Tag: M.W:100-200

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: O-phenylenediamines (0.065 mol) was heated with N-aminorhodanine (0.065 mol) in xylene (50 ml) for 5 hours. The obtained residue was filtered and was crystallized from aqueous alcohol (charcoal). The obtained solid was recrystallized in ethanol. 2-mercaptobenzimidazole 3a Yield = 87 %; mp>250 C.1HNMR (DMSO-d6): 7.10 (m, 2Har); 7.27 (m, 2Har); 12.42 (s,NH).13CNMR (DMSO-d6): 119.43 (CH); 126.36 (CH); 138.82 (C); 167.12 (C=S). HRMS, m/z: 150(M), calcd for C7H6N2S: 150.02517, found: 150.0251.

1438-16-0 3-Aminorhodanine 74033, athiazolidine compound, is more and more widely used in various fields.

Reference£º
Article; El Kihel; Ait Sir; Jebbari; Ahbala; Guesmi; Bauchat; Oriental Journal of Chemistry; vol. 32; 4; (2016); p. 1765 – 1768;,
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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: General procedure for synthesis of N-substituted-rhodanine derivatives RhAs: To a solution of aldehydes (3a-3h, 1.0 equiv.) in ethanol (10 mL) was added slowly to the solution of 3-amino-2-thioxothiazolidin-4-one (2, 1.0 equiv.) in EtOH. The reaction mixture was stirred at room temperature without a catalyst for between 4 h and 12 h, and was monitored by TLC. After, the mixture product was recrystallized from EtOH. After recrystallization, N-substituted-rhodanine derivatives (RhAs) were obtained as follows., 1438-16-0

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Article; Bayindir; Caglayan, Cuneyt; Karaman, Muhammet; Guelcin, ?lhami; Bioorganic Chemistry; vol. 90; (2019);,
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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.

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., 26364-65-8

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Reference£º
Article; Jia, Ai-Quan; Ma, Sen; Wang, Jun-Ling; Zhang, Qian-Feng; Journal of Chemical Crystallography; (2020);,
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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.

Add 0.01 mol to a 250 mL three-necked flask5-chloromethyl-3-(2,6-difluorophenyl)-1,2,4-oxadiazole,0.01mol2-(cyanoimino)thiazolidine,80mL DMF, stirring reaction at 80 C for 4h, TLC detection reaction is completed,Add distilled water, suction filtration, and dryness.Obtained 2.57g of a white solid.The yield was 80%., 26364-65-8

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Reference£º
Patent; Qingdao University of Science and Technology; Xu Liangzhong; Sun Jianxin; Cui Huanqi; Wang Minghui; (8 pag.)CN109320471; (2019); A;,
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5908-62-3,1,1-Dioxo-isothiazolidine, cas is 5908-62-3, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.

To a stirred solution of KHMDS in THF (1 M, 0.410 ml_, 0.410 mmol) and THF (1 mL) at 0 C was added a solution of 1 , 1-dioxo-isothiazolidine (0.044 g, 0.35 mmol) in THF (0.5ml_). The reaction mixture was stirred for 30 minutes at 0 C and then 3-[4-(bromomethyl)-3-chloro-phenyl]-5- (trifluoromethyl)-1 ,2,4-oxadiazole (0.100 g, 0.293 mmol), prepared according to procedures described in example 1 using 3-chloro-4-methyl-benzonitrile as starting material, was added. The reaction mixture was stirred at 0C for 2 h. The reaction mixture was then quenched with water and warmed to RT. The mixture was extracted with ethyl acetate and the combined organic layers washed with brine, dried over MgSC , filtered and concentrated under reduce pressure. LC/MS (Method A) retention time = 1.07 minutes, 398 (M+OH)”. The mass observed only in the negative ionization and corresponded to that of a hydrated species.

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Patent; SYNGENTA PARTICIPATIONS AG; HOFFMAN, Thomas, James; STIERLI, Daniel; POULIOT, Martin; BEAUDEGNIES, Renaud; (96 pag.)WO2017/93348; (2017); 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

Example 26: (lR.25.7R.85f)-5-r7-(l.l-Dioxo-llambda6-isothiazolidin-2 -yl)-l.1- dioxo-l,4-dihydro-llambda6-benzori,2,41thiadiazin-3-yll-3-(4-fluoro-benzyl)-6-hydroxy-3- aza-tricvclor6.2.1.02’7lundec-5-en-4-one[00353] A reaction flask was charged with copper (I) iodide (8 mg, 0.042 mmol), sarcosine (N-methyl glycine) (9 mg, 0.1 mmol), isothiazolidine 1,1 -dioxide (204 mg, 1.685 mmol), (lR,25′,7R,85r)-3-(4-fluoro-benzyl)-6-hydroxy-5-(7-iodo-l,l- dioxo-l,4-dihydro-llambda6-benzo[l,2,4]thiadiazin-3-yl)-3-aza-tricyclo[6.2.1.02’7]undec-5- en-4-one (prepared as described in Example 19, 100 mg, 0.168 mmol) and potassium phosphate (179 mg, 0.842 mmol). The flask was degassed and backfilled with nitrogen, and then anhydrous NN-dimethylformamide (3 mL) was added. The resulting suspension was vigorously stirred at 100 0C for 17 h, and then allowed to cool to 25 0C. The mixture was diluted with ethyl acetate (30 mL) and washed with 1.0 M aqueous hydrochloric acid solution (2 x 20 mL) and saturated aqueous brine solution (40 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification by flash column chromatography (Teledyne Isco RediSep column; 1st column: 100% dichloromethane, 2n column: 5% hexanes in dichloromethane) to afford the desired product. The crude product was triturated with absolute ethanol (3 x) and dried in vacuo at 60 0C to afford the desired product, ( R,2S,1R, 8S>5 -[7-(1,I -dioxo- 1 lambda6-isothiazolidin-2-yl)- 1 , 1 -dioxo- 1 ,4-dihydro- 1 lambda6- benzo[l,2,4]thiadiazin-3-yl]-3-(4-fluoro-benzyl)-6-hydroxy-3-aza- tricyclo[6.2.1.02’7]undec-5-en-4-one (70 mg, 0.119 mmol, 71%), as a solid. 1H nuMR (400 MHz, DMSO-de) delta: 1.17 – 1.24 (2H, m), 1.40 – 1.61 (4H, m), 2.39 – 2.46 (2H, m), 2.51 – 2.54 (IH, m), 2.64 – 2.65 (IH, m), 3.03 – 3.05 (IH, m), 3.53 – 3.60 (3H, m), 3.83 (2H, t, J= 6.3 Hz), 4.43 (IH, d, J= 15.4 Hz), 4.97 (IH, d, J= 15.6 Hz), 7.15 (2H, t, J= 9.0 Hz), 7.32 – 7.35 (2H, m), 7.51 – 7.54 (2H, m), 7.62 (IH, d, J= 8.5 Hz). LC-MS (ESI) calcd for C27H27FN4O6S2 586.14, found 587.4 [M+H+].

The synthetic route of 5908-62-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ANADYS PHARMACEUTICALS, INC.; WO2008/124450; (2008); 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

Into a 4 mL vial was added isothiazolidine 1,1-dioxide (9.04 mg, 0.075 mmol) and (S)-6-chloro-3-(1-(4-chloropyrimidin-2-ylamino)ethyl)quinolin-2(1H)-one IV-1 (25 mg, 0.075 mmol) in DMF (250 muL). To this solution was added Cs2CO3 (48.6 mg, 0.149 mmol) and DIEA (26.1 muL, 0.149 mmol) and the reaction mixture was stirred at 110 C. for 1.5 hours. The mixture was then diluted with EtOAc and washed with brine (*2). The organic extract was dried over Na2SO4, filtered, and concentrated under reduced pressure to provide the crude product. This crude material was purified by column chromatography on a Biotage chromatography system (eluted with 0-100% EtOAc in hexanes) to afford the title compound (5.2 mg, 17% yield). 1H NMR (300 MHz, CDCl3): delta ppm 8.03 (br s, 1H), 7.93 (br s, 1H), 7.61 (br s, 1H), 7.41 (br d, J=8.50 Hz, 2H), 6.70 (br s, 1H), 5.42 (br s, 1H), 4.03 (br s, 1H), 3.83 (br s, 1H), 3.46 (m, 2H), 3.38 (m, 2H), 1.55-1.71 (m, 3H). LCMS (Method 1): Rt 2.02 min, m/z 419.89[M+H]+.

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

Reference£º
Patent; Forma Therapeutics, Inc.; Lin, Jian; Ericsson, Anna; Campbell, Ann-Marie; Gustafson, Gary; Wang, Zhongguo; Diebold, R Bruce; Ashwell, Susan; Lancia, JR., David R.; Caravella, Justin Andrew; Lu, Wei; (171 pag.)US2016/83365; (2016); A1;,
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A common heterocyclic compound, the thiazolidine compound, name is 1,1-Dioxo-isothiazolidine,cas is 5908-62-3, mainly used in chemical industry, its synthesis route is as follows.

5908-62-3, Step 2-1-(1,1-dioxo-isothiazolidin-2-ylmethyl)-3-benzyl-5-bromo-benzene (8B) A mixture of 8A (5 g, 14.7 mmol), 1,3-propanesultam (3.6 g, 29.7 mmol) and potassium carbonate (4.1 g, 29.7 mmol) in acetonitrile (60 mL) was refluxed overnight. The solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and brine. The organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatograph (ethyl acetate/hexanes) to give 8B as a white solid.

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Patent; Zhuang, Linghang; Wai, John S.; Payne, Linda S.; Young, Steven D.; Fisher, Thorsten E.; Embrey, Mark W.; Guare, James P..; US2005/10048; (2005); A1;,
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A common heterocyclic compound, the thiazolidine compound, name is 3-Aminorhodanine,cas is 1438-16-0, mainly used in chemical industry, its synthesis route is as follows.

General procedure: Two indole groups, 1H-indole-3-carbaldehyde (1) and 5-Bromo-1H-indole-3-carbaldehyde (2) (Sigma-Aldrich) were used as the primary core for insertion of the substituents 3-amino-2-thioxo-thiazolidin-4-one, 2-thioxo-thiazolidin-4-one, thiazolidin-2,4-dione and 2-thioxo-imidazolidin-4-one. The substituents were obtained commercially, except thiazolidin-2,4-dione that was synthesized in our laboratory according to the methodology of Brown [69].Prior to this reaction process, the groups 3a, 3b, 3c and 3d were solubilized in ethanol in the presence of morpholine and left stirring for 10 minutes at a temperature of 65 C. After this, indole nucleus (1 and 2) was added to the reaction system to obtain the final derivatives. Change of color was observed in all reactions after addition of indoles and precipitate formation 20min later. The reaction was monitored by thin layer chromatography (TLC) to check product formation and termination of the reaction. In general, the reaction lasted about 1h. As the reaction finished, the products were filtered and subjected to purification by successive washing with ethanol. The purity of the products was verified by 1H NMR, 13C NMR, mass spectroscopy and infrared.

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Reference£º
Article; Lafayette, Elizabeth Almeida; de Almeida, Sinara Monica Vitalino; Cavalcanti Santos, Renata Virginia; de Oliveira, Jamerson Ferreira; Amorim, Cezar Augusto da Cruz; da Silva, Rosali Maria Ferreira; Pitta, Maira Galdino da Rocha; Pitta, Ivan da Rocha; de Moura, Ricardo Olimpio; de Carvalho Junior, Luiz Bezerra; de Melo Rego, Moacyr Jesus Barreto; de Lima, Maria do Carmo Alves; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 511 – 522;,
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5908-62-3,1,1-Dioxo-isothiazolidine, cas is 5908-62-3, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.

1, 3-propanesultam (72 mg, 0.60 MMOL) in anhydrous DMF (3 mL) was added under N2 to 60 % NaH in mineral oil (36 mg, 0.90 MMOL). The mixture was stirred for 20 min, then the compound prepared in Preparative Example 196 (200 mg, 0.46 MMOL) was added. The mixture was stirred at 100 C for 30 min, the solvent was evaporated and the residue was purified by flash chromatography using EtOAc as eluent to yield colorless solid (150 mg, 63%). LCMS : M+=523.

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Reference£º
Patent; SCHERING CORPORATION; PHARMACOPEIA, INC.; WO2004/22561; (2004); A1;,
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