p-Toluenesulfonic acid → HCID 57079753, compound

Participants

Reaction Steps

15.9 g (0.1 mole) of 3-oxotetrahydro-2-thiophencarboxylic acid methyl ester, 14.2 g of 2-chloro-3-methylaniline and 200 mg of p-toluenesulfonic acid are heated in 500 ml of toluene for six hours using a water separator. 24.6 g (0.1 mole) of chloranil are then added, and the mixture is boiled for a further one hour. It is cooled and filtered; the filtrate is washed with 100 ml each of 2 N sodium hydroxide solution, sodium dithionite solution and water and concentrated; the residue is purified by column chromatography (silica gel, toluene/ethyl acetate 4/1). 3-(2-Chloro-3-methylanilino)-2-thiophencarboxylic acid methyl ester is obtained as an oil.

Provenance & Evidence