Hydrochloric Acid → 5-chloro-2-oxo-3-(thiophene-2-carbonyl)-3H-indole-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 429.9 g (2.04 mole) of 5-chloro-2-oxindole-1-carboxamide in 4 liters of N,N-dimethylformamide was added 547.9g (4.48 mole) of 4-(N,N-dimethylamino)pyridine, and then the mixture was cooled to 8° C. To this mixture was added, with stirring, a solution of 328 g (2.23 mole) of thenoyl chloride in 800 ml N,N-dimethylformamide over a 30 minute period, with the temperature being maintained between 8° and 15° C. Stirring was continued for 30 minutes, and then the reaction mixture was poured with stirring into a mixture of 510 ml of concentrated hydrochloric acid and 12 liters of water. Stirring was continued for 2 hours, and then the solid was collected by filtration and washed with water followed by methanol. The solid was dried to give 675.6 g of the title compound.

Provenance & Evidence