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30th August 2013 @ 13:15

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Reaction information

*#Reaction file  
Scheme_393.cdx
*Reaction file type CDX
*Procedure To a stirred solution of 2-benzyl-5-butylidene-4-methylsulfanylmethylene-2,3,4,5-tetrahydro-1H-benzo[c]azepine (350 mg, 1.0 mmol) in diethyl ether (1.0 mL), N-phenylmaleimide (173 mg, 1.0 mmol) was added, refluxed for 12 hrs then quenched with a saturated solution of NaHCO3 (30.0 mL).  The product was extracted into diethyl ether (3 x 50 mL), the combined organic layer washed with water (4 x 50 mL), brine (50.0 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure.  Radial chromatography (SiO2, 0-100 % Et2O:petroleum followed by 2:1 ethyl acetate:diethyl ether including 5 % Et3N) afforded the title compound as a pale yellow oil (238 mg, 0.5 mmol, 45 %). 
*Yield (%)  45
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp139.pdf
Further information  

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Overall reaction? True
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Attached Files
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp139.pdf
Scheme_393.cdx