Acetonitrile → 4-Chloro-N-methyl-3-nitro-N-octadecylbenzamide

Participants

Reaction Steps

After adding 68.6 g of thionyl chloride to a mixture of 105.7 g of 3-nitro-4-chlorobenzoic acid and 800 ml of acetonitrile, the mixture was refluxed for 4 hours. After cooling the reaction mixture, the solvent was distilled off therefrom and the residue formed was dissolved in chloroform. To the solution was added 63.5 g of triethylamine and after adjusting the temperature thereof to 5° C., a chloroform solution of 148.6 g of N-methyloctadecylamine was added dropwise to the solution to perform reaction. After the reaction was over, water was added to the reaction mixture, and the organic phase thus formed was recovered and dried over anhydrous sodium sulfate. After filtering off inorganic materials, the solvent was distilled off from the filtrate and the residue was recrystallized from a 1:3 mixture of acetonitrile and methanol to provide 186 g of the desired compound with a yield of 76.0%. The melting point thereof was 55° C. to 56° C.

Provenance & Evidence