Water → HCID 13432848, compound

Participants

Reaction Conditions

Reaction Steps

At ambient temperature, 30 g of the product of Step A were dissolved in 1,200 ml of tetrahydrofuran and the solution was cooled to 7° C. Then, 120 ml of 25% of diethyldihydroaluminate in toluene in 120 ml of tetrahydrofuran were added with stirring for 1 hour at 5°-7° C. After returning to ambient temperature, the mixture was stirred for 2 hours, then cooled again to 7° C. after which 120 ml of sodium hydroxide were added slowly with stirring. Then, the mixture was poured into a mixture of 3,600 ml of ethyl acetate and 600 ml of water. Aftering stirring, the aqueous phase was decanted, and the organic phase was washed with an aqueous solution of sodium hydroxide and then with sodium chloride. Each washing solution was extracted with ethyl acetate and the combined extracts were dried and concentrated to dryness to obtain 23.5 g of crude product which was purified by dissolving it at reflux in 220 ml of ethanol. By filtering hot, washing with refluxing ethanol, concentrating to 110 ml under ambient pressure, cooling, separating, washing with ethanol and drying at 60° C., 10.2 g of 4-[5-ethyl-4-(4-methoxyphenyl)-4H-1,2,4-triazol-3-yl]-N-methyl-benzenamine melting at 198.5° C. were obtained.

Provenance & Evidence