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31st March 2014 @ 08:07

Conclusion: The reaction was successful with an 88% crude yield if the product is a hydrate. The product was used in JU 2-3 without purification.

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

Reaction Scheme

Procedure

Started 7pm

2,6-Dichloropyrazine (Aldrich, 2.007 g, 13.4 mmol) was dissolved in ethanol (20 mL) to give a clear solution. Hydrazine hydrate (0.70 mL, 680 mg, 13.4 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.

TLC JU 1-4 30:70 EtOAc:Hex.jpg

The reaction was cooled to room temperature, the solvent was removed by rotary evaporation and the product dried in vacuo. The crude product (1.918 g, 99% yield, 88% if hydrate) was analysed by 1H NMR.

1H NMR, crude, DMSO, 200 MHz

JU 1-4 crude DMSO 200 MHz.pdf
JU 1-4 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 1-4 30:70 EtOAc:Hex.jpg
JU 1-4 crude DMSO 200 MHz.pdf
JU 1-4 crude DMSO.zip
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