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8th October 2016 @ 03:10

Scheme:


Following [AEW 85-5]

Procedure:

Dichloropyrazine (2.000 g, 13.4 mmol, 1eq) was disolved in ethanol and stirred under argon. Hydrazine hydrate (80% w/w, 1.35 mL, 21.6 mmol, 1.6eq) was added dropwise. The reaction mixture was stirred at reflux under argon (80°C, 23h). The solution turned a transparent yellow.

Workup (9-13):

Solvent was removed on the rotary evaporator. The resulting solid was disolved in ethyl acetate (40 mL) and water (40 mL). The organic layer was removed and the aqueous layer was extracted with EtOAc (4 x 20 mL, 1 x 40 mL). The orgaic layers were combined and washed with brine (20 mL). They were then dried with MgSO4 and concentrated on the rotary evaporator and then dried on the high vacuum. The reaction yielded 1.66 g (11.5 mmol, 86% yield).

NMR:

A sample was disolved in CDCl3 and a 1H proton spectrum was recorded.

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
rxn1r2_prod_PROTON_cdcl3.pdf
Step 1 attempt 2 product TLC 9-13-16 v1.jpg
Step 1 attempt 2 product TLC 9-13-16 v2.jpg