Category: thiazolidine

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO135,mainly used in chemical industry, its synthesis route is as follows.,1438-16-0

General procedure: A solution in absolute ethanol (30 mL/mmol) of the adequate aldehyde (1 equiv) and hydrazine (1 equiv) was heated under reflux for 5-18 h depending on the reactants. After cooling to room temperature, the precipitated solid was collected by filtration and dried under vacuum to afford the corresponding hydrazone. If no precipitate was observed, the reaction mixture was concentrated under reduced pressure. 4.2.26 (E)-3-(2-hydroxybenzylideneamino)-2-thioxothiazolidin-4-one (6g). 31 Yellow solid, yield: 52%, mp: 179-180 C. IR (neat) numax: 3038, 1727, 1716, 1615 cm-1. 1H NMR (300 MHz, DMSO-d6) delta: 4.32 (s, 2H); 6.34-7.01 (m, 2H); 7.47 (ddd, J = 1.8, 7.2, 8.3 Hz, 1H); 7.83 (dd, J = 1.7, 7.8 Hz, 1H); 8.96 (s, 1H); 10.68 (s, 1H). 13C NMR (75 MHz, DMSO-d6) delta: 34.6; 116.7; 117.6; 119.6; 128.5; 134.6; 158.6; 167.0; 197.0. HRMS (DCI, CH4) m/z calcd for C10H9N2O2S2 [M+H]+: 253.0105, found: 253.0106.

With the complex challenges of chemical substances, we look forward to future research findings about 3-Aminorhodanine,belong thiazolidine compound

Reference£º
Article; Vanucci-Bacque, Corinne; Carayon, Chantal; Bernis, Corinne; Camare, Caroline; Negre-Salvayre, Anne; Bedos-Belval, Florence; Baltas, Michel; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 4269 – 4276;,
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As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO346,mainly used in chemical industry, its synthesis route is as follows.,5908-62-3

Under a nitrogen atmosphere, a solution of 5-bromo-6-chloro-pyridine-2-carboxylic acid methyl ester (Example 9 c, 1 g, 4 mmol), isothiazolidine 1,1-dioxide (730 mg, 06 mmol), copper(I) iodide (150 mg, 0.8 mmol), 1,3-di(pyridin-2-yl)propane-1,3-dione (CAN 10198-89-7, 180 mg, 0.8 mmol) and potassium carbonate (1.1 g, 8 mmol) in DMF (20 mL) was reacted for 24 h at 110 C. The reaction mixture was poured into water, and extracted with ethyl acetate (3¡Á50 mL). The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by column chromatography (silica gel, 4 g, 10% ethyl acetate in petroleum ether) to yield the title compound (0.048 g, 1.6 mmol, 41.4%) as yellow solid; MS (EI): m/e=291.0 [M+H]+.

With the synthetic route has been constantly updated, we look forward to future research findings about 1,1-Dioxo-isothiazolidine,belong thiazolidine compound

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Patent; Bissantz, Caterina; Grether, Uwe; Hebeisen, Paul; Kimbara, Atsushi; Liu, Qingping; Nettekoven, Matthias; Prunotto, Marco; Roever, Stephan; Rogers-Evans, Mark; Schulz-Gasch, Tanja; Ullmer, Christoph; Wang, Zhiwei; Yang, Wulun; US2012/316147; (2012); A1;,
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Name is 1,1-Dioxo-isothiazolidine, as a common heterocyclic compound, it belongs to thiazolidine compound, and cas is 5908-62-3, its synthesis route is as follows.,5908-62-3

3-CYCLOBUTYL-7- [ (5-IODO-2-PYRIDINYL) OXY]-2, 3,4, 5-TETRAHYDRO-1H-3-BENZAZEPINE (E207) (200 mg, 0.48 MMOL), isothiazolidine 1,1-dioxide (116 mg, 0.96 MMOL), (Evans, Brian J.; Takahashi Doi, Joyce; Musker, W. Kenndh J. Org. Chem.; 55; 9; 1990; 2580-2586) potassium carbonate (238 mg, 1.73 MMOL), copper (I) iodide (27 mg, 0.14 MMOL) and N, N- dimethylethylenediamine (0.02 ml, 0.14 MMOL) were added together in dry dioxane (3 ml) and heated in a microwave reactor at 140 C for 20 minutes. The mixture was diluted with methanol and applied to a SCX column eluting with methanol and then a mixture of. 880 AMMONIA/METHANOL (1: 9). The basic fractions were combined and concentrated in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of. 880 ammonia: methanol : dichloromethane (0.5 : 4.5 : 95) to afford the title compound (145 mg); MS (ES+) M/E 414 [M+H] +.

With the complex challenges of chemical substances, we look forward to future research findings about 1,1-Dioxo-isothiazolidine

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Patent; GLAXO GROUP LIMITED; WO2004/56369; (2004); A1;,
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As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO238,mainly used in chemical industry, its synthesis route is as follows.,1438-16-0

RO was synthesized by adding 2.0mMmethenolic solution of 7-(diethylamino)-2-oxo-2H-chromene-3-carbaldehyde to an equimolar methenolic solution of 3-aminorhodanine and refluxing with constant stirring for threehours. A brick red solid was precipitated which was filtered andwashed with diethylether and finally dried under vacuum overanhydrous CaCl2. RO was characterized through various spectroscopictechniques like IR, 1HNMR spectral studies alongwith mass determination through HRMS.Spectroscopic Characterization Data: IR (cm-1): 3182,2973, 2927, 2869, 2852, 1747, 1701, 1614, 1596, 1571, 1516,1421, 1375, 1356, 1293, 1255, 1191, 1163, 1130, 1097, 1030,878, 823, 769, 674; 1HNMR in CDCl3: delta 1.25 (t, 6H, CH3, J =6.9 Hz), 3.46 (q, 4H, CH2, J = 6.7 Hz), 3.792 (s, 3H, OCH3),4.177 (s, 2H, CH2), 6.602 (s, 1H, Ar-H), 6.76 (d, 1H, Ar-H, J =8.4 Hz), 7.42 (d, 1H, Ar-H, J = 8.7 Hz), 8.074, (s, 1H, Ar-H),8.325 (s, 1H, CH=N), 10.157 (s, 1H, NH); HRMS: m/z calculatedfor [C18H21N3O4S2Na]+ = 430.0871; found = 430.0888.

With the complex challenges of chemical substances, we look forward to future research findings about 3-Aminorhodanine,belong thiazolidine compound

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Article; Kumar, Virendra; Kumar, Ajit; Diwan, Uzra; Singh, Manish Kumar; Upadhyay; Bulletin of the Chemical Society of Japan; vol. 89; 7; (2016); p. 754 – 761;,
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Name is 2-Cyanoimino-1,3-thiazolidine, as a common heterocyclic compound, it belongs to thiazolidine compound, and cas is 26364-65-8, its synthesis route is as follows.,26364-65-8

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.

With the complex challenges of chemical substances, we look forward to future research findings about 2-Cyanoimino-1,3-thiazolidine

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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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3-Aminorhodanine, cas is 1438-16-0, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.

EXAMPLE 30 A solution of rhodanine-3-carbamoylsulphonyl chloride which is obtained if a solution of 3.11 g of 3-aminorhodanine in 50 ml of acetonitrile is added to a solution of 1.8 ml of chlorosulphonylisocyanate in 50 ml acetonitrile and the mixture is stirred for 40 minutes at 25 C, is reacted, analogously to Example 5, with a silyl ester solution as in Example 5 (approx. 1.5 mmols of silyl ester), and worked up. The resulting crude product, in acetone solution, is decolourised with active charcoal and then converted by means of sodium alpha-ethylhexanoate into the sodium salt of 6-[D-alpha-(rhodanine-3-carbamylsulphamylamino)-phenylacetamido]-penicillanic acid. In a thin layer chromatogram on silica gel, Rf52 = 0.56; Rf96 = 0.76; Rf100 = 0.20; Rf110 = 0.28. [alpha]D20 = + 110 +- 1 (c = 1 in 0.5 N NaHCO3)., 1438-16-0

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Patent; Ciba-Geigy Corporation; US3996208; (1976); A;,
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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

100 mg (0.231 mmol) of (¡À)-1-(4-bromophenyl)-7,8-dimethoxy-N,4-dimethyl-4,5-dihydro-3H-2,3-benzodiazepine-3-carboxamide (Example 49A), 33.6 mg (0.278 mmol) of 1,2-thiazolidine 1,1-dioxide (CAS [5908-62-3]), 64 mg (0.46 mmol) of potassium carbonate and 13 mg (0.023 mmol) of allylchloropalladium dimer (CAS [12012-95-2]) are charged in 3 ml of 2-methyltetrahydrofuran and the suspension is degassed with argon for 10 min. Then 39 mg (0.093 mmol) of di-tert-butyl(2?,4?,6?-triisopropylbiphenyl-2-yl)phosphane (CAS [564483-19-8]) are added, degassing with argon is carried out again, and the mixture is heated at 80 C. for 16 h. The crude mixture is filtered, and then the solvent is removed and the residue obtained is purified by preparative HPLC. This gave 32 mg (29% of theory) of the desired product as a solid. [2172] LCMS (Method 5): Rt=0.90 min; m/z=473 (M+H)+ [2173] 1H-NMR (300 MHz, CDCl3): delta=1.04 (d, 3H), 2.61 (pent, 2H), 2.83 (dd, 1H), 2.91 (d, 3H), 3.09 (dd, 1H), 3.46 (t, 2H), 3.70 (s, 3H), 3.87 (t, 2H), 3.96 (s, 3H), 5.37-5.50 (m, 1H), 6.42 (q, 1H), 6.62 (s, 1H), 6.75 (s, 1H), 7.30 (d, 2H), 7.55 (d, 2H).

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Patent; BAYER PHARMA AKTIENGESELLSCHAFT; Siegel, Stephan; Baeurle, Stefan; Cleve, Arwed; Haendler, Bernard; Fernandiez-Montalvan, Amaury Ernesto; Moenning, Ursula; Krause, Sabine; Lejeune, Pascale; Schmees, Norbert; Busemann, Matthias; Holton, Simon; Kuhnke, Joachim; US2015/203483; (2015); A1;,
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Thiazolidin-2-one, cas is 2682-49-7, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.

EXAMPLE 6 3-(4-Bromobutyl)-2,2-dimethyl-4-thiazolidinone A solution of 2,2-dimethyl-4-thiazolidinone (5.00 g) in DMF (30 ml) was added dropwise to a suspension of NaH (0.0419 mole, previously washed with hexane) in DMF (30 ml) under N2. The resultant mixture was stirred for 1 h, transferred to an addition funnel and added dropwise to a solution of 1,4-dibromobutane (18.10 g) in DMF (50 ml) over a period of 40 min. The resultant solution was heated at 70 C. under N2 for 120 hr. TLC analysis (silica gel, 10% EtOAc/CH2 Cl2) showed the presence of one major product and starting thiazolidinone. The reaction mixture was cooled to room temperature and poured into H2 O (400 ml), and the aqueous mixture extracted with EtOAc (3*175 ml). The combined extracts were washed with H2 O (200 ml) and brine (200 ml), dried over Na2 SO4, and concentrated in vacuo to an oily residue (20.44 g). The crude product was purified by HPLC (4% EtOAc/CH2 Cl2) to yield 5.91 g of oil. Distillation in vacuo afforded 4.61 g of a faint yellowish oil, bp 133-136 C./0.70 mm Hg. ANALYSIS: Calculated for C9 H16 BrNOS: 40.60% C; 6.06% H; 5.26% N. Found: 40.63% C; 6.03% H; 5.17% N., 2682-49-7

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Patent; Hoechst-Roussel Pharmaceuticals Inc.; US4933453; (1990); A;,
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(S)-4-Benzylthiazolidine-2-thione, cas is 171877-39-7, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.

To a solution (45r)-4-benzyl-l,3-thiazolidine-2-thione (38 g) in dichloromethane (350 mL), cooled to O0C was added propylene oxide (12.7 mL) and trifluoroacetic acid (14 mL). After stirring the reaction mixture for 2 hours, the solvents were evaporated under reduced pressure to obtain a residue which was purified by column chromatography over silica gel using 20% ethylacetate in hexane as eluant to afford the title compound (0.9 g). Mass (m/z): 194.18, 171877-39-7

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Patent; RANBAXY LABORATORIES LIMITED; WO2008/23336; (2008); A2;,
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2-Cyanoimino-1,3-thiazolidine, cas is 26364-65-8, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.

In a dry 50 mL single-mouth flask, 10 mmol of 2-cyanoimino-1,3-thiazolidine and 5 mL of acetone were added.In an ice bath, 0.32 mL of a 50% aqueous solution of NaOH was added, and the temperature was controlled at 0C to 5C.Add dropwise a solution of 5-(2,4-difluorophenyl)-2-furanoyl chloride in acetone to control the rate ofThe temperature was kept at 0C-5C; after the addition was completed, the reaction was performed at 0C-5C for 1-2 hours and TLC test.After the reaction is completed, a 4mol/L hydrochloric acid solution is added to adjust the pH to neutrality.Dichloromethane extraction was added and the dichloromethane layer was successively saturated with sodium bicarbonate,Saturated brine and water were washed three times. The dichloromethane layer was dried over anhydrous magnesium sulfate and filtered.The compound was isolated using a silica gel column (eluent: a 2:1 volume ratio of petroleum ether to ethyl acetate).Yield 75%, 26364-65-8

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Patent; South China Agricultural University; Cui Zining; Xiang Xuwen; Tao Hui; Jiang Shan; Zhang Lianhui; (19 pag.)CN107674070; (2018); A;,
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