Dimethyl Sulfoxide → 4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole

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Reaction Steps

Triphenyl β-acetylvinylphosphonium bromide (4.11 g, 0.01 mole) was added in one portion to a stirred suspension of 1.1 g (0.01 mole) of formamidine sulfinic acid in 20 ml of dimethylsulfoxide containing 0.25 g of sodium hydride. The mixture was stirred at ambient temperature for 1 hour then at 80° for an additional hour. A solution of 0.99 g (0.01 mole) of the sodium salt of cysteamine, prepared by addition of two equivalents of sodium methoxide to cysteamine dihydrochloride, in 10 ml of methanol was added and the resulting mixture was heated at 70°-80° for 4 hours. The mixture was diluted with twice its volume of water and the triphenyl phosphine was removed by filtration. The filtrate was extracted with 100 ml of toluene and with two 100 ml portions of chloroform. The chloroform extracts were combined, dried and evaporated to dryness to give 4-(2-aminoethyl)thiomethyl-5-methylimidazole in 45% yield.

Provenance & Evidence