Reaction of hydrogen bromide with N-p-tolyl- and N-p-tosyl-1,4-benzoquinone monoimines was written by Toropin, N. V.;Burmistrov, K. S.;Burmistrov, S. I.;Zaichenko, N. L.. And the article was included in Zhurnal Organicheskoi Khimii in 1986.Computed Properties of C13H13NO3S This article mentions the following:
Oxybromination of 6 benzoquinone imines I (R = 4-tolyl, 2,4-BrMeC6H3, 4-tosyl; R1-R3 = H, Br; R4 = H) gave 7-80% I (same R; R1-R4 = H, Br). Brominating 4-RNHC6H4OH (R = 4-tolyl, 4-tosyl) followed by oxidation gave I (same R; R1-R3 = H, Br; R4 = H). In the experiment, the researchers used many compounds, for example, N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6Computed Properties of C13H13NO3S).
N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water. 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.Computed Properties of C13H13NO3S
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics