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11th June 2015 @ 23:05

Reaction performed by Jason Chami, Evan Hockings, James Manton-Hall, Andreas Orsmond, Mac Shaw, James Kalas

SGS 5-2 (3.017 g, 12.91 mmol) was dissolved into DCM (150 mL) and stirred with PIDA (4.133 g, 12.83 mmol) overnight.

 

 

The reaction was stopped and the organic layer washed with saturated NaHCO3 solution (100 mL). The inorganic layer was extracted with CH2Cl2, (2 x 150 mL). The combined organic layers were filtered and the solvent removed by rotary evaaporation before the crude product was dried in vacuo.

 

Smiles: ClC1=CN=CC2=NN=C(C3=CC=NC=C3)N21

InChI=1S/C10H6ClN5/c11-8-5-13-6-9-14-15-10(16(8)9)7-1-3-12-4-2-7/h1-6H

4th June 2015 @ 23:31

Reaction performed by Jason Chami, Evan Hockings, James Manton-Hall, Andreas Orsmond, Alex Su, Mac Shaw and James Kalas

SGS 1-3 (crude, 9.15g, 6.33 mmol) was stirred into MeCN (120 mL) along with 2-pyridinecarboxaldehyde (6.787 g, 6.34 mmol). The mixture (a green suspension) was stirred for 72 hr at room temperature.

 

 

11.724 g of crude was produced

 

InChI=1S/C10H8ClN5/c11-9-6-13-7-10(15-9)16-14-5-8-2-1-3-12-4-8/h1-7H,(H,15,16)/b14-5+

SMILES ClC1=CN=CC(N([H])/N=C/C2=CN=CC=C2)=N1

 

 

1st June 2015 @ 23:01

Reaction performed by James Manton-Hall, Alex Su, Evan Hockings and James Kalas

SGS 1-3 (crude, 4.1g, 2.84 mmol) was stirred into MeCN (50 mL) along with 4-formylbenzonitrile (3.737 g, 2.85 mmol). The mixture (a light brown suspension) was stirred for 72 hr at room temperature.

 

InChI=1S/C12H8ClN5/c13-11-7-15-8-12(17-11)18-16-6-10-3-1-9(5-14)2-4-10/h1-4,6-8H,(H,17,18)/b16-6+

SMILES ClC1=CN=CC(N([H])/N=C/C2=CC=C(C#N)C=C2)=N1


 




28th May 2015 @ 22:41

Synthesis performed by Evan Hockings, James Manton-Hall, Andreas Orsmond, Jason Chami and James Kalas

SGS 1-3 (crude, 3.02 g, 21 mmol) was stirred into MeCN (36 mL). 4-Pyridinecarboxaldehyde (2.25 g, 21 mmol, density 1.137 g/mL) was added and the reaction mixture (terracotta) was stirred at room temperature for 72 h.  Solvent was removed in vaccuo to produce a pale orange solid.

3.82g of crude was produced

 

InChi:

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

and

InChI=1S/C6H5NO/c8-5-6-2-1-3-7-4-6/h1-5H

to

InChI=1S/C10H8ClN5/c11-9-6-13-7-10(15-9)16-14-5-8-2-1-3-12-4-8/h1-7H,(H,15,16)/b14-5+


Smiles

ClC1=CN=CC(NN)=N1

and

O=C([H])C1=CC=CN=C1

to

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

4th May 2015 @ 22:31
Reaction performed by Jason Chami, Alex Su, Evan Hockings, James Kalas

 

 

2,6-dichloropyrazine (40.7 g, 270 mmol) was dissolved in 100 mL EtOH and hydrazine hydrate (27.8 mL, 540 mmol) was added. The mixture was stirred under reflux for 7 h.  At this time tlc (DCM) showed the presence of a new material (Rf =0.21).  The cooled, crude mixture was allowed to stand overnight.

The solvent was then removed from the crude mixture in vacuo, giving an orange mixture of oil and solid to which EtOAc (200mL) and  water (150mL) was added. The aqueous layer was removed and washed with EtOAc (3x 100mL). The combined organic layers were concentrated in vacuo to produce an orange crystalline solid. 

11.84 g of crude was produced.