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30th August 2013 @ 13:28

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Reaction information

*#Reaction file  
Scheme_402.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of 4-phenyl-4,5-dihydro-3H-1,2,4-triazole-3,5-dione (150 mg,  0.5 mmol), boron trifluoride diethyl ether complex (347 mg, 3.0 mmol) dissolved in dichloromethane (1.0 mL), at -78 °C, 4-[(E)Butylidene]-3-[(Z)-1-(methylthio)methylidene]-1-(phenylmethyl)perhydroazepine (396, 150 mg, 0.5 mmol) was added dropwise, warmed to room temperature, refluxed at 36 °C for 20 minutes.  The product extracted with diethyl ether (3 x 30 mL), the combined organic layer washed with water (3 x 30 ml) and brine (30.0 mL), dried MgSO4, filtered and the solvent removed under reduced pressure.  Radial chromatography (SiO2, 5-100% diethyl ether:ethyl acetate including 5 % Et3N) afforded the title compound as a viscous oil (35 mg, 0.075 mmol, 15 %).

*Yield (%)  15
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp147.pdf
DM Thesis_2000_pp51-59.pdf
Further information  

For multistep reactions (or their steps):

Overall reaction? True
For overall reaction - links to child reaction steps  
For step in multistep reaction - link to previous reaction step  
For step in multistep reaction - link to following reaction step  
Attached Files
Scheme_402.cdx
DM Thesis_2000_pp147.pdf
DM Thesis_2000_pp51-59.pdf