Triethylamine → 1-Methyl-beta-oxo-alpha-(p-nitrophenylcarbamoyl)-2-pyrrolpropionitrile

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Reaction Steps

The solution of 4.9 g of the 1-methyl-β-oxo-2-pyrrolpropionitrile in 50 ml of toluene, 5 ml of dimethylsulfoxide and 4 g of triethylamine is treated with the solution of 5.7 g of p-nitrophenylisocyanate in the minimum amount of toluene while stirring. After standing overnight it is evaporated and the residue taken up in methanol. The solution is filtered, diluted with water and 6 ml of triethylamine, washed with ethyl acetate, and the washings extracted once with 5% aqueous sodium hydroxide. The combined aqueous solutions are acidified with 5 N hydrochloric acid and the precipitate collected. It is washed with water, triturated with methanol-ethanol and recrystallized from dimethylformamide, to yield the 1-methyl-β-oxo-α-(p-nitrophenylcarbamoyl)-2-pyrrolpropionitrile melting at 245°-250° with decomposition.

Provenance & Evidence