Potassium Carbonate → 2-{2-[(2-tert-Butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]ethoxy}phenyl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

2-[(2-tert-Butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]ethyl 4-methylbenzenesulfonate (150 mg, 0.313 mmol) was dissolved in dry MeCN (3 mL) under nitrogen atmosphere. 2-Hydroxyphenyl methanesulfonate (65 mg, 0.345 mmol) was added followed by potassium carbonate (217 mg, 1.567 mmol). The reaction mixture was heated in a microwave reactor at 120° C. for 15 mins. Potassium carbonate was filtered off and the reaction mixture was evaporated to dryness in a vacuum centrifuge. The crude product was purified by preparative HPLC affording the title compound (94 mg, 58.5%). 1H NMR (CDCl3, 500 MHz): δ 1.71 (s, 9H), 3.19 (s, 3H), 3.26 (q, 2H), 3.92 (t, 2H), 5.86 (t, 1H), 6.86 (d, 1H), 6.99 (t, 1H), 7.22 (t, 1H), 7.28 (d, 1H), 7.42-7.45 (m, 3H), 7.49-7.53 (m, 2H); 13C NMR (CDCl3, 125 MHz): δ 27.82, 38.53, 43.28, 61.78, 67.18, 108.11, 114.66, 122.30, 124.66, 125.15, 128.54, 129.08, 130.04, 131.69, 135.27, 138.61, 150.49, 159.51; Mass Spectrum: M+H+ 494.8.

Provenance & Evidence