1,5-Bis(p-chlorophenyl)-1,4-pentadien-3-one → HCID 73791714, compound

Participants

Reaction Conditions

Reaction Steps

A mixture consisting of 6 grams of 1,5-bis(p-chlorophenyl)- 1,4-pentadien-3-one, 3.6 grams of 2-imidazolin-2-ylhydrazine hydrobromide, 10 drops of 48 percent aqueous hydrobromic acid and 80 ml. of n-propanol is stirred and heated at reflux for two hours. The reaction mixture is then concentrated to about one-half its volume and cooled at -10° C. The yellow crystalline precipitate is collected, washed with ether, and then added to a slight excess of aqueous 2N sodium hydroxide. The resultant free base is collected, dried, dissolved in ether and treated with a slight excess of 7.2 N n-propanolic hydrogen⟦,⟧ chloride, yielding the title compound melting at 239°-240° C. If the original hydrobromide salt is recrystallized from methanol, a product containing one mole of methanol of crystallization is obtained, melting at 206.5°-208.5° C.

Provenance & Evidence