Hydrochloric Acid → HCID 20271354, compound

Participants

Reaction Steps

A mixture of 5-(2-hydroxymethylphenyl)-3-(3-ethoxyphenyl)-1H-1,2,4-triazole (2.36 g, 8 mmole) and octanoyl chloride (1.6 ml, 9.4 mmole) in 1,2-dichloroethane (24 ml) is heated to the reflux temperature with stirring. When the reaction, which is followed by thin layer chromatography (silica-gel plates, toluene: ethyl acetate 1:1), is complete, the reaction mixture is cooled to room temperature and methanol (8 ml) is added. Then an excess of NaHCO3 (1.21 g, 14.4 mmole) is added to neutralize the hydrochloric acid formed during the reaction, followed, after a few minutes, by anhydrous K2CO3 (0.062 g, 0.45 mmole). When the partial transesterification of the N,O-diacyl derivative into the desired monoacyloxy one is complete, the reaction mixture is diluted with water (20 ml), the organic phase is separated and the aqueous one is extracted with methylene chloride (2×10 ml). The organic extracts are combined, washed with water, dried over Na2SO4 and concentrated to dryness giving a row residue which is purified by crystallization from hexane. Yield: 61%. M.p. 87°-89° C.

Provenance & Evidence