Ethanol → HCID 19831183, compound

Participants

Reaction Steps

A solution of 2-chloromethyl-3-carboethoxy-4-(m-nitrophenyl) -5-nitro-6-methyl-1,4-dihydropyridine (1.5 g) in EtOH (15 ml) is added dropwise at 0° C. under N2 atmosphere to a solution of cysteamine hydrochloride (0.9 g) and sodium hydroxide (0.32 g) in EtOH (45 ml). After two hours the solution is acidified (pH≃4) with AcOH, evaporated under reduced pressure and the residue is dissolved in water (50 ml) and extracted with Et2O (2×20 ml). The ethereal extractions are discarded, the water layer is made basic with NaHCO3 and extracted with AcOEt (2×20 ml); the organic phase is washed with water (3×10 ml), dried (Na2SO4), added to a solution of fumaric acid (0.45 g) in MeOH (15 ml), and evaporated to dryness. The residue is crystallized from AcOEt to give 1.9 g of 2-[(2-aminoethyl)thio]methyl-3-carboethoxy-4-(m-nitrophenyl)-5-nitro-6-methyl-1,4-dihydropyridine fumarate (C18H22N4O6S.C4H4O4), m.p. 182°-185° C.

Provenance & Evidence