Question

The structure of sulfasalazine, a drug used to treat both ulcerative colitis and rheumatoid arthritis, is shown below.

i. Using the conditions described in the protocol posted on canvas (Experiment 5), write a complete reaction scheme for the synthesis of sulfasalazine from an aniline starting material and a coupling reagent.

ii. Draw the diazonium salt product formed from the reaction between the aniline shown in part i and HONO (nitrous acid).

iii. Draw the full arrow-pushing mechanism for the coupling reaction (EAS) between the diazonium salt (part ii) and the proposed coupling agent (part i) to generate sulfasazaline. Note: you do not need to write a mechanism for the diazotization of the aniline.

Answer 1

mechanism- aromatic electrophilic substitution reaction -