Triethylamine → HCID 69198458, compound

Participants

Reaction Steps

To a stirring solution of 1-(4-fluorophenyl)-3-(2-chloroethyl)-4-(4-hydroxyphenyl)azetidin-2-one (Method 12; 0.750 g, 2.35 mmol) in MeCN (10 ml) was added 4-fluorothiophenol (0.500 ml, 4.60 mmol) and triethylamine (0.500 ml, 3.59 mmol) at room temperature. After 20 hours there were still start materiel left (approximately 20%, LC/MS) and more 4-fluorothiophenol (0.250 ml, 2.30 mmol) and triethylamine (0.170 ml, 1.22 mmol) were added. After 24 hours, the solvent was removed under reduced pressure and the residue was partitioned between water (20 ml) and EtOAc (20 ml). The organic layer was washed with brine (5 ml), dried over magnesium sulphate and concentrated. The residue was refluxed in heptane for 30 minutes before the title compound was filtered off as a grey solid (0.946 g; 98%). NMR (CD3OD, 400 MHz) 2.00-2.20 (m, 2H), 3.05 (t, 2H), 3.25 (dt, 1H), 4.75 (d, 1H), 6.75-6.80 (m, 2H), 6.90-7.05 (m, 4H), 7.15-7.40 (m, 6H); m/z: 412.0.

Provenance & Evidence