Sodium Hydroxide → HCID 18468137, compound

Participants

Reaction Steps

A suspension of {5-fluoro-2-[(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiocarbamoyl]-phenoxy}-acetic acid ethyl ester (2.0 g, 4.3 mmol) in ethanol (22 mL) and treated with aq 2 N NaOH (13 mL, 26 mmol). After stirring for 2 h, the solution was concentrated in vacuo to remove most of the ethanol and acidified to pH 1 with aq 2 N HCl. The product was extracted with ethyl acetate and washed with saturated NaCl. The organic layer was dried over MgSO4, filtered and concentrated to give {5-fluoro-2-[(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiocarbamoyl]-phenoxy}-acetic acid as an orange solid (1.05 g, 57%): mp 150° C.; Rf 0.50 (20% methanol in dichloromethane); 1H NMR (DMSO-d6 300 MHz) δ 13.76 (br s, 1 H), 7.83 (br t, J=8.0 Hz, 1 H), 7.79–7.70 (m, 1 H), 7.14 (dd, J1=11.1 Hz, J2=2.4 Hz, 1 H), 6.84 (dt, J1=8.4 Hz, J2=2.4 Hz, 1 H), 5.37 (d, J=5.7 Hz, 2 H), 4.58 (s, 2 H). ESI-LC/MS m/z calcd for C17H10F4N2O3S2: 430.4; Found 429.0 (M−1)−. Anal. calcd for C17H10F4N2O3S2: C, 47.44; H, 2.34; N, 6.51; S, 14.90. Found C, 46.72: H, 2.81: N. 5.85: S, 12.02. Ethanol and water may still have been in the sample for the analytical values to be off.

Provenance & Evidence