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16th June 2017 @ 17:42

Lab notebook and NMR and GC/MS files attached. The product is similar to the NMR of the starting material as observed in [Rxn 3-3]  

(Images in lab notebook were reduced for uploading purposes.)

Attached Files
16th June 2017 @ 16:47

Lab notebook and relevent NMR and GC/MS attached. 10.3% Yield.

(Images in lab notebook had to be reduced for uploading purposes.)

 

Attached Files
10th December 2016 @ 03:49
Ringclosing: RingClosing

ClC1=CN=CC2=NN=C(N21)C3=CC=C(C=C3)OC(F)F

 

Attached is the NMR data after chroming. 

Attached Files
12th November 2016 @ 02:17

ClC1=CN=C(C)C2=NN=C(C3=CC=C(OC(F)F)C=C3)N21

Procedure was done on November 9th. It is being recorded now because OSM was done on that day. 

The reaction was quenched with the addition of saturated aqueous sodium hydrogen carbonate (250mL) and diluted with DCM (80mL). Orange layers were separated and aqueous layers were washed with DMC (3x100mL). The organic layers were washed with a saturate aqueous solution of sodium hydrogen carbonate (200 mL), brine (200mL), dried (MgSO4). DMC was evaporated using a rotovap to give a brown/orange sludge. 

Diethyl Ether (120 mL) was added to the brown/orange slude, and was dissolved upon stirring. TLC run on the compound. We were unsure of whether the starting material was either in the light or dark solution snapcap vials above the TLC plates in the pictures. Our plan is to separate the impurities via column chromotography. 

TLC Left: 

R=Light solution

C=Co-spot

P=Unknown Product.

Rf:0.26,0.80//Plate:Silica//Active under:UV//Solvent Hexane/EtOAc: 50/50

TLC Right:

R=Dark solution

C=Co-spot

P=Unknown Product.

Rf:0.74//Plate:Silica//Active under:UV//Solvent Hexane/EtOAc: 50/50

Attached Files
2nd November 2016 @ 20:16

ClC1=CN=C(C)C2=NN=C(C3=CC=C(OC(F)F)C=C3)N21

Solid product from step #2 (8.98g, 30mmol) , (E)-3-chloro-5-(2-(4-(difluoromethoxy)benzylidene)hydrazineyl)-2-methylpyrazine, was combined with CH2Cl2 (300ml) while stirring in a round bottom flask. PhI(OAC)2 (9.68g, 15.9 mmol) was then added. The solution was orange and the product was slowly dissolving. Although the reaction was only supposed to run over night, it was run for 5 days. At the end of the 5 days it was a translucent orange. 

Reference: http://malaria.ourexperiment.org/triazolopyrazine_se/14086/Synthesis_of_5chloro34difluoromethoxyphenyl124triazolo43apyrazine_AEW_2056.html 
 
11/3/16
TLC was taken of the orange product above and compared to the product from step #2. As shown in the picture.
S=Starting, Rf: 0.58,0.69,0.83.
C=Co-Spot
P=Product, Rf: 0.21,0.67,0.81
Active under: UV
Solvent Hexane/EtOAc: 50/50
Attached Files