Sulfonamides. I. “Marfanil” and its ο- and p-isomers was written by Angyal, S. J.;Jenkin, S. R.. And the article was included in Australian Journal of Scientific Research in 1950.Product Details of 857003-88-4 The following contents are mentioned in the article:
A new synthesis of “Marfanil” (p-H2NCH2.C6H4SO2NH2) from p-MeC6H4SO2Cl is described. The ο- and m-isomers were also prepared and found to have low bacteriostatic activity. p-ClCH2C6H4SO2Cl, prepared (23% yield)by chlorinating com. p-MeC6H4SO2Cl at 160°, was added with stirring to alc. NH3 and the product precipitated with H2O to give 86% p-ClCH2C6H4SO2NH2. With hexamine in cold EtOH, this formed p-sulphamylbenzylhexaminium chloride (96%; low Cl content), decomposing at 180°, which on refluxing 30 min. with concentrated HCl in EtOH furnished 85% marfanil, m. 148°, [sulfate, m. 254-5° (decomposition)]. The original synthesis from AcNHCH2Ph (C.A. 38, 5805.6; 34, 6587.8) was also studied. PhCH2NHAc (977 g.) was added to ClSO3H (2.1 l.) below 20°, the mixture heated 1 hr. at 70°, cooled, added to 10 kg. ice, and the resulting oil decanted and added to concentrated NH4OH (2 l.) and H2O (one l.) below 40°, to give 47% acetylmarfanil and 9% ο-(acetamidomethyl)benzenesulfonamide-HCl (I), m. 137-8°. I refluxed 8 hrs. in EtOH with concentrated HCl gave 82% ο-(aminomethyl)benzenesulfonamide-HCl, m. 238-9° [free base (II), m. 83-4°]. Attempted crystallization of II from Me2CO produced the isopropylene derivative, C10H14O2SN2 (83%), m. 136°. m-H2NC6H4SO2NH2 (17.2 g.) was diazotized in 23 ml. concentrated HCl and 50 ml. H2O with 7.6 g. NaNO2 in H2O and the mixture added below 20° to 12 g. CuCl2 and 16 g. NaCN in 100 ml. water (the temperature finally raised to 70°) to give 9 g. (50%) m-NCC6H4SO2NH2 (III), m. 148-50°. III was reduced (H, Pd/C) in the presence of NH3 to 60% m,m’-disulfamyldibenzylamine, m. 176.5-7° (HCl salt, m. 216-18°), while in aqueous HCl, 57% m-(aminomethyl)benzenesulfonamide-HCl, m. 232° (free base, an oil), resulted. There was no correlation between basic strength and antibacterial action of marfanil and its ο- and p-isomers, whose pK values were found to be resp. 8.52, 10.08 (literature, 8.18, 10.23); 8.53, 10.11; 8.55, 10.14. This study involved multiple reactions and reactants, such as 3,3′-(Azanediylbis(methylene))dibenzenesulfonamide (cas: 857003-88-4Product Details of 857003-88-4).
3,3′-(Azanediylbis(methylene))dibenzenesulfonamide (cas: 857003-88-4) 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 can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Product Details of 857003-88-4
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics