Collect. Czech. Chem. Commun. 1988, 53, 1044-1052

Reactions of methyl esters of N-(2,4-dinitrophenyl)glycine and N-methyl-N-(2,4-dinitrophenyl)glycine with sodium methoxide

Vladimír Macháčeka, Vojeslav Štěrbaa, Ivan Kolbb and Antonín Lyčkab

a Department of Organic Chemistry, Institute of Chemical Technology, 532 10 Pardubice
b Research Institute of Organic Syntheses, 532 18 Pardubice-Rybitví


The reaction of methyl ester of N-(2,4-dinitrophenyl)glycine (I) with sodium methoxide produces 5-nitro-2(3H)benzimidazolone (III). The product identity has been proved by its isolation from the reaction mixture under conditions similar to those of kinetic experiments and by independent synthesis. The reaction of methyl ester of N-methyl-N-(2,4-dinitrophenyl)glycine with methoxide proceeds in two steps, the second one being substantially slower. The first step produces N-methyl-2-nitroso-4-nitroaniline (IV), which can be prepared by this reaction in good yield and purity. N-Methyl-2-nitroso-4-nitroaniline undergoes subsequent reactions in the methoxide solutions. Products of the subsequent reactions have not been identified at the starting ester II concentrations of about 10-4 mol l-1, whereas at higher concentrations of the starting substance the reaction produces 2-amino-2'-methylamino-5,5'-dinitro-ONN-azoxybenzene (V) and 2,2'-bis(methylamino)-5,5'-dinitroazoxybenzene (VI).