Triethylamine → HCID 21930326, compound

Participants

Reaction Steps

5-Bromo-2-(4-trifluoromethoxy-benzenesulfonylamino)-benzoyl chloride (5.124 g, 11.6 mmol) was dissolved in tetrahydrofuran (100 mL) and the mixture was cooled in an ice bath below 5° C. 2-Methoxy-benzyl amine (1.8 mL, 13.8 mmol, 1.2 equivalents) and triethyl amine (1.9 mL, 13.6 mmol, 1.2 equivalents) were added to the mixture keeping the temperature below 10° C. The mixture was warmed to room temperature and the solvent was removed to dryness. The residue was partitioned between aqueous HCl (1M, 50 mL) and ethyl acetate (100 mL). The organic solvent was collected and concentrated to dryness. The resulting solid was dissolved in ethyl acetate and the solvent removed (2×25 mL). The resulting mixture was purified by column chromatography on silica with an eluent of 20% ethyl acetate in hexane. The solid was suspended in a mixture of 5% ethyl acetate in hexane (90 mL). The mixture was centrifuged and the solid dried at 40° C. overnight in vacuum oven. Recovery=4.85 g (75% yield). M/Z of [M−H]−=557, 1H NMR (CDCl3) δ=3.85 (s, 3H), 4.5 (sd, 2H), 6.5–6.6 (1H), 6.9–7.05 (4H), 7.3–7.4 (2H), 7.45 (1H), 7.5 (1H), 7.6 (1H), 7.8 (2H), 10.8 (br, 1H).

Provenance & Evidence