S. Farah, R. McCLELLAND
Apr 1, 1993
Citations
0
Influential Citations
5
Citations
Journal
Canadian Journal of Chemistry
Abstract
Treatment of 1-methyl-2-nitroimidazole with bromine in water resulted in rapid dibromination to give 4,5-dibromo-1-methyl-2-nitroimidazole. In dioxane, the bromination was slower, and could be controlled to give 4-bromo-1-methyl-2-nitroimidazole 5 and 5-bromo-1-methyl-2-nitroimidazole 6 in a 4:1 ratio. In an attempt to displace the bromine, the monobromo compounds were treated with cysteamine hydrochloride. In each case the nitro group was displaced instead, the 4-bromo 5 resulting in 2-[(2-aminoethyl)thio]-4-bromo-1-methylimidazole 9 as sole product, and the 5-bromo 6 giving two products identified as the monosubstituted 2-[(2-aminoethyl)thio]-5-bromo-1-methylimidazole 13 and the disubstituted 2,5-bis[2-(aminoethyl)thio]-1-methylimidazole 12. The latter product forms by further reaction of the former and was the sole material observed at long reaction times. A fraction of 12 may also originate from an initial displacement of bromine giving 5-[(2-aminoethyl)thio]-1-methyl-2-nitroimidazole 14, although thi...