O-Toluidine → 1-(Phenylsulfonyl)-N-o-tolyl-3-(trifluoromethyl)-1H-pyrrole-2-carboxamide

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Reaction Steps

In a three-necked round-bottom flask o-toluidine (0.53 g, 5 mmol) was dissolved in 15 mL of toluene under inert atmosphere. To this solution was added trimethy aluminium (2.5 mL, 5 mmol) and the mixture was stirred at room temperature during 10 minutes. Afterwards, a solution of methyl 1-(phenylsulfonyl)-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate (207 mg, 0.62 mmol) in 15 mL of toluene were added and the reaction mixtures was heated at 80° C. over night. Next, the mixture was allowed to cool to room temperature and 2-3 mL of water were added to hydrolyze unreacted trimethyl aluminium and a 0,5M aqueous solution of disodium tartrate dihydrate were added stirring for a while. Afterwards, the two layers were separated and the aqueous phase was extracted with ethyl acetate. The organic mixture was washed with the same 0,5M aqueous solution of disodium tartrate dihydrate (25 mL), water and brine, dried and concentrated in vacuum to afford 560 mg of a residue that was used in the following step without further purification.

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