Hettler, Hans published the artcileCharacterization of primary and secondary amines with pseudosaccharin chloride, Safety of 3-Aminobenzo[d]isothiazole 1,1-dioxide, the publication is Fresenius’ Zeitschrift fuer Analytische Chemie (1966), 220(1), 9-15, database is CAplus.
Pseudosaccharin chloride (I) treated with primary and secondary amines (RR’NH) gave amidine-type compounds (II) which were also obtained by reaction of amines with pseudosaccharin ethers (III). Methods used for the preparation were: (1) The pure amine or a solution [for sparingly soluble amines, solution in CO(NMe2)2 was used] was treated with I in an inert solvent (C6H6) and II precipitated by addition of H2O; (2) A 2% aqueous solution of the amine was shaken with a solution of I in C6H6 until II separated; (3) II precipitated when an aqueous solution of the amine was treated with a dioxane solution of I; (4) Reaction of III with the amine in MeCN, gave II after several hrs. at room temperature Using these methods the tabulated derivatives were prepared The Rf values were determined by thin layer chromatography on silica gel using 85:15 C6H6-MeOH. R, R’, Method, M.p., % yield, Rf; H, Me, 2, 303° (MeOH), 52, 0.44; H, Et, 2, 286° (MeOH), 73, 0.47; H, CH2CH2OH, 1, 246°, (MeCN), 79, 0.375; H, (CH2)9Me, 1, 73°, (cyclohexane), 79, 0.87; H, (CH2)13Me, 4, 145° (MeOH), 100, 0.645; H, (CH2)17Me, 1, 142°, (Me2CO), 92, 0.615; H, CH2CH:CH2, 2, 220° (Me2CO), 63, 0.395; H, (CH2)6NH (pseudosaccharin group), 3, 350° (CO(NMe2)2), -, 0.0; H, tert-u, 1, 255° (MeOH), 46, 0.36; H, p-MeC6H4CH2, 1, 228° (Me2CO-petr. ether), 98, 0.48; H, cyclohexyl, 1, 258° (MeCN), 96, 0.395; H, Ph, 1, 324° (MeCN), 99, 0.435; Et, Et, 1, 215° (MeCN), 96.5, 0.36; cyclohexyl, cyclohexyl, 1, 259° (MeOH), 99, 0.660; Ph, Ph, 1, 260° (MeOH), 96, 0.715; CH2CH2OH, CH2CH2OH, 3, 165° (MeCN), 65, 0.275; H, H, 4, 312° (Me2CO), 100, 0.35; H, NH2, 1, 245° (MeOH), 100, 0.42; Piperidine reacted with I (method 4) to give 100% II (NRR’ = piperidino), m. 211° (MeCN). Morpholine (method 1) gave 87.5% II (NRR’ = morpholino), m. 234° (MeCN). Ph2C:NOH (method 1) gave 73% (IV), m. 165° (MeCN).
Fresenius’ Zeitschrift fuer Analytische Chemie 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, Safety of 3-Aminobenzo[d]isothiazole 1,1-dioxide.
Referemce:
https://en.wikipedia.org/wiki/Isothiazole,
Isothiazole – ScienceDirect.com