Prepn. of 5-nitro-imidazole deriv. esp. 1-methyl-2-isopropyl cpd. - by reaction of 1-amino-2-nitro-ethylene cpd. and a N-halo-amidine, to give antimicrobial, antibacterial and amoebicide

摘要

Prepn. of nitroimidazole derivs. of formula (I) by reaction of 1-amino-2-nitroethylene cpd. (R2)2N-CH=CH-NO2 (II) with a N-haloamidine of formula RNH-CR1=NX (III) is claimed. R = opt branched, opt. unsaturated, 1-8C monovalent aliphatic hydrocarbyl group, which is opt. substd. by one or more aryl (pref. phenyl, alpha- or beta- naphthyl), halo, hydroxy, 1-4C alkoxy, aryloxy, nitro or perhaloalkyl e.g. CF3; R1 is an R group or 6-10C aryl opt. substd. by one or more substituents, such as lower alkyl, hydroxy, lower alkoxy, nitro, opt. alkylated, arylated or acylated amino, carboxy and alkoxycarbonyl; the two R2 gps. independently are lower alkyl (e.g. methyl, ethyl, propyl) or 5-6C cycloalkyl or the 2 groups together with N atom form a satd. heterocyclic opt. contg. further heteroatoms e.g. pyrrolidino, piperidino, morpholino or N-methylpiperazino and X=halo pref. Cl. (I) are antimicrobials e.g. bactericides active against Trichomonas and amoebicides. A pref. cpd. is 2-isopropyl-1-methyl-5-nitroimidazole(ipronidazole) used to treat Histomonas meleagridis infections and which has good activity against E. histolytica, Trichomonas vaginalis and Trichomonas foetus. The present process gives high yields (5-70%) of pure prod. which is readily isolated and avoids toxic by-products and difficutly controllable reactions found in known processes.