Hydrochloric Acid → HCID 10377841, compound

Participants

Reaction Conditions

Reaction Steps

First, 2-methylsulfonamidoterephthalic acid was prepared as follows. 19.4 g methanesulfonic anhydride was placed in a flask and heated to produce a liquid. 10.3 g dimethyl 2-aminoterephthalate was added to the liquid over a period of 2-3 minutes. The mixture was initially heated at 130° C. for 15 minutes and then at 100° C. for 2 hours and 30 minutes. The mixture was then cooled, 50 ml of cold water added, the mixture stirred for 1 hour and then filtered. The precipitate was recrystallized from 100 ml of methanol which yielded 10 g precipitate having a melting point of 120° C. To a flask were added 1 g of the precipitate, 40 ml of water and 0.6 g potassium hydroxide and the mixture stirred at room temperature. After 15 minutes the slurry became a solution and stirring continued for a total of 12 hours. The solution was then acidified to a pH of about 2 with 6 molar hydrochloric acid to produce a thick precipitate. The precipitate was filtered and dried to yield 0.4 g of a material having a melting point of 296°-298° C. The material was identified by NMR through its potassium salt to be 2-(methylsulfonamido)terephthalic acid.

Provenance & Evidence