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10th December 2014 @ 05:39
Resynthesis of SGS 1-1. Reaction performed by Trent Wallis. 2,6-dichloropyrazine (20 g, 134 mmol) was suspended in 100 mL EtOH and hydrazine hydrate (14.5 mL, 270 mmol) added. The mixture was stirred under reflux overnight.   Photos: 20 s after hydrazine addition [data]14273[/data]  30 min after hydrazine addition [data]14275[/data] 55 min after hydrazine addition [data]14277[/data] 17.5 hours after hydrazine addition [data]14295[/data] The ethanol was then removed from the crude mixture in vacuo at 60°C, giving an orange oil to which EtOAc (200mL) and  water (150mL) was added. The aqueous layer was removed and washed with EtOAc (3x 100mL). The combined EtOAc layers were concentrated in vacuo at 60°C to produce an orange oil that solidified upon slight cooling.  The crude product was recrystallised from ethanol/water; 6.865 g of a crystalline orange solid were obtained. Photos: Product mixture after removing the ethanol [data]14297[/data] Crude product after water wash, extraction into EtOAc and removal of EtOAc [data]14301[/data] No, Mr Hydrazine, I expect you to die! [data]14299[/data] Recrystallised product. [data]14319[/data] TLC (3:7 EtOAc:hexane) revealed a new spot at Rf = 0.68, SM at Rf = 0.85). [data]14321[/data] S = starting material, P = recrystallised product, Co = both S and P co-spotted. Conclusion: Looks like some starting material is still present... SMILES ClC1=CN=CC(Cl)=N1 to ClC1=CN=CC(NN)=N1 InChI InChI=1S/C4H2Cl2N2/c5-3-1-7-2-4(6)8-3/h1-2H to InChI=1S/C4H5ClN4/c5-3-1-7-2-4(8-3)9-6/h1-2H,6H2,(H,8,9)
Attached Files
SGS-1-2-start.jpg
SGS-1-2-30min.jpg
SGS-1-2-55min.jpg
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