1H-1,2,4-Triazole → HCID 13269108, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 55 g (0.2 mol) of 1-chloro-5-(4-chlorophenoxy)-3,3-dimethyl-2-pentanone in 50 ml of acetone is added dropwise to a mixture of 27.6 g (0.2 mol) of potassium carbonate and 27.6 g (0.4 mol) of 1,2,4-triazole in 400 ml of boiling acetone. The mixture is boiled for a further 3 hours, cooled down to 20° C., filtered and the filtrate is evaporated in vacuo. The oily residue is taken up in 250 ml of ethyl acetate and washed three times with 100 ml of water each time. After drying the organic phase over anhydrous sodium sulphate, it is evaporated in vacupo. the residual crude product (61 g) is dissolved in 250 ml of acetone, and a solution of 57.6 g of naphthalene-1,5-disulphonic acid in 250 ml of acetone is added. The salt which has crystallized out (45.4 g; melting point 188°-190° C.) is suspended in a mixture of 150 ml each of dichloromethane and water and is made alkaline by the addition of 10% strength sodium carbonate solution. The organic phase is separated off, and the aqueous phase is extracted once more with 100 ml of dichloromethane and the combined organic phases are evaporated in vacuo. 30.4 g (49.4% of theory) of 5-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-pentanone are obtained as a pale yellowish liquid of refractive index nD20 =1.5457.

Provenance & Evidence