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16th September 2016 @ 22:25

 Following [AEW 205-6]

 

Reaction Scheme

 


Procedure

0.4326 g (1.446 mmol, 1 eq) of 2-Chloro-6-hydrazinylpyrazine [rxn 1-1], were dissolved in 13 mL DCM to form a dark-yellow suspension/sludge. 0.5267 g (1.635 mmol, 1.129 eq) of PhI(OAc)2 were added, and the solution was stirred under inert atmosphere. As the reaction proceded, the solution cleared and became red-brown.

 

Workup

The reaction was quenched with 5 mL saturated NaHCO3 solution. The solution was diluted with 4 mL DCM, then transfered to a seperatory funnel. The organic layer was removed, and the aqueous layer was extracted with 10 mL DCM thrice. The organic layers were combined, and washed with 7 mL saturated NaHCO3, then washed with 7 mL brine. Drying agent was added, and the solution was filtered. Solvent was removed via rotory evaporation and high vac to yield 0.3699 g (1.247 mmol, 86.12% yield) product.


InChI

InChI=1S/C12H9ClF2N4O/c13-10-6-16-7-11(18-10)19-17-5-8-1-3-9(4-2-8)20-12(14)15/h1-7,12H,(H,18,19)/b17-5+

to 

InChI=1S/C12H7ClF2N4O/c13-9-5-16-6-10-17-18-11(19(9)10)7-1-3-8(4-2-7)20-12(14)15/h1-6,12H


SMILES

ClC1=CN=CC(N([H])/N=C/C2=CC=C(OC(F)F)C=C2)=N1

to
 
ClC1=CN=CC2=NN=C(C3=CC=C(OC(F)F)C=C3)N21
Attached Files
HNMR_R3-1.pdf
HNMR_R3-1.jcamp