反应详情

A suspension of [5-Fluoro-2-(3-nitro-benzylthiocarbamoyl)-phenoxy]-acetic acid ethyl ester (4.39 g, 11.2 mmol) in ethanol (40 mL) was treated with aq 2 N NaOH (11 mL, 22.4 mmol). After stirring for 4 h, the solution was concentrated in vacuo until most of the ethanol was removed, and the mixture was acidified to pH of 1 with 2 N HCl. After extracting with ethyl acetate, the organic layer was washed with saturated aq NaCl, dried over MgSO4 and concentrated to give [5-fluoro-2-(3-nitro-benzylthiocarbamoyl)-phenoxy]-acetic acid (4.0 g, 98%) as an off-white solid: mp 147-150° C.; Rf 0.27 (20% methanol in dichloromethane); 1H NMR (DMSO-d6 300 MHz) δ 13.23 (s, 1H), 10.79 (t, J=5.7 Hz, 1H), 8.23 (t, J=1.8 Hz, 1H), 8.11 (ddd, J1=8.3 Hz, J2=2.7 Hz, J3=1.2 Hz, 1 H), 7.85 (br d, J=7.5 Hz, 1H), 7.73 (dd, J1=8.9 Hz, J2=7.1 Hz, 1H), 7.63 (t, J=8.1 Hz, 1H), 7.03 (dd, J1=11.4 Hz, J2=2.4 Hz, 1H), 6.86 (dt, J1=8.4 Hz, J2=2.4 Hz, 1H), 5.07 (d, J=5.7 Hz, 2H), 4.83 (s, 2H). ESI-LC/MS m/z calcd for C16H13FN2O5S: 364.4. Found 363.0 (M−1). Anal. calcd for C16H13FN2O5S: C, 52.74: H, 3.60; N, 7.69. Found C, 52.65; H, 3.62; N, 7.58.

1. concentrationthe solution was concentrated in vacuo until most of the ethanol
2. customwas removed
3. extractionAfter extracting with ethyl acetate
4. washthe organic layer was washed with saturated aq NaCl
5. dry with materialdried over MgSO4
6. concentrationconcentrated