116059-06-4Relevant academic research and scientific papers
o-Nitroaniline Derivatives. Part 12. The Reaction of N-(2,4-Dinitrophenyl)-sarcosine Ethyl Ester with Bases: Some Novel Redox Processes Revealed by X-Ray Crystallography
McFarlane, Michael D.,Smith, David M.,Ferguson, George,Kaitner, Branko
, p. 893 - 902 (2007/10/02)
According to the base used, the title reaction gives, either 2-amino-2'-methylamino-5,5'-dinitro-ONN-azoxybenzene (9) or 2,2'-bis(methylamino)-5,5'-dinitrooazoxybenzene (10), together with 1-hydroxy-4-methyl-7-nitroquinoxaline-2,3-dione (13).Reaction of compound (13) with thionyl chloride gives 5-chloro-1-methyl-6-nitroquinoxaline-2,3-dione (12).Possible mechanisms for these novel reactions are discussed.The structures of (i) the diacetyl derivative of the azoxy compound (9), (ii) compound (12), and (iii) the monohydrate of (13), have been established by X-ray crystallography.All three compounds give monoclinic crystals.Compound (8) has space group P21/n, with 4 molecules in a cell of dimensions a = 19.949(4), b = 10.289(4), c = 9.101(2) Angstroem, β = 97.98(2) degree; R = 0.030 for 1270 reflections.Compound (12) has space group P21/c, with 4 molecules in a cell of dimensions a = 6.922(1), b = 10.857(3), c = 13.192(2) Angstroem, β = 100.87(1) degree; R = 0.055 for 956 reflections.Compound (13)*H2O has space group C2/c, with 8 formula units in a cell of dimensions a = 16.130(3), b = 7.173(1), c = 18.215(3) Angstroem, β = 97.67(2) degree; R = 0.037 for 1244 reflections.
REACTIONS OF METHYL ESTERS OF N-(2,4-DINITROPHENYL)GLYCINE AND N-METHYL-N-(2,4-DINITROPHENYL)GLYCINE WITH SODIUM METHOXIDE
Machacek, Vladimir,Sterba, Vojeslav,Kolb, Ivan,Lycka, Antonin
, p. 1044 - 1052 (2007/10/02)
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 andpurity.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).
