Pyridine → N-(3-amino-2-methoxy-5-trifluoromethyl-phenyl)-methanesulfonamide

Temperature

0 °C

2-Methoxy-5-trifluoromethylbenzene-1,3-diamine (2.32 g, 11.3 mmol) was dissolved in 50 mL anhydrous dichloromethane. The solution was cooled to 0° C., and pyridine (3.64 mL, 45.0 mmol) and methane sulfonyl chloride (0.89 mL, 11.5 mmol) were added. The reaction was left to stir overnight at room temperature. A few more drops (˜0.1 mL) of methane sulfonyl chloride were added and the reaction stirred an extra day. Then 200 mL EtOAc, was added and the solution washed once with 100 mL water, twice with 15 mL saturated aqueous NH4Cl solution and finally with brine. The organic solution was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel using EtOAc/hexanes eluent mixtures, providing N-(3-amino-2-methoxy-5-trifluoromethyl-phenyl)-methanesulfonamide (1870 mg, 6.58 mmol, 58% yield) as an orange solid.

1. waitThe reaction was left
2. stirringthe reaction stirred an extra day
3. washthe solution washed once with 100 mL water, twice with 15 mL saturated aqueous NH4Cl solution and finally with brine
4. dry with materialThe organic solution was dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by column chromatography on silica gel

ORD record

ord-c9af3732abda490ea07deb8d079eaa83

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06872726B2