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21st September 2016 @ 00:13

Scheme:

Outlined in [AEW 85-5]

Procedure:

1.011 g (6.75 mmol, 1eq) 2,6-dichloropyrazine was dissolved in 16 mL ethanol and 0.676 mL (10.8 mmol, 1.6 eq) hydrazine hydrate was added. The reaction mixture was stired under argon at reflux (80°C, 8h). The solution turned yellow.

Workup (9-8):

Solvent was removed on the rotary evaporator and the crude product was disolved in a mixture of water (15 mL) and ethyl acetate (15 mL). The organic layer was removed and the aqueous layer was extracted with EtOAc (3x10 mL). The organic layers were combined, washed with brine (10 mL), and dried with Na2SO4. Solvent was again removed on the rotary evaporator and the product was then placed on the high vacuum overnight. The reaction produced 0.775 g product (5.38 mmol, 80%).

NMR:

A sample of the product was disolved in CDCl3 and a 1H spectrum was recorded. This NMR is not consistent with the product produced in [AEW 85-5].

InChI:

InChI=1S/C4H2Cl2N2/c5-3-1-7-2-4(6)8-3/h1-2H

to

InChI=1S/C4H5ClN4/c5-3-1-7-2-4(8-3)9-6/h1-2H,6H2,(H,8,9)

Attached Files
rxn1product_PROTON_cdcl3.pdf
rxn1product_PROTON_cdcl3_01.jcamp