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6th September 2016 @ 18:18

 (performed on 9/6)

 first step of nemesis synthesis

 

compound

MW (g/mol)

mol (mmol) g           density (g/mL) volume (mL) equivalents
[2,6] dichloropyrazine 148.98 6.7 1     1
hydrazine hydrate 32.045 6.7 0.340   0.33 1
ethanol         10  
2-Chloro-6-hydrazinylpyrazine 144.56  6.7  0.969     1

 

[2,6]-Dichloropyrazine (1 g, 6.7 mmol) was stirred in ethanol (10 mL) and hydrazine hydrate (80% by volume, 0.41 mL). The mixture was refluxed at 80 ˚C (personal note: variac set at 20 V) under Ar for ~22 hours. 

(9/7)

The resulting mixture was vacuum filtered to yield a crude yellow solid (0.089 g). TLC seemed to indicate this material contained some unreacted starting material.

The remaining solvent was removed under reduced pressure to give an orange solid (0.6884 g, 4.76 mmol, 71% yield). This product was analyzed via TLC and NMR (attached).

The prepared NMR sample contained particulates, which could possibly explain some of the strange peaks in our spectrum. From here on out, we will be sure to filter our samples before running them through NMR.

TLC: silica plate, 30% EtOAc/Hexanes; SM-starting material, C-cospot, P-"product"

This is following Alice Williamson's procedure in entry AEW_851.

Linked Entries
Attached Files
MRLS proton nmr
TLC of vacuum filtered product
TLC of orange solid