Methyl iodide → HCID 68454305, compound

Participants

Reaction Steps

A suspension of sodium hydride (0.16 g, 55% w/w) was washed free of mineral oil and taken up in DMF (5 mL). The solution was cooled in an ice bath while a solution of 3-[2-(4-isopropyl-3-methyl-phenoxy)acetylamino]benzoate (0.80 g, 2.34 mmol) in DMF (10 mL) was added. The mixture was allowed to stir for 1 h, then was treated with methyl iodide (0.60 g), and the resulting mixture stirred overnight. It was diluted with ethyl acetate (50 mL), and this was washed with three 50 mL portions of water and then brine. The aqueous phases were back-extracted in sequence with ethyl acetate, and the organic extracts were combined, dried over anhydrous magnesium sulfate, filtered, and evaporated. The residue was separated by column chromatography to afford the product, methyl 3-[N-[2-(4-isopropyl-3-methylphenoxy)-acetyl]-N-methylamino]-benzoate, as a pale yellow oil (0.68 g, 1.91 mmol, 82%). 1H NMR (CDCl3, 300 MHz): δ 8.03 (1H, d, J=7.6 Hz), 7.90 (1H, t, J=2.1 Hz), 7.51 (1H, t, J=7.9 Hz), 7.44 (1H, dd, J=8.0, 1.7 Hz), 7.06 (1H, dd, J=9.1, 5.3 Hz), 6.59–6.52 (1H, m), 4.38 (2H, s), 3.93 (3H, s), 3.32 (3H, s), 3.02 (1H, m, J=7.0 Hz), 2.25 (3H, s), 1.15 (6H, d, J=7.0 Hz). Mass spectrum (ES+): m/z 357 (22), 356 (100).

Provenance & Evidence