REACTION OF CYANAMIDE WITH ARYL(TRICHLOROMETHYL)CARBINOLS . A NOVEL SYNTHESIS OF ALKYL 5-ARYL-2-IMINO-4-OXO-1-IMIDAZOLIDINECARBOXIMIDATES

The reaction of cyanamide with aryl(trichloromethyl)carbinols in alcoholic potassium hydroxide unexpectedly formed alkyl 5-aryl-2-imino-4-oxo-1-imidazolidinecarboximidates(1), in yields as high as 61%. Several reactions of these compounds are discussed. They can be hydrolyzed with acid to alkyl 1-aryl-2,4-dioxo-1-imidazolidinecarboxylates (3), and with base to either arylhydantoic acids or to α-aminoarylacetic acids depending upon the severity of the reaction conditions. © 1969, American Chemical Society. All rights reserved.