Month: November 2020

645-00-1, The chemical industry reduces the impact on the environment during synthesis 645-00-1, name is 1-Iodo-3-nitrobenzene, I believe this compound will play a more active role in future production and life.

General procedure: The mixture of nitroarenes (1.0 mmol), freshly prepared NaBH4(5.0 mmol), and 10 mL of EtOH/H2O (v/v 1:1) were added inSchlenk tube and stirred for 2 min at room temperature. Then, AgNPs(at)CMC-AG-Pct (1.5 mmol) was added in reaction media andstirred for designated time. The catalytic reduction studies were monitored using UVeVis spectroscopy. After the catalytic reductions,Ag NPs(at)CMC-AG-Pct was separated by centrifugationfrom reaction media, and the obtained filtrate was extracted withethyl acetate for three times and then dried over anhydrous magnesiumsulfate. Finally, organic solvent was evaporated to obtaindesired reduced products.

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

Reference:
Article; Baran, Talat; Journal of Molecular Structure; vol. 1182; (2019); p. 213 – 218;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The chemical industry reduces the impact on the environment during synthesis 627-32-7, name is 3-Iodo-1-propanol, I believe this compound will play a more active role in future production and life. 627-32-7

Example 31 Synthesis of OS-1-CA Conjugate 48 (FIG. 24) Compound 46 To a solution of oseltamivir carboxylic acid N-Boc derivative (64, 60 mg, 0.16 mmol) in MeOH (0.5 mL) was added KOH (6.87 mg, 0.17 mmol). The mixture was stirred at room temperature for 30 min, and then concentrated under reduced pressure. The residue was dissolved in DMF (0.5 mL), and then added 3-iodo-1-propanol (17 mL, 0.19 mmol). After stirring at 50 C. for 4 h, the mixture was evaporated under reduced pressure. The residues was dissolved in CH2Cl2 (10 mL) and extracted with 1 M HCl and brine, dried over MgSO4, concentrated under reduced pressure, and purified by flash silica gel column chromatography (EtOAc/hexane, 2:1) to afford compound 65 (50 mg, 72%). C22H38N2O7; white solid; mp 93-95 C.; TLC (EtOAc/n-hexane, 2:1) Rf=0.31; [alpha]D22=-81.9 (c=1.0, CH2Cl2); IR (film) 3309, 2964, 2935, 2878, 1686, 1536, 1458, 1392, 1368, 1295, 1255, 1172, 1057 cm; 1H NMR (400 MHz, CDCl3) delta 6.77 (1H, s), 5.88 (1H, d, J=8.8 Hz), 5.11 (1H, d, J=9.6 Hz), 4.28-4.31 (2H, m), 4.01-4.08 (1H, m), 3.95 (1H, d, J=7.2 Hz), 3.73-3.82 (1H, m), 3.70 (2H, t, J=6.0 Hz), 3.30-3.34 (1H, m), 2.72 (1H, dd, J=17.6, 5.2 Hz), 2.26 (1H, dd, J=18.0, 10.0 Hz), 1.97 (3H, s), 1.87-1.93 (2H, m), 1.47-1.57 (4H, m), 1.41 (9H, s), 0.85-0.91 (6H, m); 13C NMR (100 MHz, CDCl3) delta 170.9, 165.9, 156.2, 138.1, 128.8, 82.3, 79.5, 75.8, 61.8, 58.6, 54.6, 49.3, 31.5, 30.9, 28.4 (3*), 26.2, 25.7, 23.3, 9.7, 9.3; HRMS calcd for C22H39N2O7: 443.2757, found: m/z 443.2753 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 627-32-7. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Academia Sinica; Wong, Chi-Huey; Fang, Jim-Min; Liu, Kung-Cheng; Jan, Jia-Tsrong; Cheng, Yih-Shyun E.; Cheng, Ting-Jen R.; US2013/274229; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 610-97-9, name is Methyl 2-iodobenzoate, molecular formula is C8H7IO2, 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. 610-97-9

General procedure: To a solution of the corresponding aryl iodide (0.01 mol) in EtOAc (50 mL), activated Cu85 (2.5 g, 0.04 mol) was added and the solvent was removed under vacuum.? A reflux condenser was connected and the mixture was heated for 30 min at 205-220 C, under N2 atm, with stirring. The mixture was allowed to cool under N2 atm. EtOAc (100 mL) was added and the mixture was vigorously stirred at rt under N2 atm until a fine suspension was obtained. The suspension was filtered through a sintered glass pad and washed with EtOAc (250 mL, in portions) until absence of product (checked by TLC in the mother liquors). The solvent was removed under vacuum and the compound was purified by column chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 610-97-9, its application will become more common.

Reference:
Article; Sagrera, Gabriel; Bertucci, Ana; Vazquez, Alvaro; Seoane, Gustavo; Bioorganic and Medicinal Chemistry; vol. 19; 10; (2011); p. 3060 – 3073;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

18698-96-9, 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. 18698-96-9, name is 2-(2-Iodophenyl)acetic acid, A new synthetic method of this compound is introduced below.

2-lodophenylacetic acid (2.00 g, 7.63 mmol) was dissolved in dry THF (70 mL) and dry DMF (10 mL) under an atmosphere of nitrogen. To the solution were added 1 – hydroxybenzotriazole (1.134 g, 8.396 mmol) and EDCI (1 .609 g, 8.396 mmol) and /V,/V-diisopropylethylamine (5.318 mL, 30.53 mmol) and the reaction mixture was stirred at room temperature for 10 minutes. Ammonium carbonate (2.933 g, 30.53 mmol) was added in one portion, and the reaction was stirred room temperature for 7 hours. The volatiles were removed in vacuo and the residual solution was diluted with EtOAc (150 mL) and sat. aq. NaHC03 (100 mL). The layers were separated and the organic layer were washed with water (100 mL), brine (100 mL), dried (MgSO), filtered and concentrated in vacuo to give the title compound (138) (1.755 g, 88percent yield) as a beige solid; 1H NMR (400 MHz, cfe-DMSO) delta 7.82 (dd, J = 7.9, 0.9 Hz, 1 H), 7.42 (s, 1 H), 7.36 – 7.28 (m, 2H), 7.02 – 6.94 (m, 2H), 3.55 (s, 2H). LCMS Method C: Pi 4.77 min; m/z 262.0 [M+H]+.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LIMITED; HOLMES, Ian, Peter; BERGMAN, Ylva; LUNNISS, Gillian Elizabeth; NIKAC, Marica; CHOI, Neil; HEMLEY, Catherine Fae; WALKER, Scott Raymond; FOITZIK, Richard Charles; GANAME, Danny; LESSENE, Romina; WO2012/110773; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 766-99-4, name is 1-Ethynyl-4-iodobenzene, 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. 766-99-4

General procedure: A mixture of alkyne 1 (0.25 mmol), sodium sulfinate 2 (0.375 mmol), FeCl3 (20 mol %),K2S2O8 (20 mol %), and water (3 mL) was stirred at rt in an open flask for 6-9 h(Table 2). After completion of the reaction (monitored by TLC), the mixture was extracted with EtOAc (3 5 mL). The combined organic phases were dried over anhyd. Na2SO4, filtered, and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography using a mixture of EtOAc-n-hexane (1:4) as eluent to afford an analytically pure sample of beta-keto sulfones 3 (Table 2).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 766-99-4.

Reference:
Article; Singh, Atul K.; Chawla, Ruchi; Yadav, Lal Dhar S.; Tetrahedron Letters; vol. 55; 17; (2014); p. 2845 – 2848;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 19094-56-5, name is 2-Chloro-5-iodobenzoic acid, 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. 19094-56-5

General procedure: To a stirred suspension of 2-chloro-5-iodobenzoic acid(5.65 g, 0.02 mol) in CH2Cl2(20 mL) was added oxalylchloride(1.80 mL, 0.021 mol) and DMF(0.02 mL). Theresulting mixture was stirred for 4 h at room temperature.The mixture was concentrated, and the residual colorlesssolid was dissolved in CH2Cl2(40 mL). To this solutionwere added corresponding substituted benzene(0.02 mol)and then AlCl3(2.75 g, 0.021 mol) portionwise so that thetemperature did not exceed 0 C. After being stirred at 10-20 C for 3 h, the mixture was poured into ice water andextracted with CH2Cl2 three times. The combined organiclayers were washed with 1M HCl, water, and brine, thendried over MgSO4 and concentrated. The residual solid wascrystallized from ethanol to give as white solid.According to this procedure the following compoundswere prepared.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 19094-56-5.

Reference:
Article; Hu, Shengquan; Sun, Wuji; Wang, Yeming; Yan, Hong; Medicinal Chemistry Research; vol. 28; 4; (2019); p. 465 – 472;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 52548-14-8, name is 2-Iodo-5-methylbenzoic acid, 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 52548-14-8, 52548-14-8

The 2 H – 1, 2, 3 – triazole (3.45 g, 50 mmol), 2 – iodo -5 – methyl benzoic acid (5.24 g, 20 mmol), cesium carbonate (11.72 g, 36 mmol), trans – N, N’ – dimethyl – 1, 2 – diaminocyclohexane (0.51 g, 3.6 mmol), cuprous iodide (0.38 g, 2 mmol) and N, N – dimethyl formamide (30 ml) are added to the 100 ml round bottom flask in a single port, under the protection of nitrogen reaction solution gradually raising the temperature to 100 C reaction 4 hours. Stopping the reaction, cooling, liquid water (60 ml) diluted with water and ethyl acetate (200 ml ¡Á 2) extraction. The water layer is acidified to pH concentrated hydrochloric acid for 1 – 2, then adding ethyl acetate (200 ml ¡Á 2) extraction, the resulting organic layer dried with anhydrous sodium sulfate, filtered, filtrate turns on lathe does after separation and purification by column chromatography (dichloromethane/methanol (v/v)=50/1) to obtain the title compound (yellow solid, 2.76 g, 68%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Iodo-5-methylbenzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Zhang Yingjun; Xue Yaping; Lao Jinhua; Nie Biao; Xu Juan; (35 pag.)CN107759620; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 624-75-9 name is 2-Iodoacetonitrile, 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. 624-75-9

A 500-mL three-neck round-bottomed flask equipped with an addition funnel, thermometer and charged with 120a (6.70 g, 37.4 mmol), iodoacetonitrile (12.5 g, 74.9 mmol), iron (II) sulfate heptahydrate (5.20 g, 18.7 mmol) and dimethyl sulfoxide (250 mL). Hydrogen peroxide (35%, 18.2 g, 187 mmol) was added dropwise to the mixture over the period of 1 h through a syringe pump at room temperature using a water bath. Iron (II) sulfate heptahydrate (2 to 3 equivalent) was added to the reaction mixture in portions to keep the temperature between 25 C. to 35 C., until the color of the reaction mixture was deep red. When TLCs showed the reaction was not complete, more hydrogen peroxide (2-3 equivalent) and more iron (II) sulfate heptahydrate (1-2 equivalents) were added in the same manner until the reaction was complete. After that time, the reaction mixture was partitioned between saturated sodium bicarbonate solution (200 mL) and ethyl acetate (400 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (2*100 mL). The combined organic layers were washed with saturated sodium thiosulfate solution (50 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford a 78% yield (6.40 g) of 120b as a yellow oil: 1H NMR (500 MHz, CDCl3) delta 6.23 (s, 1H), 4.23 (s, 2H), 3.94 (t, 2H, J=6.5 Hz), 3.81 (s, 3H), 2.74 (t, 2H, J=6.5 Hz), 2.00 (m, 2H), 1.83 (m, 2H); (APCI+) m/z 219.3 (M+H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Iodoacetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Young, Wendy B.; US2013/116262; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

25252-00-0, Adding a certain compound to certain chemical reactions, such as: 25252-00-0, name is 2-Bromo-5-iodobenzoic acid, 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 25252-00-0.

General procedure: To a solution of 0.5 g compound 3(0.10 mol) in 3 ml DMF, 3.3 mg (0.01 mol) of copper iodide, 0.57 gcesium carbonate (0.1 mol), 20 mg (0.01 mol) Tetrakis (triphenylphosphine)palladium(0) was added under nitrogen atomophere. Then arylhalide (4-12) 0.11 mol was added under nitrogen atm, the mass wasstirred for 8 hrs at 75 C under nitrogen atm. Reaction was completed asindicated by TLC and the reaction mass was filtered through cellite bed,washed the bed with ethyl acetate (10 ml). The product layer (Ethylacetate layer)was then washed with water 10.0 ml, sodium bi sulphite10 ml followed by saturated sodium chloride solution (5.0 ml) and driedover (Na2SO4). The solvent was distilled off and the resulting productwas purified by column chromatography using ethyl acetate and nhexaneto get the pure product (4a-l). Yield observed was around85-90% for all the derivatives.

According to the analysis of related databases, 25252-00-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Thangarasu; Thamarai Selvi; Manikandan; Bioorganic Chemistry; vol. 81; (2018); p. 468 – 480;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-75-9,Some common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, molecular formula is C2H2IN, 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: Individual solutions of secondary N-alpha-trimethylsilylmethyl-N-benzylamines19 (5mmol) in acetonitrile (100mL) containing K2CO3 (10mmol) and 2-iodoacetonitrile (4.5mmol) were stirred for 12hat room temperature and concentrated in vacuo to give residues that were partitioned between water and CH2Cl2. The CH2Cl2 layers were dried and concentrated in vacuo to afford residues that were subjected to silica gel column chromatography (EtOAc/hexane=1: 15 – 1: 30) to yield corresponding alpha-aminonitiriles 11a18 (91%), 11b (74%), 11c (78%), 11d (85%), 11e (75%), 11f (75%), 11g (74%), 11h (75%), 11i (78%), 11j (78%) and 11k (66%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Iodoacetonitrile, its application will become more common.

Reference:
Article; Lim, Suk Hyun; Cho, Dae Won; Choi, Jungkweon; An, Hyunjun; Shim, Jun Ho; Mariano, Patrick S.; Tetrahedron; vol. 73; 44; (2017); p. 6249 – 6261;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com