Barr, C. R. published the artcileThe reaction of 3-(chlorosulfonyl)benzoyl chloride with amines, Related Products of isothiazole, the publication is Journal of the American Chemical Society (1951), 4131-3, database is CAplus.
cf. U.S. patent 2,484,477, C.A. 44, 7695f. m-ClCOC6H4SO2Cl (I) can react with 2 different amines in 2 stages. The carboxamide is formed in the 1st reaction, the sulfonamide in the 2nd. This property is used to prepare, (1) mixed amides of the type RR’NCOC6H4SO2NR”R”’, and (2) pure compounds containing SO3H groups. PhNH2 (1.80 g.) in 20 cc. dry PhMe added during 10 min. to 5.28 g. I in 50 cc. boiling PhMe, and the mixture refluxed 30 min. and kept 2 hrs. at 10° yielded 5.3 g. m-(chlorosulfonyl)-benzanilide (II), fine, white needles from PhMe, m. 155-6°. PhNH2 (3.8 g.) in 30 cc. PhMe added dropwise to 4.8 g. I in 50 cc. PhMe, the mixture stirred overnight, filtered, and the solid stirred into 500 cc. water yielded 4.5 g. II, m. 155-6°. PhNH2 (3.8 g.) in 30 cc. PhMe added dropwise to 4.8 g. I in 50 cc. PhMe, and the mixture refluxed 1.5 hrs., and let stand overnight yielded 6 g. m-sulfobenzoic acid dianilide (III), m. 176-7°. II and PhNH2.HCl (1 mole of each) yielded III. PhNH2 (0.63 g.) added to I g. II in 10 cc. PhMe at room temperature, the mixture heated to 90°, cooled to room temperature, and diluted with 20 cc. water yielded III, m. 176-7° (from PhMe and alc.). II (1 g.) refluxed 1 hr. water and the solution concentrated on the steam bath yielded quantitatively m-(phenylcarbamyl)benzenesulfonic acid (IV). PhNH2 (2 cc.) and 1 g. IV in 10 cc. 90% EtOH with 2 cc. Et2O yielded 1 g. PhNH2 salt of IV, white needles, m. 249-51°. I (23.9 g.) added to 21.8 g. o-H2NC6H4OH in 350 cc. dioxane, the mixture filtered after 15 min., the solid washed with 50 cc. dioxane, and the filtrate diluted with 400 cc. hexane yielded 24 g. 3-(chlorosulfonyl)-2′-hydroxybenzanilide (V), small, tan crystals from (CHCl2)2, m. 183° (decomposition). V (1 g.) stirred into 5 cc. PhNH2 and the excess PhNH2 removed with 100 cc. 10% HCl yielded 0.8 g. 3-(phenylsulfamyl)-2′-hydroxybenzanilide (VI), fine, white needles from PhMe, m. 170°. The procedure used for VI with 5 g. V and 10 g. MeHNPh yielded 5 g. of the 3-(methylphenylsulfamyl) compound, m. 158° (from PhMe). p-H2NC6H4OH (2.9 g.) and 0.04 mole NaOAc in 50 cc. AcOH heated 5 min. on the steam bath, the solution treated with 4.78 g. I in 50 cc. AcOH, and the mixture heated 1.75 hrs. on the steam bath, chilled 15 min. at 0°, and diluted with 500 cc. water yielded 5.24 g. 3-(chlorosulfonyl)-4′-hydroxybenzanilide, m. 170°. 1-Phenyl-3-amino-5-pyrazolone (C.A. 36, 6536.8) (10 g.) stirred 20 min. on the steam bath with 10.6 g. m-O2NC6H4– COCl and 7 cc. (CO2Et)2, and the mixture refluxed and stirred with 5O cc. EtOH and cooled yielded 14.5 g. 1-phenyl-3-(m- nitrobenzamido)-5-pyrazolone (VII), m. 215-20°. VII (16 g.) refluxed in 145 cc. AcOH, 15 cc. water, and 80 cc. EtOH, 16.0 g. powd. Fe added at once, the mixture boiled 10 min., filtered hot, and the filtrate diluted with 100 cc. water and cooled without stirring yielded 11.0 g. 1-phenyl-3-(m-amino- benzamido)-5-pyrazolone (VIII), lustrous, brown crystals, m. 220-2°. VIII (2.94 g.) and 1.64 g. NaOAc in 55 cc. AcOH (at 50°) added to 2.39 g. I in 25 cc. AcOH, the mixture stirred 3 hrs. at room temperature, filtered, washed with 100 cc. water, and stirred into 300 cc. water yielded 5.2 g. 1-phenyl-3-{m-[m-(m-chlorosulfonyl)benzamido] benzamido}-5-pyrazolone, white crystals m. 188-90° (containing 1 mole AcOH). I (6.6 g.) added all at once to 4.4 g. 1-aminoanthraquinone in 130 cc. hot PhMe, and the mixture refluxed 1.25 hrs. and cooled to room temperature yielded 6.9 g. 1-[m-(chlorosulfonyl)-benzamidolanthraquinone, long amber neeldes from PhMe, m. 219-22° (decomposition).
Journal of the American Chemical Society published new progress about 7668-28-2. 7668-28-2 belongs to isothiazole, auxiliary class Sulfamide,Amine,Benzothiazole, name is 3-Aminobenzo[d]isothiazole 1,1-dioxide, and the molecular formula is C7H6N2O2S, Related Products of isothiazole.
Referemce:
https://en.wikipedia.org/wiki/Isothiazole,
Isothiazole – ScienceDirect.com