Heterocyclic Building Blocks-Thiazolidine

The thiazolidine compound, cas is 5908-62-3 name is 1,1-Dioxo-isothiazolidine, mainly used in chemical industry, its synthesis route is as follows.

5908-62-3, A 50 ml flask was charged under nitrogen with 3-bromo-5-nitro-benzoic acid methyl ester (D11) (1 g, 3.8 mmol, 1 equiv), Cs2CO3 (536 mg, 4.4 mmol, 1.2 equiv) tris (DIBENZYLIDENEACETONE) DIPALLADIUM (0) (5 mg, 0.0055 mmol, 0.0154 equiv), Xantphos (10 mg, 0.014 mmol, 0.04 equiv) and toluene (15 ML). Isothiazolidine 1,1-dioxide (D22a) (536 mg, 4.4 mmol, 1.1 equiv) was then added and the resulting mixture was stirred at 90C for 16 hours then cooled to room temperature and diluted with H20 and AcOEt. The layers were separated, the aqueous phase diluted with a saturated aqueous NAHC03 solution and extracted with AcOEt. The combined organic phases were dried over MGS04 and concentrated in vacuo to give 3- (1, 1-DIOXO-116-ISOTHIAZOLIDIN-2-YL)-5-NITRO-BENZOIC acid methyl ester (D15) (187 mg, 16%) as a yellow solid. [M+H+NH3] + = 318.0, RT = 2. 81 min

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Reference£º
Patent; GLAXO GROUP LIMITED; WO2004/50619; (2004); A1;,
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The thiazolidine compound, cas is 26364-65-8 name is 2-Cyanoimino-1,3-thiazolidine, mainly used in chemical industry, its synthesis route is as follows.

General procedure: Thiazolidin-2-ylidene-cyanamide (0.317 g, 2.50 mmol) inacetonitrile (20 mL) was dropwise added to a stirred solutionof substituted benzyl bromide (2.5 mmol) and 14 mL NaOHaqueous solution (1 M). The mixture is stirred at room temperaturefor 8-10 h. The soild was collected by filtration,washed with n-hexane and dried in vacuo.

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Article; Jia, Ai-Quan; Ma, Sen; Wang, Jun-Ling; Zhang, Qian-Feng; Journal of Chemical Crystallography; (2020);,
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The thiazolidine compound, cas is 7025-19-6 name is 3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid, mainly used in chemical industry, its synthesis route is as follows.

7025-19-6, General procedure: 0.005 mol of appropriate rhodanine-3-alkanoicacid, 5 g molecular sieves 4 A, 25 cm3 isopropyl alcohol,0.0055 mol appropriate aldehyde and 2.53 g (0.025 mol)triethylamine were placed in a flask. The mixture washeated under a reflux condenser for 5 h in nitrogen. Afterheating, the solution was filtered hot. The permeate wascooled and 50 cm3 of 2M hydrochloric acid solution wasadded. The resulting sediment was filtered using Buechnerfunnel and crystallised from isopropyl alcohol or glacialacetic acid.

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Article; Tejchman, Waldemar; Korona-Glowniak, Izabela; Malm, Anna; Zylewski, Marek; Suder, Piotr; Medicinal Chemistry Research; vol. 26; 6; (2017); p. 1316 – 1324;,
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1438-16-0, 3-Aminorhodanine is a thiazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1438-16-0

General procedure: To a reaction vessel was added compound19(70 mg, 0.16 mmol), thiazolidine-2,5-dione (28 mg, 0.25 mmol), piperidine (2 muL, 0.02 mmol) and acetic acid (1 muL, 0.02 mmol) in the presence of toluene. The reaction mixture was refluxed overnight and the reaction solvent was removed by evaporation. The residual was dissolved in EtOAc and washed with H2O (2 x 10 mL) and brine. The organic layer was collected, dried over anhydrous Na2SO4, filtered, concentrated and purifiedby silica gel column chromatography using 20% EtOAc in hexanes to afford compound20(57 mg, 66%).

The synthetic route of 1438-16-0 has been constantly updated, and we look forward to future research findings.

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Article; Kim, Hyojin; Cho, Suk Joon; Yoo, Minjin; Kang, Seung Kyu; Kim, Kwang Rok; Lee, Hwan Hee; Song, Jin Sook; Rhee, Sang Dal; Jung, Won Hoon; Ahn, Jin Hee; Jung, Jae-Kyung; Jung, Kwan-Young; Bioorganic and Medicinal Chemistry Letters; vol. 27; 23; (2017); p. 5213 – 5220;,
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The thiazolidine compound, cas is 7025-19-6 name is 3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid, mainly used in chemical industry, its synthesis route is as follows.

7025-19-6, [00161] To a solution of 2,3-dimethoxybenzaldehyde 1 (200 mg, 1.20 mmol) and 3-(4- oxo-2-thioxothiazolidin-3-yl)propanoic acid 2 (247 mg, 1.20 mmol) in glacial acetic acid (4 mL) was added sodium acetate (197 mg, 2.41 mmol) and the reaction was heated at 90 C for 6 h. After the completion of reaction (as monitored by LCMS) the reaction mixture was poured into ice cooled water, stirred for 15 mm and the solid precipitated out was filtered, washed with diethyl ether and dried in vacuo to afford 235 mg (55% yield) of NADi-241 as yellow solid. ?H NMR (400 MHz, DMSO-d6) 12.50 (s, 1 H), 7.89 (s, 1 H), 7.25 (d, J = 1.87 Hz, 2 H), 7.06 (dd, J = 3.74, 5.62 Hz, 1 H), 4.20 – 4.26 (m, 2 H), 3.86 (s, 3 H), 3.82 (s, 3 H), 2.61 – 2.66 (m, 2 H) ; MS (ES+): mlz = 353.90 [M+Hj; HPLC = 99.28%.

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Patent; UNIVERSITY OF MIAMI; UNIVERSITY OF MARYLAND, BALTIMORE; SPYVEE, Mark; CAPOBIANCO, Anthony, J.; MACKERELL, Alex, Jr.; (114 pag.)WO2016/154255; (2016); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5908-62-3,1,1-Dioxo-isothiazolidine,as a common compound, the synthetic route is as follows.,5908-62-3

General procedure: Inside a N2 filled glovebox, benzenesulfonamide (250 mg, 1.590 mmol) and copper(I) iodide (15.14 mg, 0.080 mmol), 4-toluene bromide (326mg, 1.91 mmol), potassium carbonate (550 mg, 3.98 mmol), Acetonitrile (4 mL), and N1,N2dimethylethane-1,2-diamine (70.1 mg, 0.795 mmol) was charged into a vial. The vial was then heated to 70 oC for 8hr, LC indicated >97% conversion of benzenesulfonamide. The reaction mixture was then cooled to room temperature. 2N HCl (4mL) was added slowly, followed by EtOAc extraction (5mL x 3). The organic layers were combined, concentrated, and flash chromatographed (SiO2, 20:1–> 3:1 Heptane:EtOAc) to give N(p-tolyl) benzene sulfonamide as white solids (380 mg, 97%).

5908-62-3 1,1-Dioxo-isothiazolidine 642157, athiazolidine compound, is more and more widely used in various.

Reference£º
Article; Wang, Xiang; Guram, Anil; Ronk, Michael; Milne, Jacqueline E.; Tedrow, Jason S.; Faul, Margaret M.; Tetrahedron Letters; vol. 53; 1; (2012); p. 7 – 10;,
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3-Aminorhodanine, cas is 1438-16-0, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.

General procedure: A mixture of isothiocyanatobenzenesulfonamide 2 [32](0.01mol) and heterocyclic amine (0.01mol) in dioxane (30mL) containing triethylamine (0.1mL) was refluxed for 1h. The solvent was evaporated under reduced pressure and the solid obtained was filtered, washed with petroleum ether (bp 40-60C) and crystallized from ethanol to afford the thiourea derivatives.

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Article; Ghorab, Mostafa M.; Alsaid, Mansour S.; El-Gaby, Mohamed S.A.; Safwat, Nesreen A.; Elaasser, Mahmoud M.; Soliman, Aiten M.; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 299 – 310;,
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3-Aminorhodanine, cas is 1438-16-0, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.

General procedure: A mixture of aminorhodanine (1 mmol), isatin (1 mmol) and 5 muL of acetic acid in 2mL of distilled ethanol was placed in a cylindrical quartz reactor (Phi = 4 cm). The reactor was introducedinto a monomode microwave (Anton Paar) apparatus, for 5 min at100 C and 50 Watts. The crude reaction mixture was allowed tocool down at room temperature and ethanol (10 mL) or mixture of H2O/EtOH (10 mL) was directly added in the cylindrical quartzreactor. The resulting precipitated product was filtered off and waspurified by recrystallization from ethanol if necessary.

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Article; Khaldoun, Khadidja; Safer, Abdelmounaim; Boukabcha, Nourdine; Dege, Necmi; Ruchaud, Sandrine; Souab, Mohamed; Bach, Stephane; Chouaih, Abdelkader; Saidi-Besbes, Salima; Journal of Molecular Structure; vol. 1192; (2019); p. 82 – 90;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14446-47-0,Thiazolidine hydrochloride,as a common compound, the synthetic route is as follows.

N-t-Butyloxycarbonylglutamine (2.0 g, 8.12 mmol) was dissolved in THF (5 mL) and cooled TO-15C. CAIBE (ISOBUTYLCHLOROFORMATE) (1.06 mL, 8.12 mmol) and 4- METHYLMORPHOLINE (0.895 mL, 8.12 mmol) were added and the solution stirred for 15 min, The formation of the mixed anhydride was checked by TLC (eluent: CHCL3/MEOH : 9/1). After warming to-10C another equivalent of 4-methylmorpholine (0.895 mL, 8.12 mmol) and THIAZOLIDINEHYDROCHLORIDE (1.02 g, 8. 12 mmol) was added. The mixture was brought to room temperature and stirred overnight. The sediment FORMED was filtered off and the solvent was evaporated. The resulting oil was taken up in chloroform (20 ml) and washed with a saturated solution of sodium hydrogensulfate followed by a saturated solution of sodium bicarbonate, water and brine. The organic layer was separated, dried and evaporated. The resulting product was checked for purity by TLC (eluent: CHC13/MEOH : 9/1). Yield: 1.64 g. A portion of this product (640 mg) was dissolved in 3.1 mL ice cold HCl in dioxane (12.98 M, 20 equivalents) and left on ice. The progress of the reaction was monitored by TLC (eluent: CHCL3/MEOH : 9/1). After completion of the reaction the solvent was removed and the resulting residue was taken up in methanol and evaporated again. The resulting oil was dried over phosphorous-V-oxide and triturated twice with diethylether to give the title compound (0.265 g). The purity was checked by HPLC. The identity of the reaction product was checked by NMR analysis.

14446-47-0, As the paragraph descriping shows that 14446-47-0 is playing an increasingly important role.

Reference£º
Patent; PROSIDION LTD.; WO2005/20983; (2005); A2;,
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1,1-Dioxo-isothiazolidine, cas is 5908-62-3, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.

5908-62-3, To an oven dried 50 mE round-bottom flask, methyl2-bromo-5-methylbeioate (352 mg, 1.54 mmol), sultam(236 mg, 1.95 mmol), cesium carbonate (732 mg, 2.25mmol), palladium acetate (40.4 mg, 0.18 mmol), and Xanphos (136 mg, 0.23 5 mmol) were added and flask was placedunder argon. Reagents were suspended in 8 mE of anhydrousdioxane and mixture was heated at 100 C. overnight. Aftercooling to room temperature, reaction mixture was filtered,was1ng with ethyl acetate. Combined filtrate was concen446.04trated under reduced pressure and resulting film was purifiedby silica gel column chromatography (25-100% EthylAcetate in Hexanes) to yield intermediate 11.?H-NMR (DMSO, 400 MHz): oe 7.75 (d, 1H), 7.44 (m, 1H),7.35 (m, 1H), 3.89 (s, 3H), 3.81 (t, 2H), 3.28 (t, 2H), 2.55 (m,2H), 2.39 (s, 3H).ECMS m/z [M+H] C12H15N04S requires: 270.07. Found270.12.

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Reference£º
Patent; Gilead Sciences, Inc.; Sangi, Michael; (125 pag.)US9278975; (2016); B2;,
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