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

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.

1. concentrationconcentrated under reduced pressure
2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate (100 mL)
3. distillationdistilled water (100 mL) and brine (100 mL)
4. dry with materialdried over anhydrous MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customto give a yellow oil that
8. customwas purified by flash chromatography (2:8 to 1:1 ethyl acetate:40-60° C. petroleum ether)

ORD record

ord-ce2817019fa2495c87aa763ad5943428

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683185B2