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14th July 2016 @ 02:33

Procedure

2,6-dichloropyrazine (21 g, 141 mmol, 1 eq) was dissolved in EtOH (282 mL, 0.50 M), and hydrazine hydrate (13.5 mL, 270 mmol, 2 eq) added. The reaction mixture was stirred at reflux for 16 hours.

The solvent was removed under reduced pressure to give a pale yellow solid. Water (~200 mL) and EtOAc (~300 mL) were added, and the mixture was shaken in an attempt to dissolve all solid. The organic layer was removed, the aqueous layer extracted with EtOAc (3 x 150 mL), and the combined organic layers washed with brine (~30 mL) before being concentrated under reduced pressure to yield a yellow solid (18.1, 125 mmol 89% yield.

HIRAC

HM 2-1.docx

 

Log

18th Jul

The reactant mixture apeared to be a  pale yellow turbid liquid.

As temperature went up, the mixture gradually turned clear and some precipitant formed. 

Temperature reached 70℃ at 16:30.

19th Jul

The temperature was about 80℃ at 10:00am and the reaction was monitered by TLC(100%Ethyl acetate), which showed the dichoropyrazine was almost completely consumed. 

Desired product is yellow solid(19.56g,yield 96%) NMR is clean and chemical shift of the sample (dissolved in CD3Cl) is the same as that of Alice's(see Synthesis of 2-Chloro-6-hydrazinylpyrazine (AEW 85-7))  though the integration seems a bit strange owing to fast exchange of N-H.

NMR DATA

HM2-1 DMSO.zip
HM2-1 CD3Cl.zip
HM2-1 DMSO.png
HM2-1 CD3Cl.png
Attached Files
HM New(2-1).png
HM 2-1.docx
IMG_2052.JPG
IMG_2056.JPG
TLC.jpg
HM2-1 DMSO.png
HM2-1 CD3Cl.png
HM2-1 DMSO.zip
HM2-1 CD3Cl.zip