Synthesis of N-derivatives of p-quinonimines was written by Titov, E. A.;Avdeenko, A. P.. And the article was included in Zhurnal Organicheskoi Khimii in 1972.Formula: C13H13NO3S This article mentions the following:
N,2-Bis(benzenesulfonyl)- and N-benzenesulfonyl-2-chloro-1,4-naphthaquinone imine and N-benzenesulfonyl-2,6-dichloro-1,4-benzoquinone imine were prepared in ≤95.5% yield by treating the corresponding sulfonamido phenols with either HNO3 or NaNO2-HOAc. -PhSO2NHC10-H6OH-1 was converted to 54.2% 4-benzenesulfonamido-1,2-naphthoquinone by the former procedure and 65.0% N-benzenesulfonyl-1,4-naphthoquinone imine by the latter. N-(2,4-Dinitrophenyl)-4-aminophenol was oxidized by Pb(OAc)4 in HOAc to the corresponding quinone imine, which gave N-(2,4-dinitrophenyl)-2-chloro-4-aminophenol (I) with HCl-HOAc; N-(2,4-dinitrophenyl)-2,6-dichloro-4-aminophenol and -1,4-benzoquinone imine were prepared analogously from I. -Benzenesulfonamido- and 4-(p-toluenesulfonamido)-2-nitrophenol were prepared by nitration of the parent sulfonamido phenols using NaNO2-HOAc. -Benzenesulfonamido- and 1-(p-toluenesulfonamido)naphthalene gave mixtures of the resp. 2- and 4-nitro derivatives with HCl-NaNO2, with the latter predominating. In the experiment, the researchers used many compounds, for example, N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6Formula: C13H13NO3S).
N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. Amides can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.Formula: C13H13NO3S
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics