Hydrochloric Acid → HCID 57152078, compound

Participants

Reaction Conditions

Reaction Steps

3.2 g (16.1 mmol) of cyclohexylmethanesulphonyl chloride (prepared according to J. F. King et al., J. Am. Chem. Soc., 1992, 114 (5), 1743) are added dropwise to a mixture, cooled to −20° C. and under a nitrogen atmosphere, of 2 g (8.18 mmol) of 3,5-dimethyl-4-[(nitromethyl)sulphonyl]aniline, 50 ml of anhydrous tetrahydrofuran and 1.3 ml (16.1 mmol) of pyridine, and the resulting mixture is stirred for 6 hours at −20° C. The mixture is left overnight at −20° C., it is then allowed to warm to room temperature and is stirred for 24 hours at room temperature and then refluxed for 13 hours. The mixture is cooled, poured into water, acidified to pH=3 with 1N HCl, extracted with CH2Cl2, washed with water, dried over Na2SO4, filtered and evaporated under vacuum. The residue is purified by chromatography on silica, eluting with CH2Cl2, and then recrystallized from a hexane/ethyl acetate mixture.

Provenance & Evidence