This compound can be obtained in several different ways: 1) The condensation of imidazole (I) with 4-(2-chloroethoxy)benzamide (II) by means of NaH in DMF gives 1-[2-(4-carbamoylphenoxy)ethyl]imidazole (III), which is hydrolyzed by refluxing with 5N aqueous HCl. 2) Esters of 4-(2-chloroethoxy)benzoic acid (IV) can also be used instead of (II) in the first step of the synthesis. 3) This compound can also be obtained by direct condensation of imidazole (I) with 4-(2-chloroethoxy)benzoic acid (IV) by means of NaH in THF.
A new synthesis of dazoxiben has been described: The condensation of methyl 4-hydroxybenzoate (I) with 1,2-dibromoethane (II) by means of NaOH gives methyl 4-(2-bromoethoxy)benzoate (III), which is hydrolyzed with H2SO4 to the corresponding free acid (IV). Finally, this compound is condensed with imidazole (V) in refluxing butanol.