1H-1,2,4-Triazole → HCID 13176306, compound

Participants

Reaction Steps

89 g (0.28 mol) of 5-bromo-5-(4-chlorophenoxy)-3,3-dimethylpent-1-en-4-one, dissolved in 120 ml of acetonitrile, were added dropwise, in the course of 30 minutes, to a solution of 115.9 g (1.68 mols) of 1,2,4-triazole in 1,000 ml of acetonitrile at 50° C. After the solution had been heated at the boil for three hours, the solvent was distilled off and the residue was taken up in 300 ml of ethyl acetate. The solution was washed three times with 50 ml of water, and the organic phase, after having been dried over anhydrous sodium sulphate, was concentrated by evaporation under reduced pressure. The residual oil was dissolved in 400 ml of acetone, and a solution of 80.6 g of naphthalene-1,5-disulphonic acid in 400 ml of acetone was added. The salt which had crystallized out was filtered off under suction and washed with acetone, 250 ml each of water and dichloromethane were stirred with the salt, and the mixture was then rendered alkaline with a 10% strength sodium carbonate solution. The oil which remained after the organic phase had been evaporated off was dissolved in a small amount of ether, and petroleum ether was then slowly added to the solution. The product which crystallized out in the process was filtered off and washed with a small amount of ether/petroleum ether. 17.1 g (20% of theory) of 5-(4-chlorophenoxy)-3,3-dimethyl-5-(1,2,4-triazol-4-yl)-pent-1-en-4-one (Compound 3) of melting point 124° to 126° C. were obtained.

Provenance & Evidence