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5th December 2016 @ 10:59

AT-1-023

Synthesis of (E)-2-chloro-6-(2-(4(pyrrolindin-1-yl)benzylidene)hydrazine)pyrazine (AT-1-023) from 4-(pyrrolindin-1-yl)benzaldehyde and 2-chloro-6-hydrazinylpyrazine in a condensation reaction

 reaction scheme

 

 

Reagent

Eq

Mw

mmol

w/vol

4-(pyrrolindin-1-yl)benzaldehyde

1

175.23

0.9823

172mg

2-chloro-6-hydrazinylpyrazine

1

144.56

0.9823

142mg

Ethanol

~

46.07

~

8ml

 

Experimental Procedure

 

2-chloro-6-hydrazinylpyrazine (0.142g, 0.9823mmol) and ethanol (8ml) were placed into a round bottom flask. 4-(pyrrolindin-1-yl)benzaldehyde (0.172g, 0.9823mmol) was also added to the round bottom flask. The reaction was stoppered and put on to mix for 2.5 hours.

IMG_2808.png

IMG_2811.png

During this time the colour of the reaction changed from orange to bright red.

TLC’s ( 1:1 pet ether/ EtOAc) had to go through a mini work up before TLC’s could be taken as the mixture was too concentrated and distorted the spots.

IMG_2826.png

The TLC showed the loss of the starting material from the product and the formation of what we assumed to be product. Once this was confirmed, the solvent was removed in vacuo and an NMR was taken. It showed some solvent impurities so the solution was washed in d-chloroform and the solvent was removed in vacuo  again.

The Final product was given as an red solid (0.2706g, 0.899mmol, 91%). 1H NMR showed that the product had been formed had some ethanol impurities, even after washing in d-chloroform. Apart from that the product seemed to be clean.

 

crude nmr at-23.png

final nmr at-23.png

at-23 cosy.png

Reference

  1. Open source malaria: our experiment, http://malaria.ourexperiment.org/triazolopyrazine_se/9268/Synthesis_of_E2chloro62naphthalen2ylmethylenehydrazinylpyrazine_TY_21.html, date accessed: 04/11/16

 

Attached Files
IMG_2808.png
IMG_2811.png
final nmr at-23.png
IMG_2826.png
crude nmr at-23.png
at-23 cosy.png
reaction with ethanol.png