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22nd August 2013 @ 10:29

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Reaction information

*#Reaction file  
CSRxnsScheme_115a.cdx
*Reaction file type CDX
*Procedure Dry pyridine (2.1 mL, 26.0 mmol) was added dropwise to 2‑(Pent-1-yn-1-yl)aniline (2.08 g, 13.0 mmol) in dry DCM (100 mL) at 0 °C.  Tosyl chloride (3.05 g, 16 mmol) was added at 0 °C.  The reaction mixture was stirred for 30 mins at 0 °C and at room temperature overnight.  The reaction mixture was poured into water (100 mL) and extracted with ether (3 × 50 mL).  The organic extracts were combined, washed sequentially with water (100 mL) and brine (100 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product as an orange solid (4.95 g).  Purification by column chromatography (SiO2, hexane/Et2O 9:1) gave the title compound as a pale yellow solid (3.52 g, 86%). 
*Yield (%)  86
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp90.pdf
AH Thesis_2011_pp176-223.pdf
Further information Compound 115a: 4-Methyl-N-(2-(pent-1-yn-1-yl)phenyl)benzenesulfonamide

For multistep reactions (or their steps):

Overall reaction? True
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For step in multistep reaction - link to previous reaction step  
For step in multistep reaction - link to following reaction step  
Attached Files
AH Thesis_2011_pp90.pdf
CSRxnsScheme_115a.cdx
AH Thesis_2011_pp176-223.pdf