.  The resulting clear, colorless solution was concentrated with rotary evaporation to afford 2.5 g of a clear, colorless liquid from which a colorless solid formed upon cooling. 

11/14/16.  The Round bottom flask was placed under high vacuum for approximately 1-1.5 hours to afford 1.9 g of a colorless crystalline solid after removal of high vacuum volatiles.  

Crude yield 1900/2200 x 100 = 86%