Water → ethyl 3-[(methylsulfonyl)amino]benzoate

Participants

Reaction Steps

To a solution of ethyl 3-aminobenzoate (2.0 g, 12.1 mmol) and sodium hydrogen carbonate (1.2 g, 14.5 mmol) in 1,4-dioxane (24 ml) was added methanesulphonyl chloride (2.3 ml, 30.3 mmol). The mixture was stirred at room temperature for 3 h, before addition of water (10 ml), and the reaction mixture was stirred for a further 5 days. The mixture was partitioned between ethyl acetate and hydrochloric acid (2M) and the organic phase was separated, washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was passed through a plug of silica, eluting with ethyl acetate/cyclohexane [1:3] and the filtrate was concentrated in vacuo to give the title compound (2.4 g).

Provenance & Evidence