In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Preparation and reactions of bromo-2-nitro- and bromo-2-aminoimidazoles, published in 1993-04-30, which mentions a compound: 121816-79-3, mainly applied to imidazole bromonitro preparation sulfenylation; methylnitroimidazole bromination; reduction methylnitroimidazole; aminobromomethylimidazole debromination; protodebromination aminobromomethylimidazole; nucleophilic substitution bromonitroimidazole, Reference of 4-Bromo-1-methyl-2-nitro-1H-imidazole.
Treatment of 1-methyl-2-nitroimidazole with Br in H2O resulted in rapid dibromination to 4,5-dibromo-1-methyl-2-nitroimidazole. In dioxane, the bromination was slower, but could be controlled to give 4-bromo-1-methyl-2-nitroimidazole (I) and 5-bromo-1-methyl-2-nitroimidazole (II) in a 4:1 ratio. In an attempt to displace the Br, I and II were treated with cysteamine hydrochloride and in each case the nitro group was displaced: I gave only 2-[(2-aminoethyl)thio]-4-bromo-1-methylimidazole, while II gave 2-[(2-aminoethyl)thio]-5-bromo-1-methylimidazole and 2,5-bis[2-(aminoethyl)thio]-1-methylimidazole (III). III may originate from an initial displacement of Br giving 5-[(2-aminoethyl)thio]-1-methyl-2-nitroimidazole, although this could not be observed due to a rapid further displacement of its nitro group. I and II were reduced to their corresponding amines with Zn/HCl and, when refluxed in H2O in the presence or absence of cysteamine hydrochloride, both underwent protodebromination yielding 2-amino-2-methylimidazole. In D2O, 2-amino-4-bromo-1-methylimidazole was converted into 2-amino-4-deuterio-1-methylimidazole. Bromination of 2-amino-1-methylimidazole in H2O resulted in the formation of cis- and trans-2-amino-4,5-dihydro-4,5-dihydroxyimidazolium ions.
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