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17th April 2013 @ 04:13

Formation of arryl pyrrole sulfonate salt to be chlorinated later on to produce a sulfonamide.

Reaction start time: 12:30 PM EST 13/4/13

MD 22-2 (3.0 g, 15 mmol, 1 equiv. ) and Sulfur trioxide pyridine (2.6 g, 15 mmol, 1 equiv.) were refluxed in toluene (15 mL) for 16 hours.

Reaction was concentrated under reduced atmosphere followed by addition of water and heated to 100° C, the boiling reaction was then neutralised with sodium carbonate (approx. 3 g). Water was removed under reduced pressure. A 90:10 ethanol:water mix (30 mL) was added to the residue and the solution heated to 90° C then filtered. The the dark brown solid was then concentrated  (2.1 g).

NMR showed the presence of only one methyl peak indicating a symmetrical product thus the desired product was not formed:

 

NMR:

MD_6-7_DMSO.pdf

 

Risk assessment and safety:

Same as: Synthesis of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate (MD 6-1)

Attached Files
MD_6-7_DMSO.pdf