Sodium hydride → 2-Methylthio-3-nitro-1,4,5,6-tetrahydropyridine

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Reaction Steps

A mixture of 1-nitro-2-methylthio-2-(3-bromopropylamino)ethylene (3.2 g, 0.012 mol) and sodium hydride (50% in oil, 0.9 g, 0.019 mol) in dry tetrahydrofuran (50 ml) was refluxed for 18 hours. The mixture was filtered, and the filtrate was evaporated to dryness. The residue was chromatographed on a silica gel column, the product being eluted with ethyl acetate. Recrystallisation of the product from methanol/propan-2-ol gave 2-methylthio-3-nitro-1,4,5,6-tetrahydropyridine (0.6 g, 29%) m.p. 230.5°-231.5°. Found: C, 41.5; H, 5.7; N, 16.1; S, 18.25; C6H10N2O2S requires: C, 41.4; H, 5.8; N, 16.1; S, 18.4%.

Provenance & Evidence