Reactions of 4-halo- and 4-methylthio-imidazolium salts with sulfide and methanethiolate ions was written by Begtrup, Mikael. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1979.Application In Synthesis of 4-Bromo-1-methylimidazole This article mentions the following:
The chloroimidazolium salts I [R = H (II), Ph, R1 = Cl, X = 4-MeC6H4SO3] reacted with Na2S-NaH to give the ring cleaved products MeNHC(S)CH2NMeCOR (III; R = H, Ph) and with MeSH-NaH to give the substituted products I [R = H (IV), Ph, R1 = SMe, X = Cl]; further treatment of IV with MeSH-NaH gave the thione V (R = SMe) and after treatment with NaBr, I (R = R1 = H, X = Br). The bromo analog I (R = H, R1 = Br, X = 4-MeC6H4SO3) (VI) reacted with excess Na2S-NaH to give 67% V (R = H) and with 1 mol equiv to give 42% I (R = R1 = H, X = Br), together with V (R = H) and III (R = H); similar treatment of I (R = Ph, R1 = Br, X = 4-MeC6H4SO3) gave 77% I (R = Ph, R1 = H, X = Br). In the Cl series, thiation predominated over ring cleavage, V (R = Cl) being formed when II was treated with Na2S-S. When VI was subjected to similar treatment, reduction with formation of I (R = R1 = H, X = Br) and V (R = H) prevailed over thiation to V (R = Br). Treatment of VI with MeSH-NaH (1 mol equiv) gave 82% I (R = R1 = H, X = Br) whereas with excess MeS–, V (R = H) was obtained. In the experiment, the researchers used many compounds, for example, 4-Bromo-1-methylimidazole (cas: 25676-75-9Application In Synthesis of 4-Bromo-1-methylimidazole).
4-Bromo-1-methylimidazole (cas: 25676-75-9) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Application In Synthesis of 4-Bromo-1-methylimidazole
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem