Hydrochloric Acid → tert-Butyl {3-[(3-aminobenzyl)thio]phenyl}carbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of iron (0.62 g, 11 mmol) in ethanol (22 mL) was treated with 1 M HCl in water (1.1 mL) and heated at 60° C. for 2 h. The reaction mixture was cooled to 55-60° C. and treated with 5 M ammonium chloride in water (1.9 mL). The reaction mixture was then treated with a solution of tert-butyl {3-[(3-nitrobenzyl)thio]phenyl}carbamate (0.80 g, 2.2 mmol) in ethanol (2.5 mL) while the temperature was kept at 60° C. The resulting suspension was stirred at 60-65° C. for 30 min. The reaction mixture was cooled to 40° C., diluted with ethanol, treated with celite, filtered over a pad of celite, and washed with ethanol. The filtrate was concentrated to a tan solid that was diluted with ethyl acetate (50 mL) and saturated sodium bicarbonate (50 mL). The organic layer was separated and washed with brine (25 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to give a crude tan oil. This material was purified by flash column chromatography to give the desired product (0.63 g, 85%). LCMS for C18H23N2O2S (M+H)+: m/z=331.1.

Provenance & Evidence