Schwenker, Gerhard’s team published research in Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft in 303 | CAS: 7668-28-2

Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 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 C7H7IN2O, Synthetic Route of 7668-28-2.

Schwenker, Gerhard published the artcileInfrared spectroscopic studies of tautomerizable amidines. I. N-sulfonylamidines and 3-amino-1,2-benzisothiazole 1,1-dioxides, Synthetic Route of 7668-28-2, the publication is Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft (1970), 303(12), 980-7, database is CAplus and MEDLINE.

According to ir spectroscopic data, open-chained N-sulfonylamidines and amino-benzisothiazole 1,1-dioxides exist in the crystalline state and solution in the amino form R2SO2N:CR3NRR1 (I) and II, resp. The bathochromic shift of the SO2 and C:N stretching bands and investigation of the N-H region indicate that the SO2 group is involved in the amidine mesomerism and that intramol. H bonds are present in I. Investigated were the following I (R, R1, R2, and R3 given): H, H, Me, Me; H, H, Ph, Ph; H, H, C6H4Me-p, Ph; H, Me, C6H4Me-p, Ph; H, Ph, C6H4Me-p, Ph; H, H, C6H4NO2-p, Me; H, H, C6H4NO2-p, Ph; H, Me, C6H4-NO2-p, Ph; H, H, C6H4NH2-p, Ph; H, H, C6H4NHAc-p, Ph; and II (R and R1 given): H, H; H, Me; H, C6H13; H, cyclohexyl; H, Ph; (RR1 = ) (CH2)5.

Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 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 C7H7IN2O, Synthetic Route of 7668-28-2.

Referemce:
https://en.wikipedia.org/wiki/Isothiazole,
Isothiazole – ScienceDirect.com

Derkach, G. I.’s team published research in Zhurnal Obshchei Khimii in 32 | CAS: 7668-28-2

Zhurnal Obshchei Khimii 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, Quality Control of 7668-28-2.

Derkach, G. I. published the artcileDerivatives of phosphorylated amidines, Quality Control of 7668-28-2, the publication is Zhurnal Obshchei Khimii (1962), 1878-82, database is CAplus.

cf. CA 56, 3405d. Refluxing 3-amino-1,2-benzisosulfonazole (Ia) with 1.25 moles PCl5 in C6H6 until HCl evolution had stopped, followed by evaporating in vacuo, gave I (R = N:PCl3), m. 165-9°, which refluxed 1 hr. with H2O gave Ia. The trichloride and glacial AcOH in C6H6 gave after brief refluxing and 12 hrs. at room temperature I (R = NHPOCl2), m. 213-14°. Similarly the trichloride and 6 moles PhNH2 in C6H6 gave I [(R = N:P(NHPh)3], m. 214-15°; with EtNH2, I [R = N:P(NHEt)3], m. 171-2° with 4 moles PhNH2 in C6H6, I [R = NHPO(NHPh)2], m. 260-1°. Refluxing I [R = N:P(NHPh)3] 15 min. in 96% EtOH gave I [R = NHPO(NHPh)2]. I (R = NHPOCl2) with EtNH2 in C6H6 gave after brief refluxing I [R = NHPO(NHEt)2], m. 219-20°; similarly was prepared I [R = NHPO(NHC6H4Cl-p)2], m. 249-53°. Also reported was I [R = NHPO(OPh)2], m. 257-9°. p-O2NC6H4C(:NSO2Ph)NH2 and PCl5 similarly gave p-O2NC6H4C(:NSO2Ph)N: PCl3 (II), an oil, which with AcOH in C6H6 2 hrs. at 40° gave p-O2NC6H4C(:NSO2Ph)NHPOCl2, m. 161-3°, which with PhNH2 gave p-O2NC6H4C(:NSO2Ph)NHPO(NHPh)2, m. 221-2°. Reaction of II with PhONa in dioxane gave p-O2NC6H4C(:NSO2Ph)NHPO(OPh)2, m. 154-6°.

Zhurnal Obshchei Khimii 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, Quality Control of 7668-28-2.

Referemce:
https://en.wikipedia.org/wiki/Isothiazole,
Isothiazole – ScienceDirect.com

Mohamed, Abdalla R.’s team published research in Bioorganic Chemistry in 107 | CAS: 7668-28-2

Bioorganic Chemistry 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, Application of 3-Aminobenzo[d]isothiazole 1,1-dioxide.

Mohamed, Abdalla R. published the artcileDesign, synthesis and in silico insights of new 7,8-disubstituted-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione derivatives with potent anticancer and multi-kinase inhibitory activities, Application of 3-Aminobenzo[d]isothiazole 1,1-dioxide, the publication is Bioorganic Chemistry (2021), 104569, database is CAplus and MEDLINE.

7,8-Disubstituted-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione I [R1= Ph, phenylcarbamoyl, p-tolylcarbamoyl, etc.; R2 = bromo, (2,4-dioxo-1H-pyrimidin-6-yl)amino] were selected based on the characteristic pharmacophoric features required for PI3K and B-Raf oncogenes inhibition was synthesized. All the synthesized compounds were evaluated for their in-vitro anticancer activity. I [R1= phenyl; R2 = (2,4-dioxo-1H-pyrimidin-6-yl)amino] and I [R1=p-tolylcarbamoyl; R2 = bromo] displayed an acceptable potent activity according to the DTP-NCI and were further evaluated in the NCI five doses assay. To validate the design, compounds with the highest mean growth inhibition percent were screened against the target PI3Kα and B-RafV600E confirmed their multi-kinase activity. The tested compounds showed promising multi-kinase activity. I [R1= phenyl; R2 = (2,4-dioxo-1H-pyrimidin-6-yl)amino] and I [R1=p-tolylcarbamoyl; R2 = bromo] anticancer effectiveness and multi-kinase activity against PI3Kα and B-RafV600E were consolidated by the inhibition of B-RafWT, EGFR and VEGFR-2 with IC50 in the sub-micromolar range. Further investigations on the most potent I [R1= phenyl; R2 = (2,4-dioxo-1H-pyrimidin-6-yl)amino] and I [R1=p-tolylcarbamoyl; R2 = bromo] were carried out and studied their safety on normal cell line, in-silico profiling and predicted ADME characteristics.

Bioorganic Chemistry 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, Application of 3-Aminobenzo[d]isothiazole 1,1-dioxide.

Referemce:
https://en.wikipedia.org/wiki/Isothiazole,
Isothiazole – ScienceDirect.com

Mameli, Efisio’s team published research in Gazzetta Chimica Italiana in 70 | CAS: 7668-28-2

Gazzetta Chimica Italiana 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, Product Details of C7H6N2O2S.

Mameli, Efisio published the artcilePyrolysis of ammonium saccharin and of ammonium thiosaccharin. Saccharinimine and pseudosaccharinamine, Product Details of C7H6N2O2S, the publication is Gazzetta Chimica Italiana (1940), 855-74, database is CAplus.

The work is a continuation of that on the comparative behavior of saccharin (I) and thiosaccharin (II) (cf. M.-M., C. A. 29, 3998.8). Various modifications of the Defournel method of preparing NH4 saccharin (III) were tried, including temperature, concentration, and proportion of reagents. At 170°, III loses its crystallinity; at 210° it softens and evolves NH3; at 222° it melts; at 233-5° the evolution of NH3 increases and a brown liquid is formed; at 240-60° NH3 is no longer evolved, and a yellow-brown, vitreous mass remains. The latter, extracted with Et2O (to remove I), then with water, the aqueous extract evaporated, the residue extracted with Et2O, and purified from boiling water, yields 33% of 0-C6H4(CONH2)SO2ONH4 (IV), m. 257-60° (cf. various m. ps., e. g., Ber. 22, 759 (1889); Am. Chem. J. 18, 825(1896); 30, 370(1903)). After the Et2O and water extractions, a solid substance remains, which, purified by boiling water, yields 50% of C6H4.SO2.NH.C:NH (V), m. 315°. NH4 thiosaccharin (VI) was prepared by a method already described (cf. M.-M., C. A. 10, 1174) and by new methods (II and (NH4)2CO3, II and urea, II and thiourea, etc.), which will be published later. At 170°, VI evolves NH3, H2S and unidentified vapors; at 225°, evolution of gases is more intense; at 224-50° the mass reddens; at 285° the residue softens and contracts; at 295-300° it melts to a dark liquid, and evolves H2S. Elimination of H2S is usually complete at 270°. The residue, extracted with Et2O and then with water, as before, does not yield IV. The final residue is V. To compare V with the supposedly identical compound already known, it was prepared by 8 methods: (1) pyrolysis of III; (2) pyrolysis of VI; (3) heating I and (NH4)2CO3 at 250°; (4) heating II and (NH4)2CO3 at 300°; (5) heating I and urea at 250°; (6) heating II and urea at 150°; (7) action of NH3 on chloropseudosaccharin, and (8) pyrolysis of saccharin oxime. Methods (3), (4) and (5) are new, and the details will be published later. The yield by method (1) was 50%; that by method (2) was 80-85%. The products by all methods m. 315°. An extensive study of V was carried out. Its crystalline form depends on the conditions of crystallization; but all forms m. 315° and have the same solubility and chem. properties, so the different forms are polymorphic rather than tautomeric. Aqueous solutions of V are slightly acid to litmus. It is insoluble in dilute or concentrated HCl, dilute or 60% H2SO4, aqueous alkali carbonates, and dilute NH4OH. It is soluble in 10% NaOH and KOH, slightly soluble in concentrated NH4OH and 6% aqueous alkalies. V is precipitated from its alk. solutions by acids and by CO2, whereas I and II are precipitated from their alk. solutions by acids but not by CO2. In 30% aqueous alkalies, V dissolves in part, and in part forms alkali salts, which dissolve only by dilution with water. The earlier discovery that cold aqueous alkalies hydrolyze V to I and NH3 (cf. M.-M., C. A. 29, 3998.8) was confirmed, and it was further found that when V and 5% NaOH are allowed to stand several days or are heated 2 h., o-C6H4(SO2NH2)CO2H is formed. Because of the behavior of V with aqueous alkalies, it was impossible to prepare alkali salts. When aqueous or alc. NaOH or KOH solutions of V were allowed to evaporate, I was obtained, and when alc. NH3 solutions were evaporated, V was recovered. Hot aqueous V does not reduce NH3-AgNO3, but precipitates the Ag salt, C7H5O2N2SAg, of V. The best method is to dissolve V in a min. of 10% NaOH or preferably NH4OH, and precipitate by excess AgNO3 solution The fact that V is less acidic than I is shown also by their behavior toward 5KBr-KBrO3 mixtures and 5KI-KIO3 mixtures I liberates Br and I; V liberates neither (II gives a precipitate which was not studied). V is slightly soluble in cold AcOH, PhNH2 and C5H5N, and readily soluble in hot PhNH2, hot C5H5N, cold concentrated H2SO4 and 80% H2SO4, from all of which solutions it is precipitated unaltered by addition of water, whereas II and C5H5N react. When KNO2 is added to a solution of V in concentrated or 80% H2SO4, there is no reaction. V does not react with H2S, (NH4)2S, BzH, piperonal or PhCH:CHCHO at room temperature, or with AlCl3 or Na2SO4 at 200°. Hot aqueous V does not reduce NH3-AgNO3, but precipitates the Ag salt, C7H5O2N2SAg, of V, which is not altered by prolonged boiling of the liquid It can be prepared also by dissolving V in a min. of 10% NaOH, or preferably NH4OH, and adding excess AgNO3. The instability of alk. solutions of V made it impossible to prepare its Na and NH4 salts. V in dilute EtOH, NH2OH.HCl (4 mols.) and NaOAc (4 mols.), heated 90 min., yields saccharin oxime, m. 208-10° (cf. M.-M., C. A. 27, 2682). The results in general point to the constitution of V as C6H4.SO2.NH.C:NH, rather than C6H4.SO2.N:CNH2, i. e., pseudosaccharinamine, which was supposed to have the constitution of the probably identical compound, m. 315°, prepared otherwise by Jesurum (Ber. 26, 2294, 2298(1893)) and by others. In the same way, the iminoamide of saccharincarboxylic acid, prepared by Zincke and Greune (C. A. 16, 2322) should have the constitution: H2NCOC6H3.SO2.NH.C:NH, rather than H2NCOC6H3.SO2.N:CNH2. The transformation of III and of VI as described has few precedents, either with respect to the formation of IV or of V; in fact the formation of V from III and from VI is a new type of transposition, in which III and VI lose H2O and H2S, resp., following which a group containing N migrates from a N atom to an adjacent C atom, thus: The transformation of O:C:NNH4 to O:C(NH2)2, involves only migration of a group containing N from a N atom to a C atom, without dehydration. If this were true of III, the product would be NCNH2 or HN:C:NH. Nor is the transformation of the -CONHCO- group to the -C(:NH)OCO-group, which takes place in the pyrolysis of imides, analogous to the pyrolysis of III.

Gazzetta Chimica Italiana 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, Product Details of C7H6N2O2S.

Referemce:
https://en.wikipedia.org/wiki/Isothiazole,
Isothiazole – ScienceDirect.com

Riggin, R. M.’s team published research in Food and Chemical Toxicology in 21 | CAS: 7668-28-2

Food and Chemical Toxicology 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, Category: isothiazole.

Riggin, R. M. published the artcileCharacterization of impurities in commercial lots of sodium saccharin produced by the Sherwin-Williams process. II. Mutagenicity, Category: isothiazole, the publication is Food and Chemical Toxicology (1983), 21(1), 11-17, database is CAplus and MEDLINE.

All individual components identified in solvent extracts of specific manufacturing lots of saccharin  [81-07-2] produced by the Sherwin-Williams process were nonmutagenic. The mutagenic activity of saccharin lot S-1469 was traced to a moderately polar chromatog. fraction representing impurities present in the saccharin at a level of <1.5 ppm, but was not attributable to a single component. In view of the low level of mutagenic activity observed and the low concentration of total impurities in Sherwin-Williams saccharin, the mutagenic material(s) are probably of no significance in animal feeding studies.

Food and Chemical Toxicology 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, Category: isothiazole.

Referemce:
https://en.wikipedia.org/wiki/Isothiazole,
Isothiazole – ScienceDirect.com

Tkachuk, Volodymyr’s team published research in Tetrahedron Letters in 60 | CAS: 7668-28-2

Tetrahedron Letters 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 C10H6INO3, Recommanded Product: 3-Aminobenzo[d]isothiazole 1,1-dioxide.

Tkachuk, Volodymyr published the artcileCyclic acyl amidines as unexpected C4-donors for fully substituted pyridine ring formation in the base mediated reaction with malononitrile, Recommanded Product: 3-Aminobenzo[d]isothiazole 1,1-dioxide, the publication is Tetrahedron Letters (2019), 60(30), 1959-1963, database is CAplus.

A new one-step, pseudo four-component approach for the synthesis of fully substituted pyridines via ring-opening of the cyclic acyl amidine of 3-amino-1H-isoindol-1-one and its aza-analogs during the reaction with malononitrile in the presence of sodium methoxide, followed by pyridine ring closure is reported. This method allows the one-step preparation of previously unknown 2-(pyridin-4-yl)(hetero)aryl carboxamides in good yields under mild reaction conditions.

Tetrahedron Letters 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 C10H6INO3, Recommanded Product: 3-Aminobenzo[d]isothiazole 1,1-dioxide.

Referemce:
https://en.wikipedia.org/wiki/Isothiazole,
Isothiazole – ScienceDirect.com

Jensen, Klaus G.’s team published research in Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie in 36B | CAS: 7668-28-2

Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische 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, Name: 3-Aminobenzo[d]isothiazole 1,1-dioxide.

Jensen, Klaus G. published the artcilePhosphoramides. XIX. Phosphorus pentoxide amine hydrochloride reagents in the synthesis of 3-amino-1,2-benzisothiazole 1,1-dioxides and 3-aminothieno[3,4-d]isothiazole 1,1-dioxides, Name: 3-Aminobenzo[d]isothiazole 1,1-dioxide, the publication is Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie (1981), 36B(12), 1640-3, database is CAplus.

Aminobenzisothiazole dioxides I (R = H, R1 = alkyl, cycloalkyl; RR1N = morpholino, piperidino) were prepared by heating saccharin and the hydrochlorides of primary and secondary aliphatic amines with P2O5 and N,N-dimethylcyclohexylamine at 240°. 3-Aminothienoisothiazole dioxides II (R2 = Pr, Me2CHCH2, EtCHMe) were similarly prepared from thieno[3,4-d]isothiazol-3(2H)-one 1,1-dioxide. In biol. screening against lymphocytic leukemia I were inactive.

Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische 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, Name: 3-Aminobenzo[d]isothiazole 1,1-dioxide.

Referemce:
https://en.wikipedia.org/wiki/Isothiazole,
Isothiazole – ScienceDirect.com

Schapira, Celia B.’s team published research in Journal of Heterocyclic Chemistry in 17 | CAS: 7668-28-2

Journal of Heterocyclic Chemistry 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, Application In Synthesis of 7668-28-2.

Schapira, Celia B. published the artcile3-Oxo-1,2-benzoisothiazoline-2-acetic acid 1,1-dioxide derivatives. I. Reaction of esters with alkoxides, Application In Synthesis of 7668-28-2, the publication is Journal of Heterocyclic Chemistry (1980), 17(6), 1281-8, database is CAplus.

Reaction of the benzisothiazolineacetic acids I (R = Me, Et, Me2CH, Me2CHCH2CH2, Ph) with alk. alkoxides was carried out under various conditions. Under mild conditions, o-(RO2C)C6H4SO2NHCH2COR (II) were obtained with good yields. Reaction of I or II with Na alkoxides under drastic conditions gave the esters III. Transesterification was observed when esters I were treated with NaOMe. Esters III were hydrolyzed in concentrated aqueous NaOH giving the acid III (R = H). Attempts to recrystallize III (R = H) from water resulted in its decarboxylation to give 2H-1,2-benzothiazin-4(3H)one 1,1-dioxide. III(R = H) could not be obtained by acid hydrolysis of esters III or by rearrangement of 3-oxo-1,2-benzoisothiazoline-2-acetic acid 1,1-dioxide. The rearrangement apparently took place by ethanolysis of the carboxamide linkage to the open sulfonamides (fast step) followed by a Dieckmann cyclization (slow step). Transesterification took place in the open sulfonamides.

Journal of Heterocyclic Chemistry 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, Application In Synthesis of 7668-28-2.

Referemce:
https://en.wikipedia.org/wiki/Isothiazole,
Isothiazole – ScienceDirect.com

Barr, C. R.’s team published research in Journal of the American Chemical Society in 73 | CAS: 7668-28-2

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.

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

Stoss, Peter’s team published research in Chemische Berichte in 108 | CAS: 7668-28-2

Chemische Berichte 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 C13H9FO2, Safety of 3-Aminobenzo[d]isothiazole 1,1-dioxide.

Stoss, Peter published the artcileCyclic sulfoximides. IV. 3-Imino-3H-1λ4,2-benzisothiazole 1-oxides, Safety of 3-Aminobenzo[d]isothiazole 1,1-dioxide, the publication is Chemische Berichte (1975), 108(12), 3855-63, database is CAplus.

2-Sulfinylbenzamides I (R = Me, Ph) cyclized with hydrazoic acid to yield benzisothiazole oxides II, which are cyclic sulfoximides. II reacted with BrCN or H2NCN, R2COCl [R2 = C6H4R3 (R3 = o-OH, m-OMe, o-OAc), OMe, OCHMeEt, OCH2CH2OMe, cyclohexyloxy, PPh, alkyl, CH2Ph, CH2OC6H4Cl-p, OEt], R4NCX (R4 = Ph, CH2CH2Cl, Bu, X = O; R4 = allyl, X = S), and N,N’-carbonyldiimidazole to give imino-N-substituted derivatives III, IV, V, and VI, resp.

Chemische Berichte 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 C13H9FO2, Safety of 3-Aminobenzo[d]isothiazole 1,1-dioxide.

Referemce:
https://en.wikipedia.org/wiki/Isothiazole,
Isothiazole – ScienceDirect.com