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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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12th September 2016 @ 18:06

Continuing the work up from Nikishkin et al (2013)

First, upon entering the lab we noted that the product from our first attempt at step 1 was brick colored, instead of bright red, indicating that it is likely not the right compound, we will still do NMR on it, though. We set it aside in a vial for later.

 

Upon entering the lab, we saw our liquid from the reflux was opaque bright yellow. We added 15 mL of 1 M HCl and it immediaely turned bright red. We separated the aqueous and organic layers, collected the organic layer, and rotary evaporated off the volitiles to yield a nice bright red solid. We poured into the round bottom flask full of bright red solid 65 mL of diethyl ether and water each, as described in Nikishkin et al (2013). We swirled the flask around and observed a layer of red solid forming between the layers of water and ether. We purified this solid by vaccuum filtration and left it under high vacuum overnight. We expect that this solid is our desired compound [2], or 2-(6-chloropyrazin-2(1H)-ylidene)malononitrile. TLC and NMR will be performed soon

 

Citations

Nikishkin, Nicolai I. et al. "Pyrazine-Functionalized Calix[4]Arenes: Synthesis By Palladium-Catalyzed Cross-Coupling With Phosphorus Pronucleophiles And Metal Ion Extraction Properties". New J. Chem. 37.2 (2013): 391-402. Web. 4 Sept. 2016. .