Isatoic Anhydride → HCID 20085591, compound

Participants

Reaction Steps

Isatoic anhydride (2.65 g; 0.0162 mol) was slowly added to a room temperature solution of 5.51 g (0.0162 mol) of 2-(aminomethyl)-1-tritylimidazole in 30 ml of methylene chloride and 65 ml of isopropanol. The reaction mixture was then allowed to react overnight. The next morning the solution was reduced to dryness under reduced pressure and the resultant residue was redissolved in an ethyl acetate/aqueous sodium bicarbonate mixture. The resulting layers were separated, the organic layer was washed with water and then a saturated sodium chloride solution, dried over anhydrous sodium sulfate and finally reduced to dryness to provide a yellow solid. This solid was filtered through silica gel using 1000 ml of methylene chloride followed by 1000 ml of a 2% methanol in methylene chloride solution. The resulting filtrate was reduced to dryness to provide a white solid. This solid was recrystallized from a 1:1 ethyl acetate/hexanes solution to provide 5.95 g of the desired subtitled intermediate (m.p 171°-175° C.).

Provenance & Evidence