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19622107Oxidation of N-benzoyl-PZQ by sulfur (MW59-1 to MW59-6)
Experiments
profiles.google.com-micha.wolfleMichael Wolfle 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]]]>N-benzoyl-PZQ to the enamide by molten sulfur.
See related experiments on rac-PZQ: Sulfur melt data smogasbord

Scheme MW59.png


Hazard and Risk Assessment:
HRAF MW57.pdf


Start time: 5:15 PM 18/04/2011

MW59-1:
N-benzoyl-PZQ (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.

MW59-2:
N-benzoyl-PZQ (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.

MW59-3:
N-benzoyl-PZQ (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.

MW59-4:
N-benzoyl-PZQ (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.

MW59-5:
N-benzoyl-PZQ (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.

MW59-6:
N-benzoyl-PZQ (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)
TLC MW59.jpg
TLC MW59a.jpg


Results:
All experiments showed left-over starting material -> reaction time has to be extended, see related reactions:
  • Scale-up: Oxidation of N-benzoyl-PZQ by sulfur (MW59-7)
  • Repetition: Oxidation of N-benzoyl-PZQ by sulfur (MW59-8)

    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.
    ]]>2011-04-18T05:51:36+00:002011-05-24T13:18:44+00:0017a23e292112c9b0e24ca2e93674c29968https://www.ourexperiment.org/data/1067.xmlhttps://www.ourexperiment.org/data/1081.xmlhttps://www.ourexperiment.org/data/1083.xmlhttp://www.ourexperiment.org/uri/123https://www.ourexperiment.org/enantio_hydgen/1962/Oxidation_of_NbenzoylPZQ_by_sulfur_MW591_to_MW596.htmlhttps://www.ourexperiment.org/enantio_hydgen/1962/Oxidation_of_NbenzoylPZQ_by_sulfur_MW591_to_MW596.htmlhttps://www.ourexperiment.org/enantio_hydgen/1962/Oxidation_of_NbenzoylPZQ_by_sulfur_MW591_to_MW596.xmlhttps://www.ourexperiment.org/enantio_hydgen/1962/Oxidation_of_NbenzoylPZQ_by_sulfur_MW591_to_MW596.pnghttps://www.ourexperiment.org/enantio_hydgen/1962/Oxidation_of_NbenzoylPZQ_by_sulfur_MW591_to_MW596.xml?revision=1962https://www.ourexperiment.org/enantio_hydgen/1962/Oxidation_of_NbenzoylPZQ_by_sulfur_MW591_to_MW596.xml?revision=1963https://www.ourexperiment.org/enantio_hydgen/1962/Oxidation_of_NbenzoylPZQ_by_sulfur_MW591_to_MW596.xml?revision=1964https://www.ourexperiment.org/enantio_hydgen/1962/Oxidation_of_NbenzoylPZQ_by_sulfur_MW591_to_MW596.xml?revision=1965https://www.ourexperiment.org/enantio_hydgen/1962/Oxidation_of_NbenzoylPZQ_by_sulfur_MW591_to_MW596.xml?revision=1969https://www.ourexperiment.org/enantio_hydgen/1962/Oxidation_of_NbenzoylPZQ_by_sulfur_MW591_to_MW596.xml?revision=1970https://www.ourexperiment.org/enantio_hydgen/1962/Oxidation_of_NbenzoylPZQ_by_sulfur_MW591_to_MW596.xml?revision=1971https://www.ourexperiment.org/enantio_hydgen/1962/Oxidation_of_NbenzoylPZQ_by_sulfur_MW591_to_MW596.xml?revision=1972https://www.ourexperiment.org/enantio_hydgen/1962/Oxidation_of_NbenzoylPZQ_by_sulfur_MW591_to_MW596.xml?revision=1992https://www.ourexperiment.org/enantio_hydgen/1962/Oxidation_of_NbenzoylPZQ_by_sulfur_MW591_to_MW596.xml?revision=2035https://www.ourexperiment.org/enantio_hydgen/1962/Oxidation_of_NbenzoylPZQ_by_sulfur_MW591_to_MW596.xml?revision=2107https://www.ourexperiment.org/enantio_hydgen/1962/Oxidation_of_NbenzoylPZQ_by_sulfur_MW591_to_MW596.xml?revision=7142
    19627142Oxidation of N-benzoyl-PZQ by sulfur (MW59-1 to MW59-6)
    Experiments
    profiles.google.com-micha.wolfleMichael Wolfle 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]]]>N-benzoyl-PZQ to the enamide by molten sulfur.
    See related experiments on rac-PZQ: Sulfur melt data smogasbord

    Scheme MW59.png


    Hazard and Risk Assessment:
    HRAF MW57.pdf


    Start time: 5:15 PM 18/04/2011

    MW59-1:
    N-benzoyl-PZQ (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.

    MW59-2:
    N-benzoyl-PZQ (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.

    MW59-3:
    N-benzoyl-PZQ (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.

    MW59-4:
    N-benzoyl-PZQ (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.

    MW59-5:
    N-benzoyl-PZQ (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.

    MW59-6:
    N-benzoyl-PZQ (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)
    TLC MW59.jpg
    TLC MW59a.jpg


    Results:
    All experiments showed left-over starting material -> reaction time has to be extended, see related reactions:
  • Scale-up: Oxidation of N-benzoyl-PZQ by sulfur (MW59-7)
  • Repetition: Oxidation of N-benzoyl-PZQ by sulfur (MW59-8)

    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.
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