Water → 4-Chloro-3-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-5-ethoxy-benzoic acid

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Reaction Conditions

Reaction Steps

A mixture of 3-amino-4-chloro-5-ethoxy-benzoic acid methyl ester (1.0 g, 4.35 mmol, 1.0 equiv) and divinylsulfone (0.44 mL, 0.51 g, 4.35 mmol, 1.0 equiv) in phosphoric acid 85% (25 mL) was heated to 140° C. overnight. The reaction mixture was poured into water (50 mL) and extracted with dichloromethane (3×50 mL). The combined organic phases were dried over MgSO4, the solvent removed by evaporation under reduced pressure and the crude material purified with column chromatography on silica eluting with heptane/ethyl acetate (1:1+1% acetic acid) yielding 0.18 g (12%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.51 (t, J=7.0 Hz, 3H), 3.25-3.29 (m, 4H), 3.57-3.60 (m, 4H), 4.19 (q, J=7.0 Hz, 2H), 7.44 (d, J=1.7 Hz, 1H), 7.47 (d, J=1.7 Hz, 1H). MS (ISN): 332.1 [M−H]−.

Provenance & Evidence