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23rd September 2014 @ 03:17

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Reaction Scheme


Procedure

AEW 85 (3.0 g, 21 mmol) was stirred into a solution of AcOH (1.2 mL) and MeCN (66 mL). 4-(difluoromethoxy)benzaldehyde (2.7 mL, 3.6 g, 21 mmol) was added and the reaction mixture (yellow solution) was stirred at room temperature overnight (bright yellow suspension) containing brown solid that wouldn't go into solution when sonicated.

The suspension was decanted to leave the dark brown solid inside the flask and  a fluffy yellow solid was collected. Washed with cold MeCN and dried at high vac (3.29 g, 11.2 mmol, 53% yield), NMR showed pure product. The yellow filtrate was concentrated in vacuo to give a shiny yellow solid that looked like the product by TLC and comparison of the material (2.59 g, 8.67 mmol, 42% yield - needs NMR).

Data:

AEW 204-1 first filt 200 MHZ nmr.pdf
2014-09-25 15.47.59.jpg
 

Ref Data and 

Hazard and Risk Assessment:

 See  Synthesis of 2-chloro-6-(2-(4-(difluoromethoxy)benzylidene)hydrazinyl)pyrazine (JU 18-1)


InChI strings

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

and

InChI=1S/C8H6F2O2/c9-8(10)12-7-3-1-6(5-11)2-4-7/h1-5,8H

to

InChI=1S/C12H9ClF2N4O/c13-10-6-16-7-11(18-10)19-17-5-8-1-3-9(4-2-8)20-12(14)15/h1-7,12H,(H,18,19)/b17-5+


SMILES

ClC1=CN=CC(NN)=N1

and

[H]C(C1=CC=C(OC(F)F)C=C1)=O

to

ClC1=CN=CC(N/N=C/C2=CC=C(OC(F)F)C=C2)=N1

Attached Files
AEW 204-1 first filt 200 MHZ nmr.pdf
AEW 204-1yellow solid filt.zip
2014-09-25 15.47.59.jpg