| Route 1 | | the reaction of n-[2-[(5-methyl-4-imidazolyl)methylthio]ethyl]thiourea (i) with methyl iodide in methanol gives the corresponding thiouronium iodide (ii), which is converted into the sulfate by treatment with ira 401 ion-exchange resin. finally, this sulfate is condensed with 4-(3-aminopropyl)imizadole (iii) in refluxing water. | | |  | | List of intermediates | No. | | 4-[(3s,4r)-7-methoxy-2-oxo-3-phenyl-3,4-dihydro-2h-chromen-4-yl]phenyl acetate | (iii) | | ethyl 4-(3-bromopropoxy)-3-methyl-1-benzofuran-2-carboxylate | (i) | | 3-chloro-4-hydroxybenzoic acid methyl ester; methyl 3-chloro-4-hydroxybenzoate | (ii) | | | Reference 1: durant, g.j.; et al.; us 4013659 . Reference 2: serradell, m.n.; hopkins, s.j.; blancafort, p.; castaner, j.; impromidine. drugs fut 1979, 4, 9, 647. |
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