Trifluoroacetic acid → 2-(4,4-Dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-4-fluorobenzonitrile

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Reaction Steps

To a solution of 4-fluoro-2-(5-(4-methoxybenzyl)-4,4-dimethyl-1,1′-dioxido-1,2,5-thiadiazolidin-2-yl)benzonitrile (4.6 g, 11.81 mmol) in dichloromethane (30 mL) was added trifluoroacetic acid (2.73 mL, 35.4 mmol) and the mixture stirred at room temperature for 18 h. The mixture was diluted with methanol and the white solid collected by filtration and discarded. The cloudy solution was concentrated and the resulting solid was triturated with methanol and then filtered to give the title compound as a white solid (3.18 g, 100% yield). LCMS (M+H) calcd for C11H13FN3O2S: 270.07; found: 270.00. 1H NMR (300 MHz, CDCl3) δ: 7.66 (0.2H, dd, J=8.8, 5.8 Hz), 7.58 (1H, dd, J=9.5, 2.6 Hz), 7.10-7.04 (1H, m), 4.48 (1H, brs), 3.85 (2H, s), 1.55 (6H, s).

Provenance & Evidence