Methanol → (4-Thioureido-benzyl)-carbamic Acid Tert-butyl Ester

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Reaction Steps

A mixture of 3 g (13.5 mmol) (4-Amino-benzyl)-carbamic acid tert-butyl ester and 1.81 ml (13.5 mmol) benzoyl isothiocyanate in 60 ml THF was stirred at room temperature for 1 h and afterwards evaporated under reduced pressure. 80 ml MeOH and 5.6 g (40.5 mmol) potassium carbonate in 80 ml water were added and the mixture was stirred at room temperature for 16 h. The mixture was concentrated under reduced pressure and extracted with ethyl acetate. The organic layers were washed with saturated NaHCO3 solution and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica eluting with a gradient of hexane/ethyl acetate to yield after evaporation of the product fractions 3.67 g (97%) of the title compound as yellow amorphous solid.

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