4-Chloroaniline → N-[[(4-chlorophenyl)amino]carbonyl]-5-ethyl-2-pyrrolesulfonamide

Participants

Reaction Conditions

Reaction Steps

4-Chloroaniline (4.5 g, 35.4 mmole) was combined with tetrahydrofuran (80 ml) under nitrogen and cooled to -78° C. Chlorosulfonyl isocyanate (3.0 ml, 35.4 mmole) was added and the mixture stirred 1 hour at -78° C. 2-Ethylpyrrole (3.66 g, 38.9 mmole) was added and the mixture allowed to warm to room temperature and then stirred for 2 hours. The reaction was quenched with water and then concentrated. The residue was dissolved in methylene chloride (100 ml) which was extracted with three 100 ml portions of aqueous NaOH. The aqueous layer was acidifed and extracted with methylene chloride. The organic layers were combined and washed with two 100 ml portions of water. The organic layer was then dried over Na2SO4, filtered and concentrated. The resulting dark oil was flashed chromatographed over silica eluding with 4% methanol/methylene chloride. Removal of solvent provided 0.64 g of product.

Provenance & Evidence