Triethylamine → Hexanoic acid, 6-[(4-aminophenyl)thio]-, methyl ester

Participants

Reaction Steps

To a solution of 4-aminothiophenol (2.4 g, 18.9 mmol) in methanol (10 mL) was added triethylamine (2.70 mL, 19.2 mmol). A solution of 6-bromohexanoic acid methyl ester (3.0 g, 18.9 mmol) and tert-butylammonium iodide (350 mg, 0.95 mmol) in methanol (5 mL) was added. The mixture was stirred at room temperature for 16 hours and then concentrated under reduced pressure. The residue was taken up in ethyl acetate (100 mL) and water (100 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate (100 mL), distilled water (100 mL) and brine (100 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a yellow oil that was purified by flash chromatography (2:8 to 1:1 ethyl acetate:40-60° C. petroleum ether) to give the title compound (3.0 g, 62%) as a colourless oil.

Provenance & Evidence