Pyridine → HCID 22287299, compound

Participants

Reaction Steps

2-Acetoxy-2-methylpropanoyl chloride (0.47 ml) was added to a solution of 2-fluoro-4-phenylsulphanylaniline (Method 7) (0.64 g) and pyridine (0.28 ml) in DCM (10 ml). The solution was stirred at ambient temperature for 90 minutes then volatile material was removed by evaporation. The residue was dissolved in methanol (20 ml and a solution of lithium hydroxide monohydrate (0.378 g) in water (2.5 ml) was added. Stirring was continued for another 1 hour then the mixture was acidified to pH 1 with 2M hydrochloric acid and concentrated by evaporation to about 5 ml. Water (10 ml) was added and the product was extracted with ethyl acetate. Organic layers were washed with brine then combined and dried. Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column eluting with 10-20% ethyl acetate/hexane to yield the title compound (0.784 g) as a solid. Mp 91-92.5° C.; NMR: 1.34 (s, 6H), 5.96 (s, 1H), 7.15 (d, 1H), 7.23 (dd, 1H), 7.27-7.4 (m, 5H), 8.02 (t, 1H), 9.3 (s, 1H); MS (ESP−): 304; EA: found: C, 62.8; H, 5.3; N, 4.5; S, 10.5%; C16H16FNO2S requires: C, 62.9; H, 5.3; N, 4.6; S, 10.5%.

Provenance & Evidence