Halogenation of N-substituted p-quinone imines and p-quinone oxime esters: IV. Chlorination and bromination of N-arylsulfonyl-2(3)-methyl(2-chloro)-1,4-benzoquinone monoimines was written by Avdeenko, A. P.;Konovalova, S. A.. And the article was included in Russian Journal of Organic Chemistry in 2006.Application of 1146-43-6 This article mentions the following:
The addition of halogens to N-arylsulfonyl-1,4-benzoquinone imines (e.g. N-(4-oxo-2,5-cyclohexadien-1-ylidene)benzenesulfonamide), which exist in a solution as Z and E isomers, is controlled by steric factors. Z-E isomerization strongly affects the stability of cyclohexene structures formed by halogenation of 1,4-benzoquinone imines. The halogenation of N-arylsulfonyl-1,4-benzoquinone imines is accompanied by prototropic rearrangement. The halogenation of analogous phenols, e.g. N-(4-hydroxyphenyl)benzenesulfonamide, which were also obtained in the halogenation of the quinone imines, was also examined In the experiment, the researchers used many compounds, for example, N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6Application of 1146-43-6).
N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6) belongs to amides. Amides can be viewed as a derivative of a carboxylic acid RC(=O)OH with the hydroxyl group –OH replaced by an amine group −NR′R″; or, equivalently, an acyl (alkanoyl) group RC(=O)− joined to an amine group. Amides are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.Application of 1146-43-6
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics