3,5-Difluorobenzenesulfonyl chloride

Tan or orange solid

To a stirred solution of 5-(2-(3-fluorophenyl)-3-methylbutyl)-1, 3, 4-thiadiazol-2-amine(175 mg, 0.699 mmol) in DCM (2 mL) was added pyridine (0.848 ml, 10.49 mmol) atRT. To this mixture was added 3, 5-Difluorobenzenesulfonyl chloride (149 mg, 0.699 mmol) and stirred at RT for 1 h.Water was added and the reaction mixture was extracted twice with DCM andcombined organic layers were concentrated under reduced pressure. The crude materialwas purified by reverse phase column chromatography to give racemic 3, 5-difluoro-N-(5-(2-(3-fluorophenyl)-3-methylbutyl)-1, 3, 4-thiadiazol-2-yl)benzenesulfonamide4, 33 mg. LC-MS: m/z [M+H]+:442 1H NMR (400MHz, CHLOROFORM-d) delta: 11, 59 (br s, 1H), 7.24-7.37(m, 3H), 7.03-6.92 (m, 2H), 6.88-6.89 (m, 1H), 6.81 (dt, 1H), 3.35 (dd, 1H), 3.04 (dd, 1H), 2.68-2.74 (m, 1H), 1.87-1.99 (m, 1H), 1.05 (d, 3H), 0.80 (d, 3H)General procedure: To a solution of 1, 3-dihydro-2H-imidazol-2-one (10, 12 mg, 0.143 mmol) in DMF (1 mL) was added at 0 C NaH (60% in mineral oil, 17.1 mg, 0.428 mmol). The suspension was warmed to rt over 30 min and thencooled to 0 C. To this was added ArSO2Cl (0.314 mmol). The solutionwas allowed to warm to rt over 12 h, at which point the reaction was quenchedby addition of brine (1 mL). The aqueous layer was separated and extracted withEtOAc (3×2 mL). The combined organic layers were washed with brine (3 mL), dried over Na2SO4, filtered, and concentrated in vacuo.The crude mixture was purified by column chromatography (gradient 0% to 100%EtOAc in hexanes) to afford bis(arylsulfonyl)dihydroimidazolinones (9a-9ac).

Molecular Weight:212.60
XLogP3:2.1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:211.9510345
Monoisotopic Mass:211.9510345
Topological Polar Surface Area:42.5
Heavy Atom Count:12
Complexity:239
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes