Pyridine → HCID 21930318, compound

Participants

Reaction Steps

2-Amino-5-bromo-N-(2-methoxy-benzyl)-benzamide (9 g, 28 mmol) was suspended in anhydrous dichloromethane (300 ml) and cooled in ice bath. Pyridine (20 ml) was added with stirring, followed by addition of 2-nitro-4-trifluoromethyl-benzene sulfonyl chloride (15 g, 52 mmol). The reaction mixture was allowed to stir at room temperature for 2 days. The mixture was filtered to remove a solid precipitate and the filtrate was evaporated to dryness. Aqueous HCl (2N, 300 ml) was added, and the resulting solution was extracted with dichloromethane (500 ml). The organic layer was concentrated and the resulting residue was dissolved in ethyl acetate. Addition of hexanes to this solution produced a solid precipitate. This solid was dissolved in ethyl acetate and passed through a short column of silica using an eluent of dichloromethane and ethyl acetate to provide the desired product (7.5 g, 46% yield). M/Z of [M−H]−=587.1 1H NMR (DMSO) δ=3.8 (s, 3H), 4.35 (sd, 2H), 6.85 (1H), 6.95 (1H), 7.1 (1H), 7.2 (1H), 7.4 (1H), 7.65 (1H), 8 (1H), 8.15 (1H), 8.25 (1H), 8.55 (1H).

Provenance & Evidence