Month: August 2021

Reference of 83171-49-7,Some common heterocyclic compound, 83171-49-7, name is 3-Chloro-5-iodoaniline, molecular formula is C6H5ClIN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: The corresponding pyrazinoic acid (5.0 mmol) was dispersed in dry toluene (20 mL) and mixed with 1.5eq. of thionyl chloride (0.55 mL, 7.5 mmol). The reaction mixture was heated to reflux for approximately 1 h. Next, the excess of thionyl chloride was removed by repeated evaporation with dry toluene under vacuum.The crude acyl chloride was dissolved in dry acetone(20 mL) and added drop-wise to a stirred solution of the corresponding aniline (5.0 mmol) with triethylamine(5.0 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for up to 6 h. The completion of the reaction was monitored by TLC (eluent: hexane/ethyl acetate; r =2 : 1). The crude product adsorbed on silica gel by solvent evaporation was purified by flash chromatography(hexane/ethyl acetate gradient elution).The analytical data of the prepared compounds were fully consistent with the proposed structures and are available in the Supplementary Data.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-5-iodoaniline, its application will become more common.

Reference:
Article; Zitko, Jan; Barbora, Servusova-Vanaskova; Paterova, Pavla; Navratilova, Lucie; Trejtnar, Frantisek; Kunes, Jiri; Dolezal, Martin; Chemical Papers; vol. 70; 5; (2016); p. 649 – 657;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 19099-54-8, name is 1-Iodo-2-isopropylbenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Iodo-2-isopropylbenzene

General procedure: A DMF solution (8mL) of the o-substituted aryl iodide (0.36mmol), the o-bromobenzyl alcohol (0.36mmol) and norbornene (34mg, 0.36mmol) was added under nitrogen to a Schlenck-type flask, containing Pd(OAc)2 (4mg, 0.018mmol), the phosphine (0.036mmol), when required, and K2CO3 (124mg, 0.90mmol) or CsOPiv (211mg, 0.90). The reaction mixture was stirred at 105C for 24h. After cooling to room temperature the organic layer was diluted with EtOAc (20mL), washed twice with water (20mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the resulting residue was purified by flash chromatography on silica gel using mixtures of hexane-EtOAc as eluent.

The synthetic route of 19099-54-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Della Ca, Nicola; Fontana, Marco; Xu, Di; Cremaschi, Mirko; Lucentini, Riccardo; Zhou, Zhi-Ming; Catellani, Marta; Motti, Elena; Tetrahedron; vol. 71; 37; (2015); p. 6389 – 6401;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 17024-12-3, name is 9-Iodophenanthrene, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 17024-12-3, SDS of cas: 17024-12-3

A 500 mL three-necked round-bottomed flask equipped with a mechanical stirrer, reflux condenser, and inert gas in- and outlet was charged with quinidine (QD-1, 12.8g, 39.5 mmol, 1.2 eq). The flask was flushed for 30 min with a gentle stream of argon. Anhydrous dimethyl sulfoxide (130 mL, freshly distilled in presence of CaHz) was added, and the reaction mixture was stirred at room temperature until all the quinidine was dissolved. Sodium hydride (60% oil dispersion, 2.0g, 1.5 eq. ) was added in small portions yielding an orange, slightly cloudy solution of the corresponding sodium alkoxide. Upon addition of pyridine (6.4 mL, 2.4 eq. ) and copper (I) g, 1.2 eq. ) to the reaction mixture at room temperature, the color of the reaction mixture was changed from orange to dark green. After 30 min all of the precipitate dissolved, and a clear solution was formed. 9- iodophenanthrene (10.0 g, 32.9 mmol), was added, and the reaction mixture was kept at 113 C for 70 h (oil bath, temperature: 120 C). The reaction mixture was allowed to cool to room temperature. Water (100 mL), methylene chloride(100 mL), and diethyl ether (100 mL) were successively added to the brown solution followed by ethylenediaminetetraacetate disodium salt dehydrate (20 g) and concentrated aqueous ammonia solution (20 mL, 29%, w/w). The argon inlet was removed, and a gentle stream of air was flushed through the well-agitated reaction mixture for about 1 h. The reaction mixture was transferred to a separatory funnel and the turquoise blue aqueous phase separated from the dark brown organic phase. The aqueous layer was washed twice with methylene chloride (100 mL), and the combined organic phases were extracted three times with aqueous ammonia solution (200 mL, 5%, w/w) until the aqueous phase remained colorless. Then the organic layer was washed with HCl aq (1 N 2 x 50 mL) twice and washed with H20 three times (3 x 50 mL) to remove the left QD. The organic layer was washed with NH40H to neutralize the salt and dried over Na2S04 and the solvent was removed in vacuo to yield the crude product. The crude product was dissolved in ethyl ether (300 mL) and treated with HCI (IN in Et20) until no further precipitates was generated. The precipitates were collected and dissolved in CH2C12 and basified with NH40H and dried over Na2S04 and the solvent in vacuo to give yellowish foam QD-PHN (5.6g, 66% yield). [alpha]D23 = + 310.7(C 0.89 EtOH) (at)HNMR (CDC13, 400 Hz) 6 8.65-8.71 (m, 2H), 8.61 (d, J = 4.8 Hz, 1H), 8.52(d, J = 8 Hz, 1H), 8.07 (d, J= 9.2 Hz, 1H), 7.70-7.75 (m, 2H), 7.55 (d, 2.4 Hz, 1H), 7.38-7.46(m, 5H), 6.66 (s, 1H), 6.35 (br, 1H), 6.12-6.21 (m, 1H), 5.18(d, J=10.4 Hz, 1H), 5.12 (m, 1H), 4.03 (s, 3H), 3.32-3.42 (m, 2.97-3.06 (m, 2.79-2.87 (m, 1H),2.44-2.50(t, J= 10 Hz, 1H), 2.34-3.25 (m, 1H), 1.97 (br, 1H), 1.55-1.62 (m, 3H). ¹3CNMR:(CDCl3, 100Hz): 158.1, 150.4, 147.71, 144.7, 143.7, 140.3, 132.3, 132.2, 131.5, 127.5,127.3, 126.8, 126.7, 126.6,126.4, 124.5,122.8, 122.7,122.3, 121.8, 118.2, 114.7, 104.8, 100.8, 78.8, 60.5, 55.8, 50.2, 49.9, 39.6, 27.8, 26.5, 22.1. IR: 3062, 2935, 2863, 1622, 1594, 1507, 1454, 1226, 1117, 750.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BRANDEIS UNIVERSITY; WO2005/121137; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 3032-81-3, name is 1,3-Dichloro-5-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,3-Dichloro-5-iodobenzene

A mixture of D-methionine A (2.50 g, 16.8 mmol), 1 ,3-dichloro-5-iodo-benzene B (4.6 g, 17 mmol), copper(I) iodide (0.80 g, 4.2 mmol) and Cs2C03 (6.6 g, 20 mmol) in DMSO (20 mL) was heated at 90 °C for 23 h. To the reaction mixture was added 5percent citric acid until pH = 4, and then the mixture was extracted with EtOAc (3 x 50 mL), This crude was purified via column chromatography (gradient MeOH/CH2Cl2) to afford the desired product (2.59 g, 54percent yield) as an oil. A mixture of the methionine C and Mel (15 mL, 240 mmol) was stirred at 25 °C for 18 h, followed by adding TBME to form a precipitate which was filtered to afford a brown solid D (3.1 g, 42percent). .H NMR (400MHz ,DMSO-d6) delta = 6.72 (d, J = 2.0 Hz, 1 H), 6.65 (d, J = 2.0 Hz, 2 H), 4.33 – 4.15 (m, 1 H), 3.43 – 3.35 (m, 2 H), 2.89 (s, 3 H), 2.85 (s, 3 H); m/z 308 (M-128).

According to the analysis of related databases, 3032-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOGEN IDEC MA INC.; ERLANSON, Daniel, A.; MARCOTTE, Doug; KUMARAVEL, Gnanasambandam; FAN, Junfa; WANG, Deping; CUERVO, Julio, H.; SILVIAN, Laura; POWELL, Noel; BUI, Minna; HOPKINS, Brian, T.; TAVERAS, Art; GUAN, Bing; CONLON, Patrick; ZHONG, Min; JENKINS, Tracy, J.; SCOTT, Daniel; SUNESIS PHARMACEUTICALS, INC.; LUGOVSKOY, Alexey, A.; WO2011/29046; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 391211-97-5, name is 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid, A new synthetic method of this compound is introduced below., Product Details of 391211-97-5

A dry 100 mL round bottomed flask was charged with 3,4-difluoro-2-((2-fluoro-4- iodophenyl)amino)benzoic acid, (39) and 5 mL of DCM. The reaction mixture was cooled with an ice-bath to 0 C. 100 of anhydrous DMF was added followed by dropwise addition of neat oxalyl chloride (2 equiv.) over 5 min. The reaction was stirred at 23 C for 4 h. The solvent was then removed under reduced pressure. Excess oxalyl chloride was azeotropically removed with 2 X 5 mL portions of DCM under reduced pressure. The crude product was dissolved into 5 mL of DCM and the appropriate amine was added neat at 0 C. The ice bath was removed after 10 min and the reaction was permitted to warm to room temperature. The reaction was then stirred at 23 C for 6 h; completion of reaction was determined by TLC. A mixture of 10 mL of H20 and 10 mL of Et20 was added and the resultant mixture was extracted with Et20, washed with NaCl (aq, sat), and dried over Na2S04. The extract was decanted and then the solvent was removed under reduced pressure. The crude product was isolated on Si02 using hexane/EA.

The synthetic route of 391211-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE ADMINISTRATORS OF THE TULANE EDUCATIONAL FUND; DUQUESNE UNIVERSITY OF THE HOLY GHOST; CHAKRABARTY, Suravi; FLAHERTY, Patrick, T.; MONLISH, Darlene; CAVANAUGH, Jane, E.; BUROW, Matthew, E.; ELLIOTT, Steven; HOANG, Van, T.; WO2015/38743; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 608-28-6, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 608-28-6, name is 2-Iodo-1,3-dimethylbenzene, This compound has unique chemical properties. The synthetic route is as follows.

Add 0.2 mmol of potassium carbonate,0.005 mmol of tris (dibenzylideneacetone) dipalladium,1,3-bis (diphenylphosphine) propane 0.02mmol,18-crown-6-ether 0.1mmol,1,3-dimethyl-2-iodobenzene 0.1 mmol,1-methyl-4- (pent-1-yn-1-yl) benzene 0.25 mmol and1 mL of N, N-dimethylformamide was added to a 15 mL reaction tube,Fill it repeatedly with nitrogen 10 times, stir at room temperature for 15 min, add 0.5 mmol of water, and place in a reaction dish at 100 C for 16 h; cool to room temperature, dilute the reaction solution with ethyl acetateWash with water, dry the organic phase over anhydrous Na2SO4, filter, and concentrate.Purification by thin layer chromatography gave 13.4 mg of the target product as a colorless oil with a yield of 51%.

The chemical industry reduces the impact on the environment during synthesis 2-Iodo-1,3-dimethylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Huaqiao University; Cheng Guolin; Lv Weiwei; (12 pag.)CN110256184; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 73334-07-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 73334-07-3, name is N1,N3-Bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-methoxyacetamido)-N1-methylisophthalamide belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

280 g of iopromide-K2 from Example 1 is dissolved in 520 g of water. The solution is then pumped at a volumetric flow rate of 3 ml/minute through a flow pipe that is provided with a pressurization valve of 20 bar at 208-209 C. The flow pipe that is used has an inside diameter of 1.7526 mm and a heated length of 5.5 m (see FIG. 1). A solution of the isomerized iopromide secondary crystallizate is then purified via ion-exchange columns and crystallized from ethanol. The yield of the iopromide that is crystallized from ethanol is approximately 80% of the experiment relative to the secondary crystallizate that is used in the isomerization.

The synthetic route of N1,N3-Bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-methoxyacetamido)-N1-methylisophthalamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kagerer, Hartmut; Dembeck, Meike; Seba, Harmut; Ortmann, Ingo; US2007/265470; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 199786-58-8,Some common heterocyclic compound, 199786-58-8, name is (5-Bromo-2-iodophenyl)methanol, molecular formula is C7H6BrIO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a stirred mixture of (5-Bromo-2-iodo-phenyl)-m-ethanol (9.14 g, 29.2 mmol) in CH3Cl (150 mL) under argon was added 1M PBr3 in CH2Cl2 (35.0 mL, 35.0 mmol). The reaction mixture was stirred at room temperature for 20 min and then poured into a mixture of ice and saturated NaHCO3 solution (300 mL). The pH was adjusted to basic by addition of solid NaHCO3. This aqueous layer was extracted with EtOAc (1×600 mL, 2×400 mL). The combined EtOAc extracts were washed with brine (1×100 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give 4-bromo-2-bromomethyl-1-iodo-benzene (5.69 g, 52%). 1H NMR (CDCl3): delta 7.68 (d, 1H, J=8.80 Hz), 7.59 (s, 1H), 7.18 (d, 1H, J=8.80 Hz), 4.51 (s, 2H). HPLC: Rt=3.87 min.

The synthetic route of 199786-58-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fink, Brian E.; Gavai, Ashvinikumar V.; Vite, Gregory D.; Han, Wen-Ching; Misra, Raj N.; Xiao, Hai-Yun; Norris, Derek J.; Tokarski, John S.; US2005/250753; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 455-13-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 455-13-0 name is 4-Iodobenzotrifluoride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: A mixture of propargyl alcohol (1.0g, 18mmol), 1-Iodo-3-trifluoromethoxy-benzene (5.14g, 18mmol), copper iodide (0.342g, 1.8mmol), dichlorobis (triphenylphosphine) palladium (II) (0.632g, 0.9mmol), diethylamine (30ml) was degassed for 10min. and stirred for 20hat 25-25C. Excess of diethyl amine was distilled off under vacuum. The residue was diluted with water (50ml) and extracted with ethyl acetate (3×50ml). The organic layer was washed with brine solution and dried over Na2SO4. The solvent was evaporated and the crude product was purified by column chromatography (10% Ethyl acetate in hexane) to obtain pure 3-(3-Trifluoromethoxy-phenyl)-prop-2-yn-1-ol (3.8g, 100%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Iodobenzotrifluoride, and friends who are interested can also refer to it.

Reference:
Article; Basu, Sujay; Barawkar, Dinesh A.; Ramdas, Vidya; Patel, Meena; Waman, Yogesh; Panmand, Anil; Kumar, Santosh; Thorat, Sachin; Naykodi, Minakshi; Goswami, Arnab; Reddy, B. Srinivasa; Prasad, Vandna; Chaturvedi, Sandhya; Quraishi, Azfar; Menon, Suraj; Paliwal, Shalini; Kulkarni, Abhay; Karande, Vikas; Ghosh, Indraneel; Mustafa, Syed; De, Siddhartha; Jain, Vaibhav; Banerjee, Ena Ray; Rouduri, Sreekanth R.; Palle, Venkata P.; Chugh, Anita; Mookhtiar, Kasim A.; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 218 – 229;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 98-61-3, These common heterocyclic compound, 98-61-3, name is 4-Iodobenzenesulfonyl chloride, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A: Sulfonyl chloride (1 eq.) was dissolved in a mixture of dry DCM (0.2 M) and TEA (1.5 eq.). Amine (1.2 eq.) was added and the reaction was stirred at 20 C until completion (TLC). The solvent was removed under reduced pressure and the crude product was purified by column flash-chromatography on silica to give the sulfonamide.

Statistics shows that 4-Iodobenzenesulfonyl chloride is playing an increasingly important role. we look forward to future research findings about 98-61-3.

Reference:
Article; Heinrich, Daniel M.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Silva, Shevan; Rigoreau, Laurent J.M.; Trivier, Elisabeth; Raynham, Tony; Turnbull, Andrew P.; Denny, William A.; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 738 – 744;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com