Octanoyl chloride → HCID 20271342, compound

Participants

Reaction Conditions

Reaction Steps

A solution of octanoyl chloride (4.25 ml, 25 mmole) in dioxane (10 ml) is added dropwise during ten minutes into a stirred suspension of 5-(2-hydroxymethylphenyl)-3-(3-methoxyphenyl)-1H-1,2,4-triazole (2.81 g, 10 mmole) and triethylamine (4.2 ml, 30 mmole) in dioxane (50 ml). After 1 hour, 8% NaHCO3 (50 ml) is added and the reaction mixture is heated to 50° C. for two hours, cooled to room temperature, diluted with water (60 ml) and extracted with methylene chloride. The organic extracts are washed with water, dried over Na2SO4 and concentrated to dryness yielding a raw residue which is purified by silica-gel column chromatography eluting with a mixture 0% to 10% ethyl acetate in toluene and crystallized from isopropyl ether/petroleum ether. Yield: 56.5%. M.p. 61° C. and 87° C. (as a mixture of crystal forms).

Provenance & Evidence