Cyanoacetamide → Isopropyl 4-(5-cyano-4-(methylthio)-6-oxo-1,6-dihydropyridin-2-yl)benzoate

関与物質

反応手順

A 12% isopropanol suspension of sodium isopropoxide (9.08 g, 13.28 mmol) was added to a mixture of methyl 4-(3,3-bis(methylthio)acryloyl)benzoate (2.5 g, 8.85 mmol) and 2-cyanoacetamide (0.744 g, 8.85 mmol) in isopropanol (50 mL). The resultant mixture was heated to 100° C. for 3 h, cooled to room temperature and quenched with 0.3 N HCl (50 mL). The brown precipitate was collected by filtration, washed with water (10 mL) and dried under vacuum to give isopropyl 4-(5-cyano-4-(methylthio)-6-oxo-1,6-dihydropyridin-2-yl)benzoate (2.3 g, 63% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.70-8.42 (4H, m), 6.67 (1H, br. s), 4.89-5.43 (1H, m), 1.10-1.64 (6H, m); MS (ES+) m/z: 329 (M+H); LC retention time: 3.18 min (analytical HPLC Method A).

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