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5252120Attempts to the Bronstedt-acid catalysed Pictet-Spengler cyclization using N,N’-bis[3,5-bis(trifluoromethyl)phenyl]thiourea (MW44)
Experiments
profiles.google.com-micha.wolfleMichael Wolfle MeSO3H was added (5.2 µL of a 5% solution in CDCl3, 384 µg, 4.0 µmol, 5 mol%) After 4 h at r.t. no conversion was monitored -> heated to 60°C Comparison of the Reaction NMRs [data=text]352[/data] [data=text]354[/data] [data=text]356[/data] [data=text]358[/data] [b]Results:[/b] No conversion of the starting material was observed]]>MW43-1 as pretest for chiral derivatives of the catalyst - NMR-monitored experiments

Reaction Scheme


Table1


Hazard and Risk Assessment:
Reaction Class: 2
Hazards: T Toxic, X Irritant, C Corrosive
Risk rating: U = Unlikely

Start time: 4:30 PM 15/07/2010
End time: 10:30 PM 16/07/2010

General Procedure:
Each of the compound MW7, MW29-4, MW14, MW40-1 (75.0 µmol) shown in Table1 was solved in CDCl3 (~0.5 mL) in a NMR tube and MW43-1 (3.8 mg, 8.0 µmol, 10 mol%) was added and heated to 60°C for 18h.

MW44-1 – MW44-4: no conversion was monitored (by 1H NMR)

-> MeSO3H was added (5.2 µL of a 5% solution in CDCl3, 384 µg, 4.0 µmol, 5 mol%)
After 4 h at r.t. no conversion was monitored -> heated to 60°C

Comparison of the Reaction NMRs
Data: 1H NMR comparison MW44-1
Data: 1H NMR comparison MW44-2
Data: 1H NMR comparison MW44-3
Data: 1H NMR comparison MW44-4

Results:
No conversion of the starting material was observed
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]]>2010-07-15T06:05:27+01:002011-05-26T05:13:35+01:0066a2bc0219b7d7a5d85f9e333ac934bbehttps://www.ourexperiment.org/data/346.xmlhttps://www.ourexperiment.org/data/348.xmlhttps://www.ourexperiment.org/data/352.xmlhttps://www.ourexperiment.org/data/354.xmlhttps://www.ourexperiment.org/data/356.xmlhttps://www.ourexperiment.org/data/358.xmlhttp://www.ourexperiment.org/uri/4bhttps://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.htmlhttps://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.htmlhttps://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xmlhttps://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.pnghttps://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=525https://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=526https://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=527https://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=528https://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=529https://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=530https://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=531https://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=532https://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=533https://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=534https://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=535https://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=536https://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=541https://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=542https://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=543https://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=544https://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=545https://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=2120https://www.ourexperiment.org/racemic_pzq/525/Attempts_to_the_Bronstedtacid_catalysed_PictetSpengler_cyclization_using_NNbis35bistrifluoromethylphenylthiourea_MW44.xml?revision=6960
5256960Attempts to the Bronstedt-acid catalysed Pictet-Spengler cyclization using N,N’-bis[3,5-bis(trifluoromethyl)phenyl]thiourea (MW44)
Experiments
profiles.google.com-micha.wolfleMichael Wolfle MeSO3H was added (5.2 µL of a 5% solution in CDCl3, 384 µg, 4.0 µmol, 5 mol%) After 4 h at r.t. no conversion was monitored -> heated to 60°C Comparison of the Reaction NMRs [data=text]352[/data] [data=text]354[/data] [data=text]356[/data] [data=text]358[/data] [b]Results:[/b] No conversion of the starting material was observed]]>MW43-1 as pretest for chiral derivatives of the catalyst - NMR-monitored experiments

Reaction Scheme


Table1


Hazard and Risk Assessment:
Reaction Class: 2
Hazards: T Toxic, X Irritant, C Corrosive
Risk rating: U = Unlikely

Start time: 4:30 PM 15/07/2010
End time: 10:30 PM 16/07/2010

General Procedure:
Each of the compound MW7, MW29-4, MW14, MW40-1 (75.0 µmol) shown in Table1 was solved in CDCl3 (~0.5 mL) in a NMR tube and MW43-1 (3.8 mg, 8.0 µmol, 10 mol%) was added and heated to 60°C for 18h.

MW44-1 – MW44-4: no conversion was monitored (by 1H NMR)

-> MeSO3H was added (5.2 µL of a 5% solution in CDCl3, 384 µg, 4.0 µmol, 5 mol%)
After 4 h at r.t. no conversion was monitored -> heated to 60°C

Comparison of the Reaction NMRs
Data: 1H NMR comparison MW44-1
Data: 1H NMR comparison MW44-2
Data: 1H NMR comparison MW44-3
Data: 1H NMR comparison MW44-4

Results:
No conversion of the starting material was observed
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