Hydrochloric Acid → HCID 15859750, compound

Participants

Reaction Steps

1.3 ml (16.1 mmol) of pyridine, dried over potassium hydroxide, and 2.3 g (12.1 mmol) of 3-methylbenzenesulphonyl chloride are successively added to a solution, maintained under a nitrogen atmosphere, of 2.0 g (8.19 mmol) of 3,5-dimethyl-4-[(nitromethyl]sulphonyl]aniline in 50 ml of anhydrous tetrahydrofuran. The reaction medium is stirred for 24 h at room temperature and then maintained at 40° C. for 1 h, after which it is poured into a mixture of 100 ml of water and 100 g of ice. This mixture is acidified to pH 3 by addition of 1N hydrochloric acid and is extracted with 3 times 100 ml of methylene chloride. The combined organic extracts are washed with 100 ml of water, dried over sodium sulphate and concentrated to dryness under reduced pressure. The residue obtained is purified by chromatography on a column of silica (eluent: methylene chloride) to give 2.3 g (71%) of N-[3,5-dimethyl-4-[(nitromethyl)sulphonyl]phenyl]-3-methylbenzenesulphonamide.

Provenance & Evidence