N-acetyl-o-toluidine → 3-Acetamido-4-methylbenzene-1-sulfonyl chloride

Participants

Reaction Conditions

Reaction Steps

Chlorosulfonic acid (500 g.) was taken in a three neck round bottom flask equipped with a guard tube and cooled it to 10° C. N-acetyl 2-toluidine (100 g.) was added in small portions maintaining temperature below 10° C. After complete addition of 2-methoxy acetanilide cooling is removed and reaction was brought to 25° C. Reaction mixture was stirred at 25° C. for further 24 hours. After the completion of reaction (TLC), the reaction mixture was poured on ice-water, and the resulting slurry was filtered on buchner funnel. Solid cake on funnel was washed with 500 mL of water and the resulting solid was dried on phosphorus pentoxide in a desiccator to obtain 113.5 grams off white solid. It was found to contain a mixture of two isomers as confirmed from NMR and HPLC; however the desired isomer was obtained by partial crystallization using benzene and used for further experimentation, after the thorough carectorisation.

Provenance & Evidence