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09-06-2016, First step in synthesis of the hetero-oxadiazole, reaction of 2-6 dichloropyrazine with malononitrile, following procedure from Nikishkin et al (2013)
09-11-2016, Work up of the second attempt at step 1
09-23-2016. Step 1 redo, on 5 gram scale
09-24-2016. Work up of 09-23-2016
09-29-2016, work up and purification of [4]
09/28/2016 Step 4, on a larger scale this time. Conversion of methyl 6-chloropyrazine-2-carboxylate [3] to methyl 6-hydrazineylpyrazine-2-carboxylate [4] using hydrazine according to AEW 85-5
10/07/2016 GC mass spec characterization of rxn from [4]->[5]
10/18/16: Trial work up of reaction of 6-chloropyrazinecarbonitrile and hydrazine
10/4/16: Trial of Step 4:Product [4] to Product [5]
10/6/16: Trial Synthesis of 6-hydrazinelypyrazine-2-carbonitrile and from 6- hydrazinelypyrazine-2-carboximidhydrazide from chloropyrazinecarbonitrile
9/12/16 Step 2 in synthesis. Going from [2]->[3]
9/13/16: Work-up of product [3] and TLC plates
9/15/16: Second Synthesis of Methyl 6-chloropyrazine-2-carboxylate [product 3]
9/18/16-9/20/16: Trial Synthesis of Methyl 6-hydrazineylpyrazine-2-carboxylate (Product 4)
9/22/16: Inconclusive Trial Synthesis of Methyl 6-hydrazineylpyrazine-2-carboxylate (Product 4)
9/25/16-9/27/16: Synthesis of Product 3, methyl 6-chloropyrazine-2-carboxylate
9/27/2016 Late Night
9/29/2016 HNMR of product 4, and HNMR of product 4 after D2O exchange 01/10/2016
9/8/16-Continued Synthesis of 2-(6-chloropyrazin-2(1H)-ylidene)malononitrile
CNMR so far
HNMR so far, of all relevant compounds
The Synthetic scheme of Hetero-oxadiazole Synthesis
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20th October 2016 @ 20:10

CNMR data were taken along the way as we reacted, and are shown here.

 

CNMR of starting material [1] is taken in CDCl3, two peaks are seen and can be assigned to the aromatic carbons, one more downfield than the other due to a bond to Cl. There are two impurities

Screen Shot 2016-10-20 at 3.10.11 PM.png

CNMR of product [2], there were fewer peaks than expected, but we were able to find a peak D in the nitrile range, which indicates the proper product was made. In the future, a greater number of scans in the NMR protocol will be needed to resolve a better spectrum with a complete set of peaks. Due to incomplete set of peaks, accurate assignment of all peaks was not possible

Screen Shot 2016-10-20 at 3.10.22 PM.png

 

CNMR of product [3], excellent resolution, we are very excited that peaks E and F indicate successful synthesis of a methyl ester

Screen Shot 2016-10-20 at 3.10.29 PM.png

 

CNMR of product [4] had especially low resolution, but we were able to see peaks E and F again, indicating that the hydrazine reaction did not effect the methyl ester moiety as we had feared it might. We could not successfully identify all of the aromatic carbons, and this experiment needs to be repeted with more scans taken in the NMR protocol.

Screen Shot 2016-10-20 at 3.10.36 PM.png

 

Attached Files
Screen Shot 2016-10-20 at 3.10.22 PM.png
Screen Shot 2016-10-20 at 3.10.11 PM.png
Screen Shot 2016-10-20 at 3.10.29 PM.png
Screen Shot 2016-10-20 at 3.10.36 PM.png