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12th April 2011 @ 02:06
Experiments on the oxidation of PZQamine to the enamide/imine by molten sulfur.
See related experiments on rac-PZQ: Sulfur melt data smogasbord

Scheme MW57.png


Hazard and Risk Assessment:
HRAF MW57.pdf


Start time: 11:30 AM 12/04/2011

MW57-1:
rac-PZQamine (40 mg, 198 µmol, M.W. 202.3 g/mol) and sulfur (12.7 mg, 2 eq., M.W. 32.1 g/mol) were heated at 180°C for 5 min.

MW57-2:
rac-PZQamine (40 mg, 198 µmol, M.W. 202.3 g/mol) and sulfur (12.7 mg, 2 eq., M.W. 32.1 g/mol) were heated at 180°C for 10 min.
1H NMR MW57-2.pdf


MW57-3:
rac-PZQamine (40 mg, 198 µmol, M.W. 202.3 g/mol) and sulfur (12.7 mg, 2 eq., M.W. 32.1 g/mol) were heated at 180°C for 15 min.

TLC57-3.jpg
TLC57-3a.jpg
1H NMR MW57-3.pdf



Start time: 11:30 AM 12/04/2011

MW57-4:
rac-PZQamine (20 mg, 99 µmol, M.W. 202.3 g/mol) and sulfur (6.4 mg, 2 eq., M.W. 32.1 g/mol) were heated at 180°C for 30 min.

MW57-5:
rac-PZQamine (20 mg, 99 µmol, M.W. 202.3 g/mol) and sulfur (6.4 mg, 2 eq., M.W. 32.1 g/mol) were heated at 180°C for 1 h.

MW57-6:
rac-PZQamine (20 mg, 99 µmol, M.W. 202.3 g/mol) and sulfur (12.7 mg, 4 eq., M.W. 32.1 g/mol) were heated at 180°C for 15 min.

MW57-7:
rac-PZQamine (20 mg, 99 µmol, M.W. 202.3 g/mol) and sulfur (12.7 mg, 4 eq., M.W. 32.1 g/mol) were heated at 180°C for 30 min.


References:
[1] Spectral and Chemical Properties of Pyrazino-[2,1-a]-isoquinolin-4-one Derivatives, K. Kiec'-Kononowicz, Arch. Pharm. 1989, 322,795-799. DOI: 10.1002/ardp.19893221104.
Attached Files
Scheme MW57.png
HRAF MW57.pdf
1H NMR MW57-2.pdf
1H NMR MW57-3.pdf
TLC57-3.jpg
TLC57-3a.jpg
TLC57-3a.jpg