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8th October 2016 @ 03:56

 Following [AEW 205-6]

 

Reaction Scheme

 


Procedure

1.3101 g (4.386 mmol, 1 eq) of 2-Chloro-6-hydrazinylpyrazine, were dissolved in 25 mL DCM to form a dark-yellow suspension/sludge. Approximately 1.6 g (5.0 mmol, 1.1 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 25 mL saturated NaHCO3 solution, then transfered to a seperatory funnel. The organic layer was removed, and the aqueous layer was extracted with 20 mL DCM four times. The organic layers were combined, and washed with 20 mL saturated NaHCO3, then washed with 20 mL brine. Drying agent was added, and the solution was filtered. Solvent was removed via rotory evaporation and high vac. The product was then left to sit in an open flask in the hood for 1 week, over which the product changed from light brown to red-brown.The product was dissolved again in DCM, transfered to another round bottom flask, rotory evaporated and placed on the hi vac to give a yield of 1.1852 g (3.9951 mmol, 91.09% yield).


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_R3-2.pdf
HNMR_R3-2.jcamp
CNMR_R3-2_dmso.pdf
rxn3r2_CARBON_dmso.jcamp
Reaction 3-2 GCMS.pdf