All Notebooks | Help | Support | About
1st October 2016 @ 22:45

Scheme:


Following [AEW 85-5]

Procedure:

Dichloropyrazine (2.055 g, 13.8 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 (9-29):

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 1.75 g (12.1 mmol, 88%).

NMR:

A sample was disolved in DMSO and 1H and 13C spectra were recorded.

TLC (10/18):

A TLC plate was run in 1:1 EtOAc/Hexanes and visualized with UV. Streaking is expected of amines.

TLC Reaction 1-3 Annotated.jpg

GC/MS

A sample of the product was disolved in EtOAc and run on the GCMS. Results are consistant with the expected product.

rxn1r3_chrom.png
rxn1r3_MS.png

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
rxn1r3_PROTON_dmso.pdf
rxn1r3_CARBON_dmso.pdf
AMS_rxn1r3_PROTON_dmso_01.jcamp
TLC Reaction 1-3 Annotated.jpg
rxn1r3_chrom.png
rxn1r3_MS.png