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. Name: 3-Nitro-4-chlorobenzenesulfonamide
Kulka, Marshall published an article in 1950, the title of the article was Derivatives of p-chlorobenzenesulfonic acid.Name: 3-Nitro-4-chlorobenzenesulfonamide And the article contains the following content:
In the manufacture of DDT from PhCl and Cl3CCHO (H2SO4 as condensing agent), p-ClC6H4SO3H is a byproduct; derivatives have been prepared to be tested as possible insecticides and fungicides. p-ClC6H4SO3Na (I) (335 g.) in 700 cc. CHCl3, treated (15 min.) with 370 g. ClSO3H at a rate to maintain a temperature of 60° and then heated 6 h. at 55-60°, gives 89% p-ClC6H4SO2Cl (II), b12 140°, m. 52-3°. FSO3H (200 g.) in an Al beaker, treated dropwise (3 h.) with 57 g. PhCl at 48-50° and stirred and heated an addnl. 4 h., gives 74% ClC6H4SO2F (III), m. 48-9°, and 2.5 g. (p-ClC6H4)2SO2, m. 146-7°. I (100 g.), 200 g. FSO3H, and 150 cc. CCl4, heated 24 h. at 70-5° and the acid layer heated and stirred another 24 h. with fresh CCl4, gives 85% III. III (50 g.), added (10 min.) to 125 cc. HNO3 (d. 1.5) and 50 cc. concentrated H2SO4 at 60° and heated and stirred 1.25 h. at 65°, gives 10 g. III and 67% 3-nitro-4-chlorobenzenesulfonyl fluoride, b17 165-6°, m. 51-2°; with liquid NH3 it gives 85% of the amide, m. 175-6°. III (100 g.), added to 300 g. Na2SO3 in 1000 cc. H2O at 70° and heated 5 h. at 70-80° and a few min. at 100°, gives 81% p-ClC6H4SO2H (IV), m. 98-9°; 1 mol. II, reduced at 55-60° with 2 1. 28.5% aqueous Na2SO3, gives 60% IV; 2 1. of a 31.5% solution gives 80% IV. The Na salt from 27 g. IV in 150 cc. hot EtOH and 35 g. 3,4-Cl2C6H3CH2Cl, refluxed 8 h., gives 68% p-chlorophenyl 3,4-dichlorobenzyl sulfone, m. 135-6°; p-xylylene bis(p-chlorophenyl) disulfone, m. 335-7°, 78%. IV (72 g.) and 45 g. Na2CO3 in 900 cc. H2O, added to 61 g. Cl2CHCO2H and heated 44 h. on the steam bath, give 65% p-chlorophenyl chloromethyl sulfone, m. 120-1°. III (25 g.) and 35 cc. ClCH2CH2OH, treated with 7 g. NaOH and heated 3 h. at 20-5°, give 93% 2-chloroethyl p-chlorobenzenesulfonate, b13 197°, nD20 1.5465 (II gives 47%). III (13 g.), 10 g. Cl3CCH2OH, 3 g. NaOH, and 40 cc. ether, kept 3 h. at 22-5°, give 87% 2,2,2-trichloroethyl p-chlorobenzenesulfonate, m. 73-4° (63% from II and Cl3CCH2OH on refluxing 8 h.). III and HOCH(CH2Cl)2 give 25% 1,3-dichloro-2-Pr p-chlorobenzenesulfonate (V), b14 190-200°, m. 53-4°. II (106 g.) in 50 cc. C5H5N, treated with 28 g. HOCH2CH(OH)CH2Cl (VI) (temperature below 100°) and heated 1 h. on the steam bath, give 38 g. V and 9 g. ClCH(CH2Cl)2. II (106 g.) in 50 cc. C5H5N, treated (15 min.) with 28 g. VI at 25-35°, stirred 0.5 h. at 30-5° and kept 4 h. at room temperature, give 84% 3-chloropropylene bis(p-chlorobenzenesulfonate) (VII), m. 66-7°; VII and II in C5H5N at 100° give a mixture of VI and ClCH(CH2Cl)2. 2,4-Cl2C6H3OH (16.3 g.) and 4 g. NaOH in 40 cc. H2O, treated with 19.5 g. III and heated 2 h. at 50-60°, give 85% 2,4-dichlorophenyl p-chlorobenzenesulfonate, m. 119-20°. ClCH2CH2OH (20 cc.) and 50 g. 3,4-Cl2C6H3SO2Cl (VIII), treated dropwise (0.5 h.) with 17 g. C5H5N at 10-15°, stirred an addnl. hr. at 10-15°, and kept 2 h. at 5°, give 81% 2-chloroethyl 3,4-dichlorobenzenesulfonate (IX), m. 69-70°. VIII and excess ClCH2CH2OH on refluxing give a poor yield of IX. p-ClC6H4SO2NHCH2CH2OH (X) (5 g.) and 10 g. SOCl2, refluxed 2 h., give 2 g. N-(2-chloroethyl)-p-chlorobenzenesulfonamide, m. 152-3°. II (1 mol.) in CHCl3, treated dropwise with 1 mol. amine at a temperature below 40° and then with 1 mol. aqueous NaOH, and stirred an addnl. 0.5 h., gives a nearly quant. yield of the following p-chlorobenzenesulfonamides: N,N-di-Me, m. 79-80°; N,N-di-Et, m. 37-8°; N-iso-Pr, m. 85-6°; N-Bu, m. 50-1°; X, m. 104-5°. 4-(p-Chlorophenylsulfonyl) morpholine, m. 148-9°; N,N’-bis (p-chlorophenyl-sulfonyl)-1,2-diaminopropane, m. 141-2°. II (50 g.) and a trace of Fe2(SO4)3, treated 1 h. with Cl at 175-80°, gives 63% p-C6H4Cl2 and 4 g. 1,2,3,5-C6H2Cl4. The experimental process involved the reaction of 3-Nitro-4-chlorobenzenesulfonamide(cas: 97-09-6).Name: 3-Nitro-4-chlorobenzenesulfonamide
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. Name: 3-Nitro-4-chlorobenzenesulfonamide
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics