Water → Sulfamic acid 3-[2-cyano-1-(3,5-dimethoxy-phenyl)-vinyl]-phenyl ester

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Reaction Steps

To a solution of 3-(3,5-dimethoxy-phenyl)-3-(3-hydroxy-phenyl) -acrylonitrile (280 mg, 1 mmol) in dimethylacetamide (4 mL) was added a solution of sulfamic chloride in methylene chloride (1 mL, 2.3 mmol/mL, 2.3 mmol) at room temperature. After 15 h, water (30 mL) was added to the mixture. The aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layers was washed with water (50 mL), brine (50 mL) and dried over magnesium sulfate. Removal of solvent and chromatography gave (E/Z) sulfamic acid 3-[2-cyano-1-(3,5-dimethoxy-phenyl)-vinyl]-phenyl ester (320 mg, 89% yield): mp, 301-303° C.; 1H NMR (DMSO-d6) δ 3.73 (s, 6H, 2CH3), [3.76 (s)], [6.41 (s)], 6.44 (s, 1H, CH), 6.49-6.51 (m, 2H, Ar), 6.63-6.67 (m, 1H, Ar), 7.22 (brs, 1H, Ar), 7.38-7.65 (m, 3H, Ar), 8.07 (brs, 2H, NH2); Anal. Calcd for C17H16N2O5S+0.1H2O: C, 56.38; H, 4.51; N, 7.73. Found: C, 56.23; H, 4.36; N, 7.55.

Provenance & Evidence