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8th April 2014 @ 01:32

Repeat of JU 1-4 for synthesis of key starting material.

Reaction Scheme

Procedure

Started 5:30pm

2,6-Dichloropyrazine (Aldrich, 5.000 g, 33.6 mmol) was dissolved in ethanol (50 mL) to give a clear solution. Hydrazine hydrate (1.75 mL, 1.7 g, 34 mmol) was added dropwise resulting in a pale yellow solution. The resulting mixture was heated at reflux (bath temperature 80˚C) for 16 h. Analysis by TLC showed the reaction was complete and also that another product had appeared.

TLC JU 1-5 30:70 EtOAc:Hex 16 h.jpg

The solvent was removed by rotary evaporation and the crude product dried in vacuo. The crude product (5.02 g, 103% yield, 92% if product is a hydrate) was analysed by 1H NMR.

1H NMR, crude, DMSO, 200 MHz

JU 1-5 crude DMSO 200 MHz.pdf
JU 1-5 crude DMSO.zip
 


HIRAC & Risk Assessment

See JU 1-1

InChI strings

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)

SMILES

ClC1=CN=CC(Cl)=N1

to

ClC1=CN=CC(NN)=N1


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Attached Files
Reaction Scheme JU 1-3.png
TLC JU 1-5 30:70 EtOAc:Hex 16 h.jpg
JU 1-5 crude DMSO 200 MHz.pdf
JU 1-5 crude DMSO.zip
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