Month: May 2021

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. 229178-74-9, name is 2,6-Difluoro-3-iodobenzoic acid, A new synthetic method of this compound is introduced below., SDS of cas: 229178-74-9

EXAMPLE 36A; Preparation of compound 2002; Step 1:; Sulfuric acid (3 mL) is added to a solution of 36a1 (15.0 g, 36.9 mmol) in MeOH (200 mL) and the resulting solution is stirred overnight at 800C. The mixture is cooled to RT, concentrated under reduced pressure, diluted with EtOAc (300 mL), washed with aqueous saturated sodium bicarbonate (3 x 100 mL), brine (100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford methyl ester 36a2.

The synthetic route of 229178-74-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; WO2009/76747; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 1031929-20-0, A common heterocyclic compound, 1031929-20-0, name is 4-Fluoro-2-iodobenzonitrile, molecular formula is C7H3FIN, 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: 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.

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; 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

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. 52914-23-5, name is 2-(4-Iodophenyl)ethanol, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-(4-Iodophenyl)ethanol

A suspension of (4-iodophenyl)ethanol (3.00 g, 12.09 mmol), ethynyltrimethylsilane (2.01 mL, 14.51 mmol), copper (_) iodide (115 mg, 0.60 mmol), bis(triphenylphosphine)palladium(II) dichloride (424 mg, 0.60 mmol), TEA (5.06 ml, 36.28 mmol) were stirred in THF (20 mL) at ambient temperature for overnight. The reaction solvent was evaporated under reduced pressure, and the residue was purified by column chromatography with hexane/ethyl acetate (5/1, v/v) to obtain the compound 54 (2.64 g, quant. yield): 1H NMR (400 MHz, CDCl3) _ 7.38 (d, J = 8.3 Hz, 2H), 7.08 (d, J = 8.2 Hz, 2H), 3.66 (td, J = 7.0, 3.9 Hz, 2H), 2.72 (t, J = 6.8 Hz, 2H), 0.25 (s, 9H); 13C NMR (100 MHz, CDCl3) _ 139.4, 132.0, 128.9, 121.0, 105.1, 93.7, 63.0, 38.9, 0.01.

According to the analysis of related databases, 52914-23-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; DALBY, Kevin N.; EDUPUGANTI, Ramakrishna; TALIAFERRO, Juliana; LEE, Juhyeon; (0 pag.)WO2018/160967; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

116632-14-5, name is 3-Iodonaphthalen-2-amine, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 3-Iodonaphthalen-2-amine

Compound (3-1) (3-iodonaphtalen-2-amine, 1.00 g, 3.72 mmol), copper iodide (0.21 g, 1.11 mmol), potassium carbonate (1.02 g, 7.44 mmol), and dimethylsulfoxide (DMSO, 37 ml) are put in a reaction vessel, after argon gas is substituted for gas therein, and then, stirred. Subsequently, Compound (3-2) (benzoylthiocyanate, 1.81 g, 11.15 mmol) is added thereto, and the obtained mixture is stirred at 90 C. for 12 hours. The resultant is cooled down to room temperature, water is added thereto, the obtained mixture is cooled down to room temperature, and water is added thereto, an organic layer is extracted therefrom with ethyl acetate and dried with anhydrous sodium sulfate, and a solvent therein is distilled under a reduced pressure and removed. A residue therefrom is purified through silica gel column chromatography (hexane:ethyl acetate in a volume ratio of 5:1) to obtain Compound (3-3) (N-(naphtho[2,3-d]thiazol-2-yl)benzamide, 0.60 g). This solid is dissolved in methanol (35 ml). Then, 10 ml of a 2N sodium hydroxide aqueous solution is added thereto, and the obtained mixture is heated and stirred for one night. Subsequently, 100 ml of water is added thereto, and a solid precipitate therein is filtered and obtained. The solid is twice washed with water (30 ml) and dried to obtain Compound (3-4) (naphtho[2,3-d]thiazole-2-amine(naphtho[2,3-d]thiazol-2-amine, 0.26 g, a yield of 35%).

The synthetic route of 116632-14-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung Electronics Co., Ltd.; Ishii, Norihito; Shibata, Katsunori; Ro, Takkyun; Kwon, Ohkyu; Kim, Sang Mo; Park, Kyung Bae; Yun, Sung Young; Leem, Dong-Seok; Lim, Youn Hee; Jin, Yong Wan; Choi, Yeong Suk; Choi, Jong Won; Choi, Taejin; Choi, Hyesung; Heo, Chul Joon; (50 pag.)US2019/51833; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 7212-28-4,Some common heterocyclic compound, 7212-28-4, name is 2-Iodo-N-phenylacetamide, molecular formula is C8H8INO, 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 mixture of DDPT (0.5 g), 6a-j (1.57 mmol) and K2CO3 (0.45 g, 3.26 mmol) in acetone (20 mL) was refluxed for 2 h. The reaction mixture was evaporated in vacuo, and purified by column chromatography (CH2Cl2: AcOEt = 32:1) to give compounds 7a-j. 1.6.1. 2-(4-Deoxyl-4′-demethylpodophyllotoxin-oxy)-N-phenylacetamide(7a)The title compound wasobtained in 44.6% yield as a white solid: mp 210-212 C; IR numax (cm-1) 3337,3040, 2962, 2909, 2878, 2842, 1767, 1690, 1597, 1537, 1504, 1483, 1462, 1443,1418, 1331, 1240, 1224, 1156, 1037, 932; 1H NMR (300 MHz, CDCl3)delta 9.58 (s, 1H, ArNH), 7.63 (d, J = 7.9Hz, 2H, ArH), 7.36 (t, J =7.8 Hz, 2H, ArH), 7.13 (t, J = 7.3Hz, 1H, ArH), 6.69 (s, 1H, ArH), 6.53 (s, 1H, ArH), 6.42 (s, 2H, ArH), 5.96 (d,J = 6.8 Hz, 2H, -OCH2O-), 4.64-4.62 (m, 3H, -OCH2CO-, CH), 4.59-4.35(m, 1H, -OCH2-), 4.11-3.74 (m, 1H, -OCH2-), 3.82 (s, 6H,2 ¡Á CH3), 3.12-3.07 (m, 1H, -CH2-), 2.84-2.76 (m, 3H,-CH-, -CH2-); ESI calcd. 516.2 [M – H]-, found 516.0 [M -H]-. HRMS calcd. C29H27NO8Na [M +Na]+ 540.1634, found 540.1646 (parts per million error of 2.2).

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

Reference:
Article; Zhu, Xiong; Fu, Junjie; Tang, Yan; Gao, Yuan; Zhang, Shijin; Guo, Qinglong; Bioorganic and Medicinal Chemistry Letters; vol. 26; 4; (2016); p. 1360 – 1364;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 41253-01-4, These common heterocyclic compound, 41253-01-4, name is 3-Nitro-5-iodobenzotrifluoride, 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.

Into a 50 mL round bottom flask was placed the 1-iodo- 3-nitro-5- (trifluoromethyl)benzene (1 g, 3.15 mmol) , N- methylpiperazine (0.379g, 3.78 mmol), bis(dibenzylideneacetone)palladium(0.029 g, 0.0315 mmol), sodium tert-butoxide (0.424 g, 4.416 mmol), 2-dicyclohexyl- 2′- (N,N-dimethylamino)biphenyl (0.037 g, 0.094 mmol) , and toluene (25 mL) . Reaction was heated to 800C with stirring for 20 hours. Reaction was cooled to room temperature and water (1 mL) and ethyl acetate (10 mL) were added. The organic layer is separated, concentrated under reduced pressure and purified via silica column eluting with 0 to 20% methanol in dichloromethane. The title compound was obtained as an orange oil.

The synthetic route of 41253-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2006/44823; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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 19393-94-3 as follows. Quality Control of 2,4-Dibromo-1-iodobenzene

Synthesis of Intermediate A2; Intermediate A1 (2.5 g, 6.9 mmoles), 1-pyreneboronic acid (1.7 g, 6.9 mmoles) and tetrakis(triphenylphosphine)palladium(0) (0.24 g, 0.21 mmoles, 3% Pd) were suspended in 1,2-dimethoxyethane (20 mL) under a nitrogen atmosphere, to which was then added a 2M sodium carbonate aqueous solution (2.2 g, 21 mmoles, 3 eq./10 mL), and the mixture was refluxed for 10 hours. Toluene (150 mL) and water (50 mL) were added to the reaction mixture, an organic layer was aliquoted, washed with saturated salt water (50 mL) and then dried over anhydrous magnesium sulfate, and the solvent was distilled off to obtain a pale yellow solid. This was purified by means of column chromatography (silica gel/hexane and 17% dichloromethane) to obtain a white solid (1.9 g, 63%). 1H-NMR (400 MHz, CDCl3, TMS): delta7.32 (1H, d, J = 8 Hz), 7.60 (1H, dd, J = 8 Hz, 2 Hz), 7.68 (1H, d, J = 9 Hz), 7.83 (1H, d, J = 8 Hz), 7.96 to 8.02 (3H, m), 8. 10 (2H, s), 8.16 (1H, d, J = 8 Hz), 8.20 (1H, d, J = 8 Hz), 8.21 (1H, d, J = 8 Hz)

According to the analysis of related databases, 19393-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2316816; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 52914-23-5, The chemical industry reduces the impact on the environment during synthesis 52914-23-5, name is 2-(4-Iodophenyl)ethanol, I believe this compound will play a more active role in future production and life.

(a) 104 g of p-iodophenethyl alcohol was combined in solution with 216 g of hydrobromic acid (48%) and 36 g of thiourea in 100 ml of water and reacted in accordance with the procedure outlined in Example I(a). Vacuum distillation at 91-95 and 0.2 mm Hg gave a 27% yield of p-iodophenethyl thiol having a refractive index of n25 D = 1.6411, an ALD of 0.56 ml/Kg and a formula of C8 H8 IS.

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-(4-Iodophenyl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Alcon Laboratories, Inc.; US4125554; (1978); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 14192-12-2, name is 2,5-Diiodobenzoic 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 14192-12-2, Product Details of 14192-12-2

Example 18 5-Chloro-N-((1-(2-methoxycarbonyl-4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide (29) To a solution of 2,5-diiodobenzoic acid (1.00 g, 2.67 mmol) in anhydrous MeOH (15 mL) cooled in an ice-bath, SOCl2 (0.50 mL, 6.85 mmol) was cautiously added (exothermal reaction). After the addition, the solution was heated at reflux overnight. It was then concentrated in vacuo to give methyl 2,5-diiodobenzoate (1.04 g).

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; Millennium Pharmaceuticals, Inc.; US2007/259924; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 1252046-13-1, 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. 1252046-13-1, name is 2-Bromo-5-iodobenzonitrile belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(¡À)-2-bromo-5-(1-hydroxybutyl)benzonitrile A round bottom flask was charged with the 2-bromo-5-iodobenzonitrile (2.00 g, 6.49 mmol) and THF (9 mL). Solution cooled down to -8 C. (ice/brine bath). Turbo Grignard 1.3M in THF (5.50 mL, 7.14 mmol) is then added in one portion and the reaction stirred for 15 minutes at -8 C. Butyraldehyde (0.698 muL, 7.79 mmol) is then charged in another flask and the preformed anion is added over the aldehyde/THF (4 mL) via canula and then, reaction allowed to warmed at room temperature overnight under magnetic stirring. Ammonium chloride (sat. aq.) added to the mixture. Extracted 3* with Ethyl Acetate. Combined organic layers washed with water (1*), with brine (1*), dried over sodium sulfate, filtered and concentrated to afford the crude material. Purification by silica gel flash chromatography (Ethyl Acetate/Heptane) provide the title compound as a yellow oil (1.33 g, 80.6%). 1H NMR (400 MHz, DMSO-d6) delta 0.83 (t, J=7.41 Hz, 3H) 1.18-1.34 (m, 2H) 1.46-1.57 (m, 2H) 4.52-4.58 (m, 1H) 5.37 (d, J=4.88 Hz, 1H) 7.56 (dd, J=8.58, 1.95 Hz, 1H) 7.79 (d, J=8.39 Hz, 1H) 7.81 (d, J=2.15 Hz, 1H); MS (M): 255.

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-Bromo-5-iodobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; US2012/165343; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com