Phosphorus sulfide (P2S5) → HCID 22093487, compound

Participants

Reaction Conditions

Reaction Steps

In a flame dried flask under a nitrogen atmosphere, a suspension of phosphorus pentasulfide (2.9 g, 6.4 mmol) in pyridine (26 mL) was treated with {5-Fluoro-2[(4,5,7-trifluoro-benzothiazol-2-ylmethyl)carbamoyl]-phenoxy}-acetic acid ethyl ester (Example 54, 5.7 g, 13 mmol) and heated to 115° C. for 4 h. After cooling to room temperature, the mixture was diluted with water and ethyl acetate. The organic layer was washed successively with 2 N HCl (2×) and saturated NaCl, dried over MgSO4, and concentrated. The resulting brown oil was chromatographed by MPLC (10–100% ethyl acetate in heptane, 23 mL/min, 75 min) to give {5-fluoro-2-[(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiocarbamoyl]-phenoxy}-acetic acid ethyl ester (2.0 g, 34%): 1H NMR (DMSO-d6 300 MHz) δ 10.98 (br s, 1 H), 7.79 (br t, J=6.0 Hz, 2 H), 7.06 (br d, J=11.1 Hz, 1 H), 6.90 (br t, J=9 Hz, 1 H), 5.38 (br s, 2 H), 4.89 (s, 2 H), 4.12 (q, J=7.2 Hz, 2 H), 1.16 (t, J=7.1 3 H).

Provenance & Evidence