Ethyl Acetate → HCID 67461620, compound

Participants

Reaction Conditions

Reaction Steps

Mix 2-(4-chloro-phenyl)-4-(2-hydroxy-ethyl)-thiazole-5-carboxylic acid 2,4-dimethoxy-benzylamide (19.7 g, 45.5 mmol) with EtOAc (400 mL) and treat the resulting slurry with 1-hydroxy-1-oxo-1H-benzo[d][1,2]iodoxol-3-one (36.0 g, 57.8 mmol). Stir the mixture at 60° C. for 1.5 h. Add additional 1-hydroxy-1-oxo-1H-benzo[d][1,2]iodoxol-3-one (18.0 g, 28.9 mmol) and stir the mixture at 70° C. overnight. Cool the mixture to room temperature and then dilute with CH2Cl2 (600 mL). Filter the mixture and wash the solids with additional CH2Cl2 (3×500 mL). Wash the filtrate with NaHCO3 (4×300 mL) and water (300 mL). Dry the organic portion, filter, and concentrate in vacuo. Purify the crude material by flash chromatography, using 0.5% MeOH/CH2Cl2 as eluent, to give 13.1 g (70%) of the title compound as a light yellow-orange solid. 1H NMR (400 MHz, CDCl3) δ7.99 (d, 2H, J=8.1), 7.50 (d, 1H, J=7.4), 7.45 (d, 2H, J=8.8), 7.38 (d, 1H, J=8.8), 6.84 (d, 1H, J=6.4), 6.46 (m, 2H), 5.16 (s, 2H), 3.84 (s, 3H), 3.78 (s, 3H).

Provenance & Evidence