Acetonitrile → N-[4-(2-Formylhydrazinyl)phenyl]-3-nitrobenzene-1-sulfonamide

Participants

Reaction Conditions

Reaction Steps

1 1 of N,N-dimethylacetoamide, 880 g of acetonitrile, and 285 g of triethylamine were added to and dissolved in 426 g of 2-(4-aminophenyl)-1-formylhydrazine under an atmosphere of nitrogen. The solution was cooled to -5° C., and 625 g of meta-nitrobenzenesulfonyl chloride was gradually added to the solution. During the addition, the mixture was agitated under cooling so that the temperature did not exceed -5° C. The resultant mixture was cooled at a temperature below -5° C. for 1.5 hours, then the temperature thereof was raised to a room temperature. Extraction was performed with 12 l of ethyl acetate and 12 l of saturated salt water. The organic layer was separated and then concentrated to 6 l. 3 l of n-hexane was added to the concentrate, and the obtained mixture was agitated at a room temperature for 30 minutes. The produced crystals were filtered off and washed with 500 g of ethyl acetate.

Provenance & Evidence