Heterocyclic Building Blocks-Thiazolidine

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

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

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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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(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

With the rapid development of chemical substances, we look forward to future research findings about (S)-4-Benzylthiazolidine-2-thione

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Patent; RANBAXY LABORATORIES LIMITED; WO2008/23336; (2008); A2;,
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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

With the rapid development of chemical substances, we look forward to future research findings about Thiazolidin-2-one

Reference£º
Patent; Hoechst-Roussel Pharmaceuticals Inc.; US4933453; (1990); 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).

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

Reference£º
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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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

With the rapid development of chemical substances, we look forward to future research findings about 3-Aminorhodanine

Reference£º
Patent; Ciba-Geigy Corporation; US3996208; (1976); A;,
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As a common heterocyclic compound, it belongs to thiazolidine compound, name is 1,1-Dioxo-isothiazolidine, and cas is 5908-62-3, its synthesis route is as follows.,5908-62-3

Example 15 6-[(1,1-Dioxido-1,2-thiazolidin-2-yl)methyl]-1-(2-methoxyethyl)-5-methyl-3-(2-phenylethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione To a solution of 49 mul (0.668 mmol) of propane sultam in 1.5 ml of DMF were added 27 mg (0.668 mmol) of sodium hydride (60% suspension in mineral oil) and then the mixture was stirred at RT for 25 min (“Solution 1”). To a solution of 50 mg (0.134 mmol) of the compound from Ex. 138A in 1.3 ml of dichloromethane in another reaction vessel were added, at 0 C., 47 mul (0.267 mmol) of N,N-diisopropylethylamine and 10 mul (0.140 mmol) of thionyl chloride. After 20 min, one third of Solution 1 was added at 0 C. The reaction mixture was stirred at 0 C., with addition of a further third of Solution 1 after 20 min and after 40 min of reaction time. After the last addition, the cooling bath was removed and the reaction mixture was stirred at RT for about 18 h. All the volatile constituents were then removed on a rotary evaporator. The remaining residue was separated into its components by means of preparative HPLC (Method 8). After concentration of the product fractions and drying under high vacuum, 41 mg (64% of theory) of the title compound were obtained. 1H-NMR (400 MHz, CDCl3, delta/ppm): 7.41-7.16 (m, 5H, partially obscured by the CHCl3 signal), 4.30 (s, 2H), 4.25-4.17 (m, 2H), 4.11 (t, 2H), 3.70 (t, 2H), 3.35 (s, 3H), 3.26-3.15 (m, 4H), 2.99-2.88 (m, 2H), 2.50 (s, 3H), 2.44-2.28 (m, 2H). LC/MS (Method 1, ESIpos): Rt=1.03 min, m/z=478 [M+H]+.

5908-62-3 is used more and more widely, we look forward to future research findings about 1,1-Dioxo-isothiazolidine

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Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HAeRTER, Michael; KOSEMUND, Dirk; DELBECK, Martina; KALTHOF, Bernd; WASNAIRE, Pierre; SUessMEIER, Frank; LUSTIG, Klemens; (369 pag.)US2018/65981; (2018); A1;,
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26364-65-8, 2-Cyanoimino-1,3-thiazolidine is a thiazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,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.

As the paragraph descriping shows that 26364-65-8 is playing an increasingly important role.

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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.

General procedure: Compound 2 (100 mg, 0.5 mmol) and 2,4-thiazolidinedione or 2-thione-4-thiazolidinone derivatives (0.5 mmol) were dissolved in ethanol (5 mL). Piperidine (100 muL) was added as a catalyst and the reaction mixture was stirred at room temperature for 5 h. Then, the reaction mixture was poured into iced water to yield a precipitate. The product was filtered, washed with distilled water and recrystallized from the indicated solvents to yield compounds 3a-f., 1438-16-0

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Article; Anh, Hoang Le Tuan; Cuc, Nguyen Thi; Tai, Bui Huu; Yen, Pham Hai; Nhiem, Nguyen Xuan; Thao, Do Thi; Nam, Nguyen Hoai; Van Minh, Chau; Van Kiem, Phan; Kim, Young Ho; Molecules; vol. 20; 1; (2015); p. 1151 – 1160;,
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As a common heterocyclic compound, it belongs to thiazolidine compound, name is 1,1-Dioxo-isothiazolidine, and cas is 5908-62-3, its synthesis route is as follows.,5908-62-3

To a stirred solution of 5-{9-fluoro-6-methanesulfonyl-5-[(S)-oxan-4- yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-3-yl}-4-(2H3)methyl-l-methyl-lH-l,2,3- triazole (40.0 mg, 0.075 mmol) and isothiazolidine 1,1-dioxide (36.1 mg, 0.298 mmol) in NMP (0.40 mL) was added t-BuOK (29.2 mg, 0.261 mmol). This mixture was heated at 65 C for 2 h and cooled to room temperature. The mixture was purified via preparative LC/MS with the following conditions: Column: Waters XBridge Phenyl, 19 x 200 mm, 5- muiotaeta particles; Mobile Phase A: 5:95 ACN: water with 10 mM NH4OAC; Mobile Phase B: 95:5 ACN: water with 10 mM NH4OAC; Gradient: 15-70% B over 20 min, then a 5-min hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give 9.6 mg. (20%). NMR (500MHz, DMSO-de) delta 8.72 (s, IH), 8.38 (d, J=8.4 Hz, IH), 7.89 (s, IH), 7.62 (br d, J=8.1 Hz, 3H), 7.37 – 7.30 (m, 2H), 7.26 (s, IH), 6.82 (br d, J=10.4 Hz, IH), 4.11 (br s, 2H), 3.86 (br d, J=8.4 Hz, IH), 3.77 (s, 3H), 3.75 (s, 3H), 3.65 (br d, J=8.8 Hz, IH), 3.57 (br t, J=7.4 Hz, IH), 3.53 – 3.45 (m, IH), 3.40 (br d, J=12.1 Hz, IH), 3.19 (br t, J=11.6 Hz, IH), 2.62 (quin, J=7.1 Hz, 2H), 2.52 – 2.52 (m, IH), 1.95 (br d, J=12.5 Hz, IH), 1.77 – 1.58 (m, 2H), 0.43 (br d, J=12.5 Hz, IH); LCMS: RT = 1.573 min; (ES): m/z (M+H)+ = 638.05; LCMS: Column: Waters Acquity UPLC BEH CI 8, 2.1 x 50 mm, 1.7-muiotaeta particles; Mobile Phase A: 5:95 ACN:water with 10 mM LtOAc; Mobile Phase B: 95:5 ACN:water with 10 mM NH40Ac;Temperature: 50 C; Gradient: 0-100% B over 3 min, then a 0.75 min hold at 100% B; Flow: 1.11 mL/min. HPLC Purity 220nm: 99 %.

5908-62-3 is used more and more widely, we look forward to future research findings about 1,1-Dioxo-isothiazolidine

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Patent; BRISTOL-MYERS SQUIBB COMPANY; HAN, Wen-Ching; DEGNAN, Andrew P.; DESKUS, Jeffrey A.; GAVAI, Ashvinikumar V.; GILL, Patrice; SCHMITZ, William D.; STARRETT, John E., Jr.; (193 pag.)WO2016/183115; (2016); A1;,
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5908-62-3, 1,1-Dioxo-isothiazolidine is a thiazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,5908-62-3

A Schlenk tube was charged with 5-[5-({3-[(1 R,5S/1 S,5R)-1-(4-bromophenyl)-3- azabicyclo[3.1.0]hex-3-yl]propyl}thio)-4-methyl-4H-1 ,2,4-triazol-3-yl]-2-methylquinoline (cf. Example 2; 0.15 g), isothiazolidine 1 ,1 -dioxide (46 mg), tris(dibenzylideneacetone)- dipalladium(O) (6 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (10 mg), cesium carbonate (130 mg) and 1 ,4-dioxane (2 mL). The Schlenk tube was sealed with a teflon screwcap and the reaction mixture was stirred at 100 0C for 12 h. The reaction mixture was allowed to cool to room temperature, diluted with dichloromethane (10 mL), filtered EPO and concentrated in vacuo. The crude product was purified by flash chromatography (dichloromethane to 10% MeOH in dichloromethane) to give 50 mg of the free base of the title compound. To a solution of this material in dichloromethane (0.3 mL) was added HCI (0.087 mL, 1 M in Et2O), the solvent evaporated in vacuo and the material thus obtained triturated with Et2O to give 52 mg of the title compound as a white solid.NMR (1H, DMSO): delta 10.57 (bs,1 H), 8.27 (bd, 1 H), 8.19 (d, 1 H), 7.94 (t, 1 H), 7.82 (d, 1 H), 7.55 (d, 1 H)1 7.32 (d, 2H), 7.18 (d, 2H), 4.03 (dd, 1H), 3.72 (m, 3H), 3.60/3.20 (bm, 8H), 3.45 (s, 3H), 2.75 (s, 3H), 2.41 (m, 2H), 2.25 (m, 2H), 2.14 (m, 1 H), 1.66/1.10 (t/m, 2H). MS (ml z) 575 [MH]+.

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

Reference£º
Patent; GLAXO GROUP LIMITED; WO2007/22980; (2007); A1;,
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