Month: December 2020

1643-29-4, A common heterocyclic compound, 1643-29-4, name is 3-(4-Iodophenyl)propanoic acid, molecular formula is C9H9IO2, 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.

Next, the 4-iodohydrocinnamic acid is methylated. 350 g of the produced 4-iodohydrocinnamic acid is wet with 250 g water. To the mixture is added 1.4 L methanol and 1.5 g p-toluene sulfonic acid in water. The mixture is refluxed overnight, and excess methanol is removed. 500 mL toluene is added and mixed, and then excess toluene and water is removed. Next, 500 mL methanol is added to the mixture. The mixture is refluxed for 30 minutes, after which excess methanol is again removed. The result is 162 g of methyl-4-iodohydrocinnamic acid (61% purity).

The synthetic route of 1643-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XEROX CORPORATION; US2006/111582; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-75-9, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 624-75-9 as follows.

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), 4-acetylphenyl boronic 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): (93 mg, 75%); m.p. 156-157 C.; 1H NMR (CDCl3) delta 2.42 (s, 3H), 2.65 (s, 3H), 3.82 (s, 3H), 4.97 (s, 2H), 6.75 (s, 1H), 6.82 (s, 1H), 6.96 (s, 1H), 7.12 (d, J=4.9 Hz, 1H), 7.60 (s, 1H), 7.87 (d, J=8.1 Hz, 2H), 7.99-8.02 (m, 3H), 8.56 (d, J=5.1 Hz, 1H); 13C NMR (CDCl3) delta 21.60, 26.78, 37.78, 55.52, 112.34, 114.02, 116.86, 118.62, 119.33, 120.38, 122.67, 126.90, 128.76, 129.01, 137.12, 139.56, 140.61, 141.58, 141.96, 143.49, 150.20, 156.29, 160.54, 197.88.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 624-75-9, 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

The chemical industry reduces the impact on the environment during synthesis 624-75-9, name is 2-Iodoacetonitrile, I believe this compound will play a more active role in future production and life. 624-75-9

e) To a solution of 7-benzyloxymethyl-8-(4-hydroxyphenyl)-1,3-dipropyl-1,3,7-trihydropurine-2,6-dione (1 g, 2.2 mmol) in tetrahydrofuran (20 ml) was added potassium t-butoxide (0.28 g, 2.4 mmol), and the mixture stirred for 30 minutes at room temperature. Iodoacetonitrile (0.38 g, 2.23 mmol) was then added, and the mixture stirred for 16 hours at room temperature. The solvent was removed under reduced pressure, and the residue was dissolved in ethyl acetate and passed through a silica gel plug, to provide 7-benzyloxymethyl-8-(4-cyanomethoxyphenyl)-1,3-dipropyl-1,3,7-trihydropurine-2,6-dione, a compound of formula (7)

The chemical industry reduces the impact on the environment during synthesis 624-75-9. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Kalla, Rao; Perry, Thao; Elzein, Elfatih; Varkhedkar, Vaibhav; Li, Xiaofen; Ibrahim, Prabha; Palle, Venkata; Xiao, Dengming; Zablocki, Jeff; US2005/261316; (2005); A1;,
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. 18698-96-9, name is 2-(2-Iodophenyl)acetic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 18698-96-9

General procedure: Pd(OAc)2 (22.4 mg, 0.10 mmol, 0.1 equiv), Ph3P (57.6 mg, 0.22, 0.22 equiv), and Cs2CO3 (1.63 g, 5 mmol, 5 equiv) were added to a flamedried, sealable vial under argon. Dry, degassed MeCN or DMF (3 mL) was added and the yellow mixture was stirred under argon for approximately 5 min. Aryl iodide (1.00 mmol, 1 equiv), alkyl iodide (10.00 mmol, 10 equiv), and olefin (5.00 mmol, 5 equiv) were added successively to the reaction mixture under argon. The mixture was stirred for 5 min, then solid norbornene (470 mg, 5.00 mmol, 5 equiv) was added. After a final argon purge, the vial was capped and placed in an oil bath that had been preheated to 90 ¡ãC. After 4?10 h, the mixture was cooled to r.t. Reactions performed in MeCN were filtered over a short pad of Celite (eluting with CH2Cl2) and concentrated in vacuo. Reactions performed in DMF were diluted with EtOAc? hexanes (1:1) and washed with brine twice. After drying with MgSO4, the organic layer was filtered and concentrated. The crude products were purified by flash column chromatography (CH2Cl2?hexanes, 1:5, then Et2O?hexanes, 1:100?1:25).

The synthetic route of 18698-96-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qureshi, Zafar; Schlundt, Waldemar; Lautens, Mark; Synthesis; vol. 47; 16; (2015); p. 2446 – 2456;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

3032-81-3, 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. 3032-81-3, name is 1,3-Dichloro-5-iodobenzene, A new synthetic method of this compound is introduced below.

General procedure: A suspension of DL-5-methoxypyrrolidin-2-one (3a) or arylaminopyrrolidinones 3b,c (1 equiv), CuI (0.5 equiv), cesium carbonate (2 equiv), and corresponding aryl iodide (1 equiv) in dioxane was placed under a nitrogen atmosphere. The coupling ligand DMEDA (1 equiv) was added dropwise by using a syringe and the mixture was then stirred at 60 ¡ãC for various periods of time (14?88 h). At the end ofthe reaction, the insoluble salts deposited after cooling at r.t. were collected by filtration then washed with dichloromethane. The resulting filtrate was concentrated in vacuo and the residue was partitioned between water and dichloromethane. The organic layer was dried on MgSO4 and evaporated to dryness. The residue was finally purified by chromatography on silica gel column (EtOAc/n-heptane) to afford pure N-arylated compound 40?44.

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:
Article; Baudelet, Davy; Daich, Adam; Rigo, Benoit; Lipka, Emmanuelle; Gautret, Philippe; Homerin, Germain; Claverie, Christelle; Rousseau, Jolanta; Abuhaie, Cristina-Maria; Ghinet, Alina; Synthesis; vol. 48; 14; (2016); p. 2226 – 2244;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common compound: 135050-44-1, name is 3-Chloro-4-iodoaniline, 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. 135050-44-1

5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (21.15 g, 113.62 mmol) was added to 3-chloro-4-iodoaniline (24 g, 94.69 mmol) in EtOH (450 mL). The resulting solution was stirred at 80 C. overnight. The reaction mixture was filtered and the solid collected washed with diethyl ether (400 mL) to afford 5-[(3-chloro-4-iodoanilino)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione (37 g, 96%) as a white solid; 1H NMR (400 MHz, DMSO, 30 C.) 1.67 (6H, s), 7.34 (1H, dd), 7.90-7.98 (2H, m), 8.57 (1H, s), 11.20 (1H, s).

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, 135050-44-1, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; Kettle, Jason Grant; Bagal, Sharanjeet; Robb, Graeme Richard; Smith, James Michael; Goldberg, Frederick Woolf; Cassar, Doyle Joseph; Feron, James Lyman; US2019/177338; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

135050-44-1, Adding a certain compound to certain chemical reactions, such as: 135050-44-1, name is 3-Chloro-4-iodoaniline, 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 135050-44-1.

The N-(3-chloro-4-iodophenyl)methanesulphonamide used as a starting material was obtained by the reaction of 3-chloro-4-iodoaniline and methanesulphonyl chloride using a similar procedure to that described in the portion of Example 3 which is concerned with the preparation of N-(4-iodophenyl)methansulphonamide.

According to the analysis of related databases, 135050-44-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Imperial Chemical Industries PLC; ICI Pharma; US5236948; (1993); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common compound: 645-00-1, name is 1-Iodo-3-nitrobenzene, 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. 645-00-1

General procedure: A round bottom flask was charged with aryl halide (0.5 mmol) and terminal acetylene (0.6 mmol). To the mixture, Pd(OAc)2 (1 mol%), A4 (2 mol%) andK2CO3 (1.5 mmol) were added. The reaction mixture was stirred at roomtemperature in EtOH (4 mL) for the mentioned time. The formation of theproduct was confirmed by monitoring the TLC. The reaction mixture was thenextracted with ethyl acetate (3 10 mL). The extracted layer was dried overNa2SO4 and concentrated in rotary evaporator. The crude product was purifiedby column chromatography over silica gel (Eluent: n-hexane) to obtain thedesired product. The pure products were confirmed by 1H and 13C NMR.

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, 645-00-1, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Das, Sameeran Kumar; Sarmah, Manashi; Bora, Utpal; Tetrahedron Letters; vol. 58; 22; (2017); p. 2094 – 2097;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

82998-57-0, 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. 82998-57-0 name is 3-Iodo-4-methylbenzoic acid, 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.

3-Iodo-4-methylbenzoic acid (lOg, 38. 16mmol), bis (pinnacolato) diboron (14. 5g, 57. 24mmol), potassium acetate (18. 73g, 190.8mmol) and PdCl2dppf (3.12g, 3. 8mmol) in DMF (200ml) were heated at 80C for 21hrs. The solvent was evaporated from the cooled reaction under vacuum, the residue dissolved in ethyl acetate (300ml) and hydrochloric acid (2N, 300ml) and filtered through celite. The organic phase was separated and the aqueous extracted with ethyl acetate (2 x 300ml). The combined organic extracts were washed with brine (500ml) and dried (magnesium sulphate). The solvent was evaporated under vacuum and the residue absorbed onto silica and applied to a silica flash column. This was eluted with cyclohexane/ethyl acetate (5 : 1). The product fractions were concentrated under vacuum to give 4-methyl-3- (4, 4,5, 5-tetramethyl- [1, 3,2] dioxaborolan-2-yl) benzoic acid. LCMS: retention time 3. 65min. NMR : 8H [2H6]-DMSO 12.83, (1H, b), 8.23, (1H, d), 7.89, (1H, dd), 7.29, (1H, d), 2.51, (3H, s), 1.30, (12H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Iodo-4-methylbenzoic acid, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2003/93248; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

82998-57-0, The chemical industry reduces the impact on the environment during synthesis 82998-57-0, name is 3-Iodo-4-methylbenzoic acid, I believe this compound will play a more active role in future production and life.

General procedure: To mixture of compound N-(2-chloro-6-methylphenyl)-2-{[6-[4(1-piperazinyl)-2-methyl -4-pyrimidinyl]amino]-5-thiazolecarboxamide (6) (5.1 mol equivalent), the corresponding carboxylic acid (1:1 mol equivalents), DCC (1:1 molequivalents) and oxyma (1:1 mol equivalents) were charged into 4-necked round bottomed flask along with tetrahydrofuran.The slurry was slowly heated at 63-65 C for 4-5 h. Then cooled slowly to room temperature. The reaction mixture was quenched into demineralized water. The obtained solid was collected by vacuum filtration, washed with demineralized water. Suckdried thoroughly to afford crude product. The above obtainedcrude product was dissolved in hot dimethyl sulfoxide (DMSO) (5 volumes to compound weight) and charcoal treatment was given. The hot solution was slowly diluted with water (6 volumes to DMSO quantity) and cooled slowly to room temperature. The solid was colected by vacuum filtration and washed with 10 mL of demineralized water. Drying of the wet compound to get a white coloured product.

The chemical industry reduces the impact on the environment during synthesis 3-Iodo-4-methylbenzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Buchappa; Durgaprasad; Suneelkumar; Rani, P. Baby; Babu, K. Ravi; Rao, A. K. S. Bhujanga; Aparna; Asian Journal of Chemistry; vol. 28; 6; (2016); p. 1275 – 1280;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com