Acetic Anhydride → (E)-3-methoxy-2-nitro-6-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridine

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Reaktionsschritte

A mixture of 2-((5-methoxy-6-nitropyridin-2-yl)methylsulfonyl)acetic acid (0.29 g, 1.0 mmol) in dry toluene (2 mL) was added 2,4,6-trimethoxybenz-aldehyde (0.196 g, 1.0 mmol) and acetic anhydride (0.38 mL). After refluxing for 5 hrs, the reaction mixture was evaporated to dryness. The residue was precipitated by adding methanol (15 mL). The precipitate was filtered to give 150 mg (35%) the titled compound as grey coloured powder. 1H-NMR (Acetone-D6): δ 3.92 (s, 9H, 3×OCH3), 4.07 (s, 3H, OCH3), 4.52 (s, 2H, CH2), 6.32 (s, 2H, Ph-H), 7.20 (d, J=15.6 Hz, 1H, CH), 7.74 (d, 1H, J=15.6 Hz, CH), 7.87 (d, 1H, J=8.4 Hz, Py-H), 7.95 (d, 1H, J=8.8 Hz, Py-H); HR-MS (ESI+) m/z 425.1053 [M+1]+ C18H20N2O8S requires 424.0940.

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