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18th April 2011 @ 05:51
Experiments on the oxidation of [url=http://www.ourexperiment.org/enantio_hydgen/1949][i]N[/i]-benzoyl-PZQ[/url] to the enamide by molten sulfur. See related experiments on rac-PZQ: [url=http://www.thesynapticleap.org/node/291]Sulfur melt data smogasbord[/url] [data=size:500x180]1067[/data] [b]Hazard and Risk Assessment:[/b] [data]1043[/data] Start time: 5:15 PM 18/04/2011 [b]MW59-1:[/b] [url=http://www.ourexperiment.org/enantio_hydgen/1949][i]N[/i]-benzoyl-PZQ[/url] (40 mg, 131 µmol, M.W. 306.4 g/mol) and sulfur (8.4 mg, 262 µmol, 2 eq., M.W. 32.1 g/mol) were heated at 180°C for 5 min. [b]MW59-2:[/b] [url=http://www.ourexperiment.org/enantio_hydgen/1949][i]N[/i]-benzoyl-PZQ[/url] (40 mg, 131 µmol, M.W. 306.4 g/mol) and sulfur (8.4 mg, 262 µmol, 2 eq., M.W. 32.1 g/mol) were heated at 180°C for 15 min. [b]MW59-3:[/b] [url=http://www.ourexperiment.org/enantio_hydgen/1949][i]N[/i]-benzoyl-PZQ[/url] (40 mg, 131 µmol, M.W. 306.4 g/mol) and sulfur (8.4 mg, 262 µmol, 2 eq., M.W. 32.1 g/mol) were heated at 180°C for 30 min. [b]MW59-4:[/b] [url=http://www.ourexperiment.org/enantio_hydgen/1949][i]N[/i]-benzoyl-PZQ[/url] (40 mg, 131 µmol, M.W. 306.4 g/mol) and sulfur (16.8 mg, 524 µmol, 4 eq., M.W. 32.1 g/mol) were heated at 180°C for 5 min. [b]MW59-5:[/b] [url=http://www.ourexperiment.org/enantio_hydgen/1949][i]N[/i]-benzoyl-PZQ[/url] (40 mg, 131 µmol, M.W. 306.4 g/mol) and sulfur (16.8 mg, 524 µmol, 4 eq., M.W. 32.1 g/mol) were heated at 180°C for 15 min. [b]MW59-6:[/b] [url=http://www.ourexperiment.org/enantio_hydgen/1949][i]N[/i]-benzoyl-PZQ[/url] (40 mg, 131 µmol, M.W. 306.4 g/mol) and sulfur (16.8 mg, 524 µmol, 4 eq., M.W. 32.1 g/mol) were heated at 180°C for 30 min. TLC (ethyl acetate, stain: ninhydrin, Ceric ammonium molybdate, Ceric ammonium molybdate, KMnO4) [data]1081[/data][data]1083[/data] [b]Results:[/b] All experiments showed left-over starting material -> reaction time has to be extended, see related reactions: [*] [url=http://www.ourexperiment.org/enantio_hydgen/1993]Scale-up: Oxidation of N-benzoyl-PZQ by sulfur (MW59-7)[/url] [*] [url=http://www.ourexperiment.org/enantio_hydgen/2052]Repetition: Oxidation of N-benzoyl-PZQ by sulfur (MW59-8)[/url] [b]References:[/b] [url=http://onlinelibrary.wiley.com/doi/10.1002/ardp.19893221104/abstract][1] Spectral and Chemical Properties of Pyrazino-[2,1-a]-isoquinolin-4-one Derivatives, K. Kiec'-Kononowicz, [i]Arch. Pharm.[/i] [b]1989[/b], [i]322[/i],795-799. DOI: 10.1002/ardp.19893221104.[/url]
Attached Files
Scheme MW59.png
TLC MW59.jpg
TLC MW59a.jpg