15862-16-5Relevant academic research and scientific papers
Nitrosation of phenacetin. Formation of N nitroso 2 nitro 4 ethoxyacetanilide as an unstable product of the nitrosation in dilute aqueous acidic solution
Eisenbrand,Preussmann
, p. 1472 - 1475 (2007/10/12)
Reaction of phenacetin with N2O4 in glacial acetic acid at 10° C gives N nitroso 2 nitro 4 ethoxyacetanilide. This N nitrosoacylarylamine is stable at low temperatures (-30° C) but unstable at ambient temperature. No intact N nitroso 2 nitro 4 ethoxyacetanilide can be detected when phenacetin is nitrosated under conditions simulating those in the stomach (37° C, pH 1). Instead, 2 nitro 4 ethoxybenzenediazonium chloride is the main reaction product found. Under the conditions applied, the N nitroso acylarylamine rapidly rearranges by 1,3 migration of the acetyl group. The resulting diazoester dissociates into the corresponding diazonium salt. Trapping of the diazonium ion with 1 naphthol as an azo dye provides a useful means to identify the parent N nitroso compound and to measure colorimetrically its rate of formation. The yields obtained in dilute aqueous nitrosation mixtures are lower than expected; the reasons for this finding are discussed. Preliminary results of animal experiments show that the N nitroso compound is a directly acting carcinogen.
