Month: October 2020

Adding some certain compound to certain chemical reactions, such as: 73334-07-3, name is N1,N3-Bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-methoxyacetamido)-N1-methylisophthalamide, 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 73334-07-3. 73334-07-3

12,000 g of iopromide, pure mother liquor (solid content about 6.2%), is concentrated by evaporation in a vacuum to form viscous oil of 892 g. 877 g of this residue is mixed in a suitable reaction vessel at a bath temperature of 65 C. with 439 ml of 1-propanol while being stirred. After inoculation with 0.73 g of iopromide, it is fully stirred for another 48 hours at a bath temperature of 65 C. The crystal suspension is then cooled to 20 C., stirred for I hour at this temperature and suctioned off via a suction filter. After washing with 4 portions of 110 ml of ethanol, the secondary crystallizate is dried at 40 C. in a vacuum-drying oven. Yield: 363.8 g (about 52% of the experiment)

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 N1,N3-Bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-methoxyacetamido)-N1-methylisophthalamide.

Reference:
Patent; Kagerer, Hartmut; Dembeck, Meike; Seba, Harmut; Ortmann, Ingo; US2007/265470; (2007); A1;,
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

The compound obtained in Example 21 (4.6 g, 15.35 mmol) and potassium carbonate (10.6 g, 76.73 mmol) were added to acetone (100 mL) and refluxed for 2 hours by heating. To this reaction mixture was dropwise added iodoacetonitrile (1.34 mL, 18.42 mmol), and refluxed over 2 hours. The acetone was removed by vacuum distillation, and to the residue were added water (200 mL) and ethyl acetate (200 mL). The organic layer was dried over anhydrous magnesium sulfate and distillated in a vacuum. The concentrate was subjected to column chromatography (silica gel, ethyl acetate-hexane 2:3 v/v) to afford a mixture of 2:1 of [4-(2-chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile and [4-(2-chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile as yellow oil. These two regioisomers (4.78 g, 92%) were used in the next reaction step without separation.[4-(2-Chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.29 (s, 3H), 3.71 (s, 3H), 5.19 (s, 2H), 6.73 (s, 1H), 6.75 (s, 1H), 6.85 (s, 1H), 7.06 (d, J=4.4 Hz, 1H), 7.26 (s, 1H), 7.79 (s, 1H), 8.24 (d, J=4.8 Hz, 1H); 13C NMR (CDCl3) delta 21.53, 39.97, 55.29, 110.91, 111.12, 113.65, 115.67, 118.75, 121.59, 121.65, 122.78, 130.58, 132.37, 140.16, 143.28, 149.68, 151.45, 151.79, 159.71, 162.33.[4-(2-Chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.39 (s, 3H), 3.83 (s, 3H), 4.94 (s, 2H), 6.63 (s, 1H), 6.74 (s, 1H), 6.92-6.96 (m, 2H), 7.19 (s, 1H), 7.93 (s, 1H), 8.17 (d, J=5.2 Hz, 1H); 13C NMR (CDCl3) delta 21.56, 37.78, 55.48, 112.15, 113.91, 117.08, 118.16, 119.88, 121.36, 122.48, 128.46, 139.57, 141.60, 142.19, 142.85, 149.78, 151.95, 160.48.To a solvent mixture of THF and water (4:1, 10 mL) were added the mixture prepared in Example 22 (320 mg, 0.95 mmol), 2-acetylphenylboronic acid (0.19 g, 1.13 mmol), dichlorobis(triphenylphosphine)palladium(II) (33 mg, 0.05 mmol) and potassium carbonate (131 mg, 0.95 mmol), and stirred at 70 C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled at room temperature, washed with ice water (100 mL) and extracted with ethyl acetate (100 mL¡Á3). The organic extract was dried over anhydrous magnesium sulfate and distilled under vacuum. The residue was subjected to prep-TLC using a solvent mixture of ethyl acetate/hexane to purify the desired products.Purification yield by prep-TLC (silica gel, ethyl acetate-hexane, 1:2, v/v): (152 mg, 61%); m.p. 63-64 C.; 1H NMR (CDCl3) delta 2.19 (s, 3H), 2.28 (s, 3H), 3.70 (s, 3H), 5.16 (s, 2H), 6.75 (s, 1H), 6.79 (s, 1H), 6.90 (s, 1H), 7.11 (d, J=4.1 Hz, 1H), 7.40-7.55 (m, 4H), 7.65 (dd, J=4.8, 7.2 Hz, 1H), 7.81 (s, 1H), 8.48 (d, J=5.1 Hz, 1H).

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; LEE, So Ha; Yoo, Kyung Ho; Oh, Chang Hyun; Han, Dong Keun; El-Deeb, Ibrahim Mustafa; Park, Byung Sun; Jung, Su Jin; US2011/15395; (2011); A1;,
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. 3032-81-3 name is 1,3-Dichloro-5-iodobenzene, 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. 3032-81-3

Step A Synthesis of 5-hydroxy-5-(3,5-dichlorophenyl)hexanenitrile as an intermediate The Grignard reagent of 3,5-dichlorophenyl iodide was prepared by the reaction of 20.0 grams (0.073 mole) of 3,5-dichlorophenyl iodide and 1.8 grams (0.073 mole) of magnesium turnings in 350 mL of diethyl ether. The reaction mixture was heated at reflux for about three hours and then allowed to cool to ambient temperature. To the Grignard reagent, with stirring, was added dropwise during a 15 minute period a solution of 8.4 mL (0.073 mole) of 5-oxohexanenitrile in 25 mL of diethyl ether. The exothermic reaction caused the reaction mixture temperature to rise to about 30¡ã C. Upon completion of addition, the reaction mixture was stirred for one hour and then was poured into 400 mL of water. The mixture was made acidic with about 80 mL of aqueous 2N hydrochloric acid and extracted with two 200 mL portions of diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chroma-tography on silica gel, using 5percent diethyl ether in methylene chloride as the eluant. The product-containing fractions were combined and concentrated under reduced pressure, yielding 8.4 grams of 5-hydroxy-5-(3,5-dichlorophenyl)hexanenitrile. The NMR spectrum was consistent with the proposed structure.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3032-81-3, and friends who are interested can also refer to it.

Reference:
Patent; FMC Corporation; US5521192; (1996); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

3058-39-7, 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. 3058-39-7, name is 4-Iodobenzonitrile, A new synthetic method of this compound is introduced below.

Example 3; Preparation of Organic Compound by Using Silicon-Based Cross-Coupling Reagents 1a to 1i of the Present Invention; The silicon-based cross-coupling reagents 1a to 1i of the present invention were used to carry out cross coupling reaction with an organic halide I-R10, thereby preparing various kinds of organic compounds. Table 1 shows reaction times, yields, a silicon-based cross-coupling reagent R1 used and an organic halide R10. Note that, in Table 1, product numbers correspond to the numbers of the following substances respectively.; Any one of the silicon-based cross-coupling reagents 1a to 1i (1.1 mmol) and the organic halide (1.0 mmol) were sequentially added to a mixture of K2CO3 (304 mg, 2.2 mmol), tri-2-furilic phosphine (4.6 mg, 20 mumol), and PdCl2 (1.8 mg, 10 mumol) in DMSO (2.5 mL), and the resulting mixture was stirred at 35¡ã C. When each of the times shown in Table 1 had passed, the resulting mixture was diluted with diethyl ether and was washed with water and brine, and then was dried over anhydrous MgSO4. After concentration under reduced pressure, the residue was purified by flash chromatography on silica gel, thereby obtaining organic compounds p1 to p24 which were cross-coupling products respectively corresponding to yields shown in Table 1. The following shows chemical formulas and characteristic data of the resultant organic compounds p1 to p22 and p24.

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; Nakao, Yoshiaki; Hiyama, Tamejiro; US2009/69577; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, A common compound: 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To a stirred solution of methyl 6-iodoanthranilate (53) (4.46 g, 16.1 mmol) in ethyl orthoformate (8.92 mL, 53.5 mmol) was added 2,2-dimethyl-1,3-dioxane-4,6-dione (1.16 g, 8.05 mmol). The mixture was stirred at 80 C for 45 min. After cooling to room temperature, the yellow precipitate was filtered and washed with ethanol (2 x 10 mL) to give methyl 2-[(2,2-dimethyl-4,6-dioxo[1,3]dioxan-5-ylidenemethyl)amino]-5-iodobenzoate (54) (3.31 g, 7.68 mmol) as a yellow solid. Yield 95%; mp 206-208 C; IR (KBr) nu 1198, 1227, 1251, 1284, 1429, 1585, 1607, 1685, 3100-3250 cm-1; 1HNMR (200 MHz, CDCl3) delta 1.07 (s, 6H, (CH3)2C), 3.98 (s, 3H, CH3O), 7.23 (d, 1H, J = 8.8 Hz), 7.86 (dd, 1H, J = 2.0, 8.8 Hz, H-3), 8.38 (d, 1H, J = 2.0 Hz, H-4), 8.65 (d, 1H, J = 14.0 Hz, C=CH-NH), 13.1 (d, 1H, J = 14.0 Hz, NH); 13C NMR (50 MHz, CDCl3) delta 27.2 ((CH3)2C), 53.2 (CH3O), 88.5 (C-5), 89.9 (C=CH-NH), 105.1 ((CH3)2C), 117.6 (C-3), 119.7 (C-1), 139.5 (C-2), 140.8 (C-6), 143.2 (C-4), 150.4 (C=CH-NH) 163.6 (CO), 164.0 (CO), 165.3 (CO); ESI-MS m/z 373.89 [M-CH3O-CO + H]+.

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, Methyl 2-amino-5-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Billaud, Emilie M.F.; Maisonial-Besset, Aurelie; Rbah-Vidal, Latifa; Vidal, Aurelien; Besse, Sophie; Bequignat, Jean-Baptiste; Decombat, Caroline; Degoul, Francoise; Audin, Laurent; Deloye, Jean-Bernard; Dolle, Frederic; Kuhnast, Bertrand; Madelmont, Jean-Claude; Tarrit, Sebastien; Galmier, Marie-Josephe; Borel, Michele; Auzeloux, Philippe; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 818 – 838;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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

To the solution of 2-bromo-5-iodo-benzoic acid (10 g, 31 mmol) in methanol (100 ml) was added thionyl chloride (5 ml, 68 mmol). The mixture was heated at 55C for 12 hours. The solvent and reagent were removed under reduced pressure and the mixture was diluted with EtOAc. The organic solution was washed with saturated sodium bicarbonate, water, and brine, and was dried with sodium sulfate. Concentration gave 2- bromo-5-iodo-benzoic acid methyl ester (10.5 g).

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 25252-00-0.

Reference:
Patent; GILEAD SCIENCES, INC.; GUO, Hongyan; KATO, Darryl; KIRSCHBERG, Thorsten, A.; LIU, Hongtao; LINK, John, O.; MITCHELL, Michael, L.; PARRISH, Jay, P.; SQUIRES, Neil; SUN, Jianyu; TAYLOR, James; BACON, Elizabeth, M.; CANALES, Eda; CHO, Aesop; KIM, Choung, U.; COTTELL, Jeromy, J.; DESAI, Manoj, C.; HALCOMB, Randall, L.; KRYGOWSKI, Evan, S.; LAZERWITH, Scott, E.; LIU, Qi; MACKMAN, Richard; PYUN, Hyung-Jung; SAUGIER, Joseph, H.; TRENKLE, James, D.; TSE, Winston, C.; VIVIAN, Randall, W.; SCHROEDER, Scott, D.; WATKINS, William, J.; XU, Lianhong; YANG, Zheng-Yu; KELLAR, Terry; SHENG, Xiaoning; CLARKE, Michael, O’Neil, Hanrahan; CHOU, Chien-hung; GRAUPE, Michael; JIN, Haolun; MCFADDEN, Ryan; MISH, Michael, R.; METOBO, Samuel, E.; PHILLIPS, Barton, W.; VENKATARAMANI, Chandrasekar; WO2010/132601; (2010); 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. 619-58-9, name is 4-Iodobenzoic acid, A new synthetic method of this compound is introduced below., 619-58-9

General procedure: A solution of 4-iodotoluene (1.05 g, 4.83 mmol) in a mix of 19.3 mL of n-Bu4NOH 1.5 M aqueous solution and 19.3 mL of DMSO (for an overall 0.125 M solution vs 4-iodotoluene) was prepared. Using Flow commander software, a continuous flow experiment was designed in order to control the flow stream of the pump matching 20 min of residence time (the flow stream was set at 0.50 mL/min). 37 mL of the reaction solution was injected (corresponding to 4.63 mmol of 4-iodotoluene that will be used to calculate the isolated yield; this method being used in order to maximise the reproducibility for the reported yield)using direct injection mode and the reagent stream was pumped into the 10 mL copper reactor (1.0 mm i.d.) at 150 C. 2 X 8 bar back pressure regulators (BPR) were placed in series atthe end of the reactor, allowing safe heating of the solvent. 48 mL of the crude reaction solution was then collected into 100 mL glass vial. A reconditioning, consisting of 3 mL of DMF followed by 3 mL of a 10% aqueous acetic acid solution, was run after the experiment in order to clean the reactor. The crude reaction solution was then acidified to pH = 1 with 2 N HCl. Water (150 mL) was added and the mixture was extracted with Et2O (3 X 150 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated under vacuum. The crude mixture was purified by automated flash column chromatography using a 24 g column and a 30-80% DCM/Hexanes gradient affording 406 mg of 2a (81% yield).

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:
Article; Cyr, Patrick; Charette, Andre B.; Synlett; vol. 25; 10; (2014); p. 1409 – 1412;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

351003-36-6, 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. 351003-36-6 name is 2-Fluoro-5-iodobenzonitrile, 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: Into an oven-dried flask equipped with a magnetic stir bar was added aryl fluoride (1.00 g, 1.0 eq.), Na2S (1.1 eq.) and DMF (5 mL) under argon. The reaction mixture was stirred at room temperature for 1 h. Then 1 M NaOH (50 mL) was added and was washed with CH2Cl2 (2 x 25 mL). The aqueous layer was acidified to pH ~ 1-2 with 6 N HCl and extracted with CH2Cl2 (2 x 50 mL). The combined organic layer was washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to provide a crude residue. To the residue was added 10% HCl (40 mL) and cooled with an ice-water bath. Then zinc dust (4 g) was added and the mixture was stirred for 1 h. Then EtOAc (100 mL) was added and the mixture was stirred for an additional 30 minutes. The organic layer was separated and washed with water (40 mL) and brine (40 mL), dried over MgSO4, filtered and concentrated to provide the desired product with satisfactory purity.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Fluoro-5-iodobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Taldone, Tony; Patel, Pallav D.; Patel, Hardik J.; Chiosis, Gabriela; Tetrahedron Letters; vol. 53; 20; (2012); p. 2548 – 2551;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 34683-73-3, name is 1-Chloro-6-iodohexane belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 34683-73-3

6-(3’4′-dibenzyloxyflavon-3-yl)-hexyltrimethylammoniumchloride (6g) 4b was alkylated using 1-chloro-6-iodohexane, employing the same method as described for 5d. The crude product was purified by column chromatography (CH2Cl2) to give 1.6 g (94%) 3-(6-chlorohexyloxy)-3′,4′-dibenzyloxyflavone. 1H NMR (CDCl3): delta 1.36 (m, 4H, CH2), 1.68 (m, 4H, CH2), 3.47 (t, 2H, J=6 Hz, CH2Cl), 3.99 (t, 2H, J=6 Hz, OCH2), 5.23 (s, 2H, OCH2Ph), 5.27 (s, 2H, OCH2Ph), 7.03 (d, 1H, J=8 Hz, C5’H), 7.25-7.5 (m, 12H, 2* OCH2Ph+C6H, C8H), 7.66 (dt, 1H, J=7 Hz, 2 Hz, C7H), 7.71 (dd, 1H, J=8 Hz, 1 Hz, C6’H), 7.80 (d, 1H, J=1 Hz, C2’H), 8.23 (dd, 1H, J=7 Hz, 2 Hz, CSH).

The synthetic route of 34683-73-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vereniging christelijk wetenschappelijk anderwijs; US2002/147353; (2002); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 74-88-4, name is Iodomethane, molecular formula is CH3I, 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. 74-88-4

EXAMPLE 29 Preparation of 6-methyl-1-[(3-iodo-4,5-dimethoxy-phenyl)methyl]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole STR79 To a stirred, cooled (0 C.) solution of iodovanillin (10.0 g, 35.96 mmol.) in dimethylformamide (50 mL) was added anhydrous potassium carbonate (20.0 g, 143.86 mmol.) followed by iodomethane (3.11 mL, 50.0 mmol.). The mixture was allowed to warm to ambient temperature and stir for 14H. The mixture was poured into diethyl ether (500 mL) and washed with water (3*150 mL). The organic phase was dried over MgSO4 and concentrated under reduced pressure to afford 3-iodo-4,5-dimethoxybenzaldehyde (9.5 g) as a yellow oil which solidified upon standing and was used without further purification. STR80

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 74-88-4, its application will become more common.

Reference:
Patent; Eli Lilly and Company; US5500431; (1996); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com