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22nd August 2013 @ 10:32

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Reaction information

*#Reaction file  
CSRxnsScheme_125.cdx
*Reaction file type CDX
*Procedure  4-Methylbenzenesulfonamide (5.19 g, 30.0 mmol) and NaOH (2.42 g, 2.4 mmol) in DMSO (50 mL) were heated at 50 °C for 30 mins.  1-bromonon-4-yne (5.13 g, 25.0 mmol) was added and the reaction mixture stirred at 50 °C for a further 2 h.  The reaction mixture was poured into water (100 mL) and extracted with ether (3 × 50 mL).  The organic extracts were combined, washed with water (2 × 100 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product as a colourless oil (5.85 g).  Purification by column chromatography (SiO2, hexane) gave the title compound as a colourless oil (3.74 g, 50%).
*Yield (%)  50
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp95.pdf
AH Thesis_2011_pp176-223.pdf
Further information  Compound 125: 4-Methyl-N-(non-4-yn-1-yl)benzenesulfonamide

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
AH Thesis_2011_pp95.pdf
CSRxnsScheme_125.cdx
AH Thesis_2011_pp176-223.pdf