Imidazole → Acetamide, N-(2-(2-(2-cyano-4,6-dinitrophenyl)diazenyl)-5-(diethylamino)phenyl)-

Participants

Reaction Steps

A stirred mixture of 3-acetylamino-4-(2'-bromo-4',6'-dinitro phenylazo)-N,N-diethylaniline (4.8 parts), copper (I) iodide (2.0 parts), formaldoxime trimer (1.8 parts), imidazole (1.35 parts), and nitrobenzene (100 parts) was heated to 85° C. for 71/2 hours when thin layer chromatography showed reaction to be effectively complete. Isolation of the product by the method of Example 9 gave 3-acetylamino-4-(2'-cyano-4',6'-dinitrophneylazo)-N,N-diethylaniline (infra red spectrum identical with that of authenic material). When this experiment was repeated using 3.6 parts of imidazole in place of 1.8 parts a considerable amount of 3-acetylamino-4-(2',4'-dinitrophenylazo)-N,N-diethylaniline was produced in addition to the desired 3-acetylamino-4-(2'-cyano-4',6'-dinitrophenylazo)-N,N-diethylaniline.

Provenance & Evidence