1-Tert-butyl-4-(isothiocyanatomethyl)benzene → N-(4-t-Butylbenzyl)-N'-{1-methyl-1-[4-(methylsulfonylamino)phenyl]ethyl}thiourea

Participants

Reaction Steps

A suspension of Benzyl N-{1-Methyl-1-[4-(methylsulfonylamino)phenyl]ethyl}carbamate (21-1, 0.5 mmol) and 5% palladium on carbon (100 mg) in MeOH (10 mL) was hydrogenated under a rubber balloon of hydrogen for 1 h. After the solvent was evaporated by rotary evaporator, the residue was dissolved in DMF (5 mL) and treated with 4-t-butylbenzyl isothiocyanate (0.5 mmol). After being stirred overnight, the mixture went to aqueous work-up and the residue was purified by column chromatography on silica gel with EtOAc:hexanes as eluant to afford N-(4-t-Butylbenzyl)-N′-{1-methyl-1-[4-(methylsulfonylamino)phenyl]ethyl}thiourea (21-7, CHK-593)

Provenance & Evidence