Month: June 2021

Electric Literature of 76801-93-9, 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. 76801-93-9, name is 5-Amino-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1Ten experiments were made, each of which used two parallel crystallisers (reactors A and B) where one had mother liquor distilled off and one had not. The solutions of crude Compound A were in all cases made the following way.Compound B was acetylated by a mixture of acetic anhydride and acetic acid (concentration about 91 v/v %, 2.0 L/kg Compound B) at 50-125 C. in the presence of catalytic amounts of p-toluene sulphonic acid. Excess acetic anhydride and acetic acid were distilled off under reduced pressure, and the resulting viscous solution diluted with methanol and water and hydrolysed by addition of aqueous sodium hydroxide at 50-60 C. to a stable pH of about 12. Hydrochloric acid (17.5 w/w %) was added to a pH of about 10.5-11.5 at 60 C. Then, seeds of crystalline Compound A (0.004 kg/kg Compound B) were added, and pH was further adjusted to 6.5-7.5 by hydrochloric acid (17.5 w/w %). At this stage the solvent composition was approximately 25% methanol and 75% water, with a total mother liquor volume of about 3.8 L/kg Compound A.In reactor A of each experiment a certain fraction of the mother liquor volume was removed by distillation, either at atmospheric or reduced pressure (95-100 C. at atmospheric pressure, 55-60 C. under reduced pressure). In reactor B nothing was distilled off. The content of both reactors were then allowed to cool gradually to 15 C. over 10-12 hours before filtration, wash with methanol and drying under reduced pressure and elevated temperature. The purity of the crystals was measured by HPLC. The following results were obtained: Water Reduction Water Reduction Isolated content in of mother content in of mother yield mother Compound liquor mother Compound liquor increase, liquor, B purity, volume, liquor, B purity, volume, reactor B vs. reactor A reactor A reactor A reactor B reactor B reactor B reactor A 1 81% 99.6% 11% 76% 99.6% None 1.3% 2 84% 99.6% 11% 76% 99.6% None 1.4% 3 85% 99.5% 14% 78% 99.5% None 1.7% 4 84% 99.5% 17% 73% 99.6% None 1.9% 5 83% 99.5% 14% 75% 99.5% None 1.6% 6 88% 99.5% 27% 77% 99.4% None 2.9% 7 91% 99.5% 24% 80% 99.5% None 2.5% 8 89% 99.5% 36% 76% 99.5% None 2.9% 9 85% 99.4% 28% 74% 99.5% None 2.4% 10 89% 99.4% 32% 75% 99.5% None 3.1%

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, 5-Amino-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GE HealthCare AS; US7754920; (2010); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 64248-58-4, A common heterocyclic compound, 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, molecular formula is C6H3F2I, 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.

To a solution of compound 33b, 4-Methyl-2-(5-piperidin-3-yl-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester (110 mg, 0.25 mmol) in dimethylsulfoxide (0.2 ml) was added L-proline (4.4 mg, 0.04 mmol), potassium carbonate (52.5 mg, 0.38 mmol), and copper iodine (3.6 mg, 0.02 mmol). The reaction was degassed under nitrogen and 1,2-difluoro-4-iodobenzene (45.4 mg, 0.19 mmol), was added, the reaction was again degassed and then heated to 90 C. The reaction was stirred over 48 hours. The reaction was partitioned between EtOAc/H2O, washed with H2O (3×) and brine (1×). Purification by silica gel chromatography (Isco) gave the desired product, (39 mg, 37%). Calcd for C32H34F5NO2 (M+H) 559.60, Found 560.4.

The synthetic route of 64248-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HO, Chih Yung; US2009/105275; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 69113-59-3, 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. 69113-59-3, name is 3-Iodobenzonitrile belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

N-(3-Cyanophenyl)benzylamine (, entry 14) The general procedure under argon was followed using copper(I) iodide (10 mg, 0.05 mmol), K3PO4 (425 mg, 2.00 mmol), benzylamine (131 muL, 1.20 mmol), 3-iodobenzonitrile (229 mg, 1.00 mmol), ethylene glycol (111 muL, 2.00 mmol) and 2-propanol (1.0 mL). Column chromatography using a solvent mixture (hexane/ethyl acetate=5/1, Rf=0.5) afforded N-(3-cyanophenyl)benzylamine (165 mg, 80% isolated yield) as light yellow solid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity.

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, 3-Iodobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Buchwald, Stephen L.; Klapars, Artis; Antilla, Jon C.; Job, Gabriel E.; Wolter, Martina; Kwong, Fuk Y.; Nordmann, Gero; Hennessy, Edward J.; US2003/65187; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 64248-58-4,Some common heterocyclic compound, 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, molecular formula is C6H3F2I, 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.

A mixture of zinc dust (980 mg, 15 mmol, Aldrich, -325 mesh) and dry tetrahydrofuran (3 mL) under argon was treated with 1,2-dibromoethane (0.37 g, 2 mmol). The zinc suspension was then heated with a heat gun to ebullition, allowed to cool, and heated again. This process was repeated three times to make sure the zinc dust was activated. The activated zinc dust suspension was then treated with trimethylsilyl chloride (82 mg, 0.75 mmol), and the suspension was stirred for 15 min at 25 C. The reaction mixture was then treated dropwise with a solution of (E)-3-cyclohexyl-2-iodo-acrylic acid methyl ester (prepared in Example 4, 1.47 g, 5 mmol) in dry tetrahydrofuran (1.5 mL) over 3 min. During the addition, the temperature rose to 45 C. The reaction mixture was then stirred at 40-45 C. for 1 h and then stirred overnight at 25 C. The reaction mixture was then diluted with dry tetrahydrofuran (5 mL), and the stirring was stopped to allow the excess zinc dust to settle down (2 h). In a separate reaction flask, bis(dibenzylideneacetone)palladium(0) (54 mg, 0.1 mmol) and triphenylphosphine (104 mg, 0.4 mmol) in dry tetrahydrofuran (10 mL) was stirred at 25 C. under argon for 10 min and then treated with 3,4-difluoro-iodobenzene (960 mg, 4 mmol) and the freshly prepared zinc compound in tetrahydrofuran. The resulting brick red solution was heated at 25 C. for 15 h, at which time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution (50 mL), and the organic compound was extracted into diethyl ether (250 mL), The combined organic extracts were washed with a saturated aqueous sodium chloride solution (150 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 5/1 hexanes/diethyl ether) afforded (E)-3-cyclohexyl 2-(3,4-difluoro-phenyl)-acrylic acid methyl ester (1.06 g, 95%) as an oil: EI-HRMS m/e calcd for C16H18F2O2 (M+) 280.1275, found 280.1275.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Difluoro-4-iodobenzene, its application will become more common.

Reference:
Patent; Hoffmann-La Roche Inc.; US6353111; (2002); B1;,
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 71838-16-9 as follows. Application In Synthesis of 2-Bromo-1-iodo-4-methylbenzene

Step 1: Preparation of 2-(2-bromo-4-methylphenyl)-1,3-difluoropropan-2-ol To a solution of 2-bromo-1-iodo-4-methylbenzene (18.5 g, 62.3 mmol) in THF (25 mL) at 0 C. was slowly added i-PrMgCl (24 mL, 24 mmol). After being stirred for 1 h at 0 C., the reaction mixture was cooled to -78 C. Then a solution of 1,3-difluoropropan-2-one (0.85 g, 9.04 mmol) in dry THF (25 mL) was added. The mixture was stirred at -70 C. for 1 h, and then dry ice bath was removed. The solution was acidified with HCl (2 N) and extracted with EA (60 mL*2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel, eluting with PE:EA (5:1) to give 2-(2-bromo-4-methylphenyl)-1,3-difluoropropan-2-ol (1.3 g, yield 55%) as colorless oil. 1H NMR (400 MHz, DMSO-d6): delta 7.60 (d, 1H), 7.46 (s, 1H), 7.21 (d, 1H), 6.21 (s, 1H), 4.97-4.94 (m, 1H), 4.85-4.82 (m, 2H), 4.74-4.71 (m, 1H), 2.26 (s, 3H) ppm.

According to the analysis of related databases, 71838-16-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anacor Pharmaceuticals, Inc.; Eli Lilly and Company; AKAMA, Tsutomu; Balko, Terry William; Defauw, Jean Marie; Plattner, Jacob J.; White, William Hunter; Winkle, Joseph Raymond; Zhang, Yong-Kang; Zhou, Yasheen; US2013/131017; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

19230-28-5, name is 1,3-Dichloro-2-iodobenzene, 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. Quality Control of 1,3-Dichloro-2-iodobenzene

[0064] To a vigorously stirred solution of magnesium turnings (1.250 g, 50.50 mmol) in 180 mL of dry THF1 bromoanisole (9.430 g, 50.50 mmol) was added slowly and the mixture was then refluxed for 2.5 hours. A cold solution of the 2,6- dichloroiodobenzene (6.818 g; 25.00 mmol) with vinylmagnesium bromide (1 equivalent; 32.5 mL of 0.7 M solution in cyclohexane) at -18 C was transfeired to the refluxing Grignard solution and stirred for 2.5 hours. The reaction mixture was brought to room temperature and CO2 was bubbled in overnight. It was then quenched with 150 niL of 6N HCl, extracted with Et2O (3×150 mL) and then washed with water and saturated NaHCO3. The crude mixture was purified by flash chromatography (silica gel; hexane:CH2Cl2 1 :4) and resulted in 14 as a white powder 42.6% (3.56 g).[0065] A mixture of 14 (3 g, 9 mmol), 14 mL of aqueous hydrobromic acid (d. 1.48), and 14 mL of 33% hydrogen bromide in glacial acetic acid was warmed with vigorous stirring for six hours under a dry carbon dioxide atmosphere. The mixture was then suspended in water. The resulting fine gray precipitate was dissolved in a small volume of 15% sodium hydroxide, filtered, and then precipitated with added concentrated hydrochloric acid. The resulting solid was added to a mixture of potassium carbonate (3.7 g, 27mmol) in DMF (100 mL). Methyl iodide (1.27 g, 9mmol) was added slowly to the mixture at 0C and stirred at room temperature for 4 hours. The reaction was quenched with 50 mL of 3N HCl and extracted with Et2theta (3×100 mL). The solvent was evaporated leaving the crude product 15, which was further purified by flash chromatography (silica gel; CH2Cl2: Methanol 1 :0.05).[0066] Tris(hydroxym ethyl )nitromethane 16 (10.0 g, 66.17 mmol) was dissolved in dry pyridine 60 mL and cooled to 0C. Tosylchloride (39.2 g, 211.00 mmol) in 80 mL pyridine was slowly added to this solution over 3.5 hours. The reaction mixture was stirred at room temperature overnight and quenched by adding ice. The product was extracted into CH2Cl2 and was successively washed with IM HCl, brine and water. The solvent was evaporated and the resulting white powder was dried over Na2SO4. Yield: 22.57 g; 55.6%.[0067] Tris(para-tolylsulfonylmethyl)nitromethane 17 (3.070 g, 5.0 mmol), and 15 (6.407g, 20 mmol) and NaOH (0.800 g, 20.0 mmol) were dissolved/suspended in 20 mL DMF and the reaction mixture was heated to reflux at 160C for 17 hours. After cooling to room temperature 100 mL water was added and the precipitate was isolated by filtration. The final product 18 was washed with water and MeOH. [0068] The final product 18 (5.3 g, 5.0 mmol) and tin(II) chloride (2.84 g, 15 mmol) were combined in ethanol (180 mL) and 37% HCl (50 mL). After being heated at 65C overnight, the reaction was cooled, and most of the ethanol was removed using a rotary evaporator. Water (50 mL) was added, and the resulting precipitate was filtered, washed with water, and dried under high vacuum to give the product as the hydrochloride salt of Compound III.

The synthetic route of 19230-28-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; REBEK, Julius, Jr.; BERRYMAN, Orion B.; SATHER, Aaron C.; WO2010/138720; (2010); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 4387-36-4, name is 2-Iodobenzonitrile, molecular formula is C7H4IN, 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. Product Details of 4387-36-4

The specific reaction operation is:100 mmol of the compound of the above formula (II), 150 mmol of the compound of the above formula (III), and 0.8 mmol of palladium acetate are added to an appropriate amount of the organic solvent N,N-dimethylacetamide (DMA) at room temperature.100 mmol of tetra-n-butylammonium bromide and 225 mmol of sodium carbonate,Then stir to warm to 95 ° C,And stirring the reaction at this temperature for 25 hours;After the reaction was completed, the reaction mixture was poured into a sufficient amount of ethyl acetate.After washing with saturated brine, the organic layer and the aqueous layer were separated.After the aqueous layer is sufficiently extracted with ethyl acetate,The combined organic layers (i.e., the organic layer washed with saturated brine and organic layer extracted from ethyl acetate) were dried over anhydrous Na2SO?The residue was eluted by flash column chromatography (a mixture of petroleum ether and ethyl acetate in a ratio of 8:1 as eluent).The eluent was collected and evaporated to remove the eluent.Thereby obtaining a compound of the above formula (I) as a white solid,The yield was 87.6percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4387-36-4, its application will become more common.

Reference:
Patent; Wenzhou Medical University Affiliated The Second Hospital ? Wenzhou Medical University Affiliated Yuying Child Hospital; Wenzhou Medical University; Wang Zhiyi; Pan Chenwei; Chen Chan; Weng Jie; Wang Xianqin; Xu Tong; Wu He; (10 pag.)CN108250103; (2018); A;,
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. 450412-28-9, name is 1-Bromo-3-chloro-2-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H3BrClI

A sdution of 5-(44,5,5-tetramethy-1 32-doxabordan-2-yndohn-2-one (250 mg, 0.96 mmd), 1-bromo-3-choro-2-odobenzene (373mg, 1.2 mmd), and potassum phosphate (410 mg, 1.9 mmd) n 4:1 doxane: water (3.0 rnL) was degassed with n[trogen for 10 minutes. PdC2(dppf)-CH2C2 (35 mg, 0.05 mmd) was added at once and the resuWng mixture was degassed w[th n[trogen for an add Wona 10 minutes. The reacUon rnxturewas heated at 100 C for 16 h. After coohng to rt, water was added and the aqueous ayer was extracted w[th DCM (x3). The combined orgadc extracts were dried over Na2SO4 and concentrated n vacuo. Purflcafion (FCC, SO2; 0 50% EtOAc/hexanes) provided the tWe compound as a white sohd (189 mg, 61% yed). MS (ES): mass cacd. for C14H9BrCNO, 321.0; rn/z found. 321.9 [M+Hj. 1H NMR (500 MHz, DMSO-d6) oe 10.50 (5,IH), 772(dd, J=8.1, 1.1 Hz, IH), 760 (dd, J=8.1, 1.1 Hz, IH), 7.32(t, J=8.1 Hz, IH),7.11 -6.97 (m, 2H), 6.91 (dd, J=8.0, 0.6 Hz, IH), 353 (5, 2H).

According to the analysis of related databases, 450412-28-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; AMERIKS, Michael K.; RAVULA, Suchitra; SAVALL, Bradley M.; SWANSON, Devin M.; ZIFF, Jeannie M.; SHIREMAN, Brock T.; (167 pag.)WO2016/176463; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 7425-53-8, A common heterocyclic compound, 7425-53-8, name is Ethyl 4-iodobutanoate, molecular formula is C6H11IO2, 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: In a 5 mL round-bottom flask under argon containing zinc powder (197 mg, 3 mmol) and PdCl2(Amphos)2 (7 mg, 0.01 mmol) was added 2% PTS solution in water (1.5 mL). N,N,N’,N’-Tetramethylethylenediamine (TMEDA, 232 mg, 2 mmol) was added at rt followed by the addition of the alkyl halide (2 mmol) and the heteroaromatic halide (0.5 mmol). The flask was stirred vigorously at rt for the indicated time. The product was extracted with EtOAc.11 Silica gel (1 g) was added to the combined organic phase and solvents were removed under vacuum. The resulting dry, crude silica was introduced on top of a silica gel chromatography column to purify the product.

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; Krasovskiy, Arkady; Thome, Isabelle; Graff, Julien; Krasovskaya, Valeria; Konopelski, Paul; Duplais, Christophe; Lipshutz, Bruce H.; Tetrahedron Letters; vol. 52; 17; (2011); p. 2203 – 2205;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 88-82-4, 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. 88-82-4 name is 2,3,5-Triiodobenzoic 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.

Amide derivatives (Compounds 8 and 9) that correspond to the ester, Compound 5, are generated. Compounds 6 and 7 are synthesized and their coupling to 2,3,5-triiodobenzoic acid is carried out

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,3,5-Triiodobenzoic acid, and friends who are interested can also refer to it.

Reference:
Patent; Vanderbilt University; US2005/2859; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com