Chloroacetylation of p-toluidine (I) gives N-chloroacetyl-p-toluidine (II), which by reaction with 3-methyl-4-chlorophenol in refluxing acetone - K2CO3 is converted into 2-(4-chloro-3-methylphenoxy)-N-(p-tolyl)acetamide (III). The reaction of (III) with Lawesson's reagent in boiling toluene affords the thioamide (IV), which is methylated with methyl iodide in refluxing acetone - K2CO3 and the resulting 5-methyl ether without any further purification is finally subjected in situ to cyclocondensation by treating with ethylcarbazate in refluxing DMF to give IDPH-85184 in an overall yield of 40%.

Chloroacetylation of p-toluidine (I) gives N-chloroacetyl-p-toluidine (II), which by reaction with 3-methyl-4-chlorophenol in refluxing acetone - K2CO3 is converted into 2-(4-chloro-3-methylphenoxy)-N-(p-tolyl)acetamide (III). The reaction of (III) with Lawesson's reagent in boiling toluene affords the thioamide (IV), which is methylated with methyl iodide in refluxing acetone - K2CO3 and the resulting 5-methyl ether without any further purification is finally subjected in situ to cyclocondensation by treating with ethylcarbazate in refluxing DMF to give IDPH-85184 in an overall yield of 40%.