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11th August 2016 @ 06:05

Reference:PCT/US2008/012717

Procedure:

For details of synthesis of hydrazinylpyrazine, see Synthesis of 2-Chloro-6-hydrazinylpyrazine (AEW 85-7)

Hydrazinylpyrazine can also be purchased commercially.

Hydrazinylpyrazine (8.00g, 55.3mmol, 1 equiv.), triethyl orthoformate (16.40g 18.4 ml, 111 mmol, 2 equiv.)were dissolved in xylene (200ml) and heated at reflux with stiring for 2 hr. The mixture was brought to RT. Dithyl ether was added and the suspension was filtered. The solid was collected and washed with diethyl ether to afford the product 

Strings:

ClC1=CN=CC(NN)=N1

and

CCOC(OCC)([H])OCC

to

ClC1=CN=CC2=NN=CN21

InChI=1S/C4H5ClN4/c5-3-1-7-2-4(8-3)9-6/h1-2H,6H2,(H,8,9)  

and  

InChI=1S/C7H16O3/c1-4-8-7(9-5-2)10-6-3/h7H,4-6H2,1-3H3  

to  

InChI=1S/C5H3ClN4/c6-4-1-7-2-5-9-8-3-10(4)5/h1-3H

HIRAC

HM 1-4.docx

Log


11th Aug

The reation started at 16:00pm

The SM wouldn't dissolve in the xylene at first.

As the temperature became higher the mixture became darker and clearer then formed a clear dark red solution when the bath temperature was 100℃.

The reaction was left overnight.

12th Aug

TLC was performed  (75% of ethyl acetat in petroleum) at 10:00am. Only a little product was formed. 2% of tosylic acid was added.

TLC was performed at 1:20 pm the product spot looked thicker

15th Aug

After weekends, TLC still looked the same, the reaction was switched off at 10:00am anyway, no stick solid was formed. 100ml of diethyl ether was added, and the mixture was filtered to give about 2g of fine black powder. TLC showed there was almost no difference between the powder and the solution. The solution was concentrated. And brown solid was afforded. 

18th Aug

The solid was dissolved in ethyl acetate and silica gel was added. Manual column was perfomed to yield 2.4grams of pale yellow powder. NMR is perfect though yield is no good enough(More catalyst should have ben added. It could be an equilibrium)

 

NMR DATA

HM 1-4.png
HM 1-4.zip
Attached Files
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HM 1-4.docx
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HM 1-4.png
HM 1-4.zip
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