Acetic Acid → HCID 86754585, compound

Participants

Reaction Steps

4.3 g of 3-ethyl-2-methyl-5-phenylbenzothiazolium paratoluene sulfonate, 2.7 ml of isophorone, 1 g of ammonium acetate and 3.4 ml of acetic acid were dissolved in 35 ml of toluene and then heated under reflux for 1.5 hours while removing water by azeotropy. After leaving the solution standing to cool to room temperature, 50 ml of water was added. The resulting solution was extracted by 50 ml of methylene chloride, the organic layer was dried over sodium sulfate, the solvent was distilled off, 30 ml of ethyl acetate was added, and 4.7 g of 3-ethyl-2-(3,5,5-trimethyl-2-cyclohexenylidene)methyl-5-phenylbenzothiazolium paratoluene sulfonate produced as a solid was collected by filtration. 4.7 g of the solid obtained and 4.2 g of 1,3-diphenyl-1,3-diazapropene were dissolved in 20 ml of acetic anhydride, the reaction solution was heated under reflux for 8 hours and then left standing to cool to room temperature, 5 g of sodium iodide and 50 ml of water were added, and the resulting solution was extracted by methylene chloride. The organic layer was dried over sodium sulfate and the solvent was distilled off to obtain 2.9 g of 3-ethyl-2-[3-(2-acetanilidoethenyl)-5,5-dimethyl-2-cyclohexenylidene]methyl-5-phenylbenzothiazolium iodide salt as a solid. 0.7 g of the solid obtained and 0.6 g of 2-methyl-3-[2-(1-naphthoxy)ethyl]-5-phenylbenzothiazolium paratoluene sulfonate were dissolved in 10 ml of pyridine at 80° C., and thereto 1 ml of triethylamine was added. The reaction solution was stirred at room temperature for 1 hour, and 30 ml of ethyl acetate was added thereto. The crude crystals produced were collected by filtration and then recrystallized from methylene chloride and isopropyl alcohol to obtain 0.2 g of Compound 39.

Provenance & Evidence