4-[(Methylsulfonyl)amino]benzoyl chloride → HCID 20225364, compound

Participants

Reaction Steps

To 2.72 g (11.1 mmole) of 4-[(methylsulfonyl)amino]benzoyl chloride in 50 ml of tetrahydrofuran cooled to 0° C. under an N2 atmosphere add dropwise 2.04 g (11.1 mmole) of N-(2-aminoethyl)-2,2,6,6-tetramethylpiperidine. After the addition is complete, allow the reaction to stir at ambient temperature overnight. Monitor the progress of the reaction by thin layer chromatography on silica gel (acetonitrile: ammonium hydroxide; 9:1). When the reaction is complete, remove the solvent in vacuo. Dissolve the resulting oil in 50 ml of water. Add 50% sodium hydroxide until pH=14. Wash aqueous with 3×50 ml of diethyl ether. To aqueous layer add concentrated hydrochloric acid until pH=9. Extract with 3×50 ml of methylene chloride. Combine extracts and dry over sodium sulfate. Remove solvent in vacuo. Dissolve resulting oil in methanol and bubble hydrogen chloride gas through the solution until pH 1 is reached. Remove the solvent in vacuo. Recrystallize the solid in methanol/ethyl acetate to provide the title compound.

Provenance & Evidence