Acetic Acid → Isohexane ethyl acetate

Participants

Reaction Steps

A mixture of [3-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)phenyl]amine hydrochloride (Example 212, 100 mg, 0.26 mmol) and potassium cyanate (63 mg, 0.78 mol) in acetic acid (3 mL) and water (0.5 mL) was stirred at room temperature for 16 hours. The acetic acid was removed in vacuo and the residue partitioned between ethyl acetate and water. The organic layer was washed with aqueous sodium hydrogencarbonate solution and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 20% ethyl acetate/isohexane then 40% ethyl acetate/isohexane, to give the title compound. δH (500 MHz, d6 DMSO): 8.96 (1H, s), 8.13 (1H, s), 7.86 (2H, d, J=8.5 Hz), 7.79 (2H, d, J=8.5 Hz), 7.67 (2H, dd, J=5.6, 8.7 Hz), 7.54–7.52 (1H, m), 7.44–7.40 (3H, m), 7.27 (1H, d, J=16.4 Hz), 7.22 (2H, t, J=8.8 Hz), 5.98 (2H, s).

Provenance & Evidence