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12th March 2014 @ 04:18

Conclusions: The reaction was successful with a 109% yield (probably >100% due to presence of water). The crude product was used in the synthesis of JU 2-2 without purifying.

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

Reaction Scheme

Procedure

Started 5pm

2,6-Dichloropyrazine (Aldrich, 1.00 g, 6.71 mmol) was dissolved in ethanol (10 mL) to give a clear solution. Hydrazine hydrate (0.35 mL, 360 mg, 7.2 mmol) was added dropwise resulting in a pale yellow solution. The resulting mixture was heated at reflux (bath temperature 80˚C) for 17 h. Examination of the reaction by TLC under UV light showed the reaction was complete (solvent system = 30/70 EtOAC/Hexane).

TLC JU 1-2 30:70 EtOAc:Hex.jpg

The sample was concentrated under reduced pressure and in vacuo to yield a pale orange solid (1.19 g) that was examined by 1H NMR spectroscopy. Crude yield of 122%, 109% if the product is a hydrate.

1H NMR, crude, DMSO, 200 MHz

JU 1-2 crude DMSO 200 MHz.pdf
JU 1-2 crude DMSO.zip

1H NMR, 2,6-dichloropyrazine, DMSO, 200 MHz

2,6-dichloropyrazine DMSO 200 MHz.pdf
2,6-dichloropyrazine 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 1-1.png
TLC JU 1-2 30:70 EtOAc:Hex.jpg
JU 1-2 crude DMSO 200 MHz.pdf
JU 1-2 crude DMSO.zip
2,6-dichloropyrazine DMSO 200 MHz.pdf
2,6-dichloropyrazine DMSO.zip
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