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3rd March 2011 @ 07:44
Racemization experiments on enantioenrichend S-(+)-PZQamine (MW49-13) with ABCN as a radical initiator and thiophenol radical as an H abstractor.


See also:
Racemization of S-(+)-PZQamine with Raney Nickel (MW50-6, MW50-7)
Racemization of S-(+)-PZQamine with Pd/BaSO4 (MW50-5)
Racemization of S-(+)-PZQamine with Pd/C (MW50-4)
Racemization of S-(+)-PZQamine with Pd/C (MW50-1 to MW50-3)

Hazard and Risk Assessment:
HRAF MW50-8.pdf

Start time: 10:30 AM 4/03/2011
End time: 17:00 PM 4/03/2011

To a solution of S-(+)-PZQamine (50 mg, 247 µmol, MW: 202.3 g/mol) and thiophenol (5.4 mg, 5.0 µL, 49.4 mmol, 0.2 eq., d: 1.077 g/mL, MW: 110.2 g/mol) in benzene (5 mL) was at reflux for XX h in the precence of 1,1′-Azobis(cyclohexanecarbonitrile) (ABCN) (12.1 mg, 49.4 µmol, 0.2 eq. MW: 244.3 g/mol), which was divided in three equal portions and added successively every 2 h.

Work-up: solvents evaporated, dissolved in 1 N HCl, extracted with ethyl acetate, basified with Na2CO3 solution, extracted with ethyl acetate, dried over Na2SO4, evaporated

Crude Yield 32 g red solid.

[1] Thiyl Radical Mediated Racemization of Benzylic Amines, S. Escoubet, S. Gastaldi, N. Vanthuyne, G. Gil, D. Siri and M. P. Bertrand, Eur. J Org. Chem. 2006, 3242-3250. DOI: 10.1002/ejoc.200600120
Attached Files
HRAF MW50-8.pdf