Eliel, Ernest L.; Nelson, Kenneth W. published an article in 1955, the title of the article was Reactions of p-chlorobenzenesulfonic acid and derivatives. The σp* constant of the N,N-dimethylsulfonamido group.Synthetic Route of 97-09-6 And the article contains the following content:
In order to find other uses for p-ClC6H4SO3H (I), a by-product in the manufacture of DDT, some experiments are carried out with I. Adding (10 min.) 200 g. ClSO3H to 100 g. dry I at 10°, heating until the evolution of HCl ceases, and pouring the mixture slowly onto ice gives 70-85% p-ClC6H4SO2Cl, m. 51°, which (75 g.) is treated with 28% NH4OH (or 40% NH2Me or 40% NHMe2) at such a rate that the temperature does not exceed 40°, giving 70-80% p-ClC6H4SO2NH2 (II), m. 143-4° [or p-ClC6H4SO2NHMe (III), m. 62-4°, or p-ClC6H4SO2NMe2 (IV), m. 78-9°]. Heating 5 g. IV and 100 cc. 10% NaOH 4 hrs. at 200° in a stainless-steel bomb with shaking gives 91% p-HOC6H4SO2NMe2, m. 94°. p-MeOC6H4SO2NMe2, prepared with CH2N2, m. 71-2°, is also obtained from PhOMe and SO2Cl2 and treatment of the MeOC6H4SO2Cl with NHMe2. Treating 5 g. III with 100 cc. 10% aqueous NaOH 4 hrs. at 200° leaves III unchanged but at 250° PhOH is formed. Heating 7 g. IV with 130 cc. 36% aqueous NH4OH at 250° (about 2700 lb. pressure) 4 hrs. gives 63% p-H2NC6H4SO2NMe2, m. 170.5-1°. Heating 20 g. IV and 10 g. CuCN in 12 cc. C5H5N 4 hrs. at 240-50°, pouring the cooled (100°) mixture into 100 cc. concentrated HCl, stirring the mixture at 20° with 200 cc. C6H6, and evaporating the washed (NH4OH, H2O) C6H6 layer gives 62% p-NCC6H4SO2NMe2 (V), m. 124-7°. Refluxing 2 g. V in 20 cc. 10% NaOH until a homogeneous solution is formed gives 97% p-HO2CC6H4SO2NMe2, m. 251-3°. Refluxing 20 g. V in 100 cc. tetrahydrofuran (THF) 1 hr. with 8 g. LiAlH4 in 50 cc. THF and acidifying the mixture with dilute H2SO4 gives (p-H2NCH2C6H4SO2NMe2)2.H2SO4 not m. below 250°. Adding 20 g. I to 15 cc. 18% fuming H2SO4, 35 cc. concentrated H2SO4, and 30 cc. fuming HNO3, keeping the mixture 1 hr. at 20°, adding 100 cc. H2O, and distilling it off until the temperature reaches 220° gives 11 g. 4,3-Cl(O2N)C6H3SO3H (VI). Heating 10 g. VI with 20 g. ClSO3H 1 hr. at 100° and pouring the cooled mixture onto crushed ice gives 18% sulfonyl chloride (VII) which (3 g.), treated with 50 cc. 28% aq NH4OH, heated to boiling and cooled, yields 79% sulfonamide (VIII), m. 175-7°. Adding 5 g. VII to 25 cc. 40% NHMe2 at such a rate that the temperature does not exceed 40°, filtering the precipitate, and triturating it with 25 cc. concentrated HCl gives 56% N,N-dimethylsulfonamide (IX), m. 100-2°. Heating 3 g. VII with 25 cc. 40% aqueous NHMe2 at 90° gives 84% 4,3-Me2N(O2N)C6H3SO2NMe2, m. 182-3°; 4-methylamino analog, 88%, m. 183°. The reaction rates of 2,4-Cl2C6H3NO2, VIII, IX, and o-ClC6H4NO2 with NaOMe are found to be 1.54, 0.0911, 0.0106, and 0.00306, resp. From the value for VIII σp* for SO2NMe2 is calculated to be 0.99. The experimental process involved the reaction of 3-Nitro-4-chlorobenzenesulfonamide(cas: 97-09-6).Synthetic Route of 97-09-6
3-Nitro-4-chlorobenzenesulfonamide(cas:97-09-6) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Synthetic Route of 97-09-6
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics