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26th March 2014 @ 00:04

Conclusions: The reaction was successful with a 44% yield of the pure product. This is comparable to JU 3-6 with a 43% yield.

Resynthesis of JU 3-6

Github Tag: Issue #158

Reaction Scheme

Procedure

Started 11:40am

JU 2-2 (1.005 g, 3.88 mmol) was stirred into CH2Cl2 (60 mL). PhI(OAc)2 (1.255 g, 3.88 mmol) was added and the resulting solution was stirred at room temperature for 5.5 h. Analysis by TLC showed the reaction was incomplete.

TLC JU 3-7 EtOAc:Hexane 50:50 5.5 h.jpg

The reaction was stirred for a further 16.5 h. Analysis by TLC showed the reaction was incomplete.

TLC JU 3-7 EtOAc:Hexane 50:50 22 h.jpg

The reaction was stirred for a further 8 h. Analysis by TLC showed the reaction was incomplete.

TLC JU 3-7 EtOAc:Hexane 50:50 30 h.jpg

The reaction was stirred for a further 16 h. Analysis by TLC showed the reaction was incomplete. The reaction was stopped and worked up because it couldn;t be left over the weekend.

TLC JU 3-7 EtOAc:Hexane 50:50 46 h.jpg

The reaction mixture  was washed with 120 mL of saturated sodium hydrogen carbonate solution. The NaHCO3 layer was extracted with DCM (6 x 120 mL), dried over MgSO4 and filtered. The solvent was removed by rotary evaporation and dried in vacuo. The crude product was purified by flash column chromatography over silica. The column was first eluted with 50:50 EtOAc and Pet Benzine followed by 70:30 EtOAc:PB, and 100% EtOAC. The pure product was a pale yellow solid (437 mg, 44% yield) and was analysed by 1H NMR as were the impure fractions.

1H NMR, pure, DMSO, 200 MHz

JU 3-7 pure DMSO 200 MHz.pdf
JU 3-7 pure DMSO.zip

1H NMR, frac 10-96, DMSO, 200 MHz

This sample looks to be the starting material plus something else.

JU 3-7 frac 10-96 DMSO 200 MHz.pdf
JU 3-7 frac 10-96 DMSO.zip

 

HIRAC - see JU 3-1

InChI strings

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+

to

InChI=1S/C12H6ClN5/c13-10-6-15-7-11-16-17-12(18(10)11)9-3-1-8(5-14)2-4-9/h1-4,6-7H

SMILES

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

to

ClC1=CN=CC2=NN=C(C3=CC=C(C#N)C=C3)N21


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Attached Files
Reaction Scheme JU 3-1.png
TLC JU 3-7 EtOAc:Hexane 50:50 5.5 h.jpg
TLC JU 3-7 EtOAc:Hexane 50:50 22 h.jpg
TLC JU 3-7 EtOAc:Hexane 50:50 30 h.jpg
TLC JU 3-7 EtOAc:Hexane 50:50 46 h.jpg
JU 3-7 pure DMSO 200 MHz.pdf
JU 3-7 pure DMSO.zip
JU 3-7 frac 10-96 DMSO 200 MHz.pdf
JU 3-7 frac 10-96 DMSO.zip