Tag: M.W=200-300

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. 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

General procedure: To a screw-capped vial (50 ml) were added aryl iodides 1(1.0 mmol), benzonitrile 2a (155 mg, 1.5 mmol), K2CO3 (276 mg,2.0 mmol), NaOH (40 mg,1.0 mmol), CuI (19 mg, 0.1 mmol), DMEDA(9 mg, 0.1 mmol), and [bmim]PF6 (14 mg, 0.05 mmol) in water(2 ml). The vial was flushed with nitrogen then sealed with the cap,and allowed to stir at 100 C for the specific reaction time. Thereaction mixture was extracted with EtOAc (315 ml). The combined organic extracts were dried over Na2SO4 for 12 h andevaporated under vacuum. The crude products were purified ina silica gel column for further purification, using PE/EtOAc (5:1) asthe eluent.

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; Wang, Jichao; Yin, Xinchi; Wu, Jun; Wu, Datong; Pan, Yuanjiang; Tetrahedron; vol. 69; 48; (2013); p. 10463 – 10469;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 21304-38-1, 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. 21304-38-1 name is 4-Iodobenzene-1,2-diamine, 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.

To a solution of 4-iodo-l,2-phenylenediamine (0.47 g) in dichloromethane (3 ml) 3-(2- bromophenyl)glutaric anhydride (0.54 g) was added with stirring at rt. Almost instantaniously an resinous precipitate is formed. After 1 h at rt the solvent was removed by decantation and the residue dried in vacuo to give an amorphous solid (0.52 g). The solid is dissolved in 1,4-dioxane (1 ml) and 4M HCI in 1,4-dioxane (3 ml) is added. The resulting dark solution is heated to reflux for 1 h whereupon a precipitate is formed. After cooling to rt the precipitate is collected by suction filtration, washed with 1,4-dioxane and diethyl ether, and dried in vacuo to give 3- (2-bromophenyl)-4-(5-iodo-2-benzimidazolyl)butanoic acid HCI (0.27g) as light grey solid.1H-NMR (500 MHz, DMSOd6)): delta (ppm) = 2.81 (dd, J = 16.4, 7.4 Hz, IH), 2.88 (dd, J = 16.6, 7.0 Hz, IH), 3.44 (dd, J = 14.5, 8.4 Hz, IH), 3.54 (dd, J = 14.6, 7.0 Hz, IH), 4.16 (m, IH), 7.14 (dt, J = 7.8, 1.6 Hz, IH), 7.37 (dt, J = 7.7, 1.1 Hz, IH), 7.51 (dd, J = 8.0, 1.2 Hz, IH), 7.54 (m, 2H), 7.75 (dd, J = 8.6, 1.5 Hz, IH), 8.08 (d, J = 1.3 Hz, IH).13C-NMR and DEPT (125 MHz, DMSOd6) : delta (ppm) = 31.60 (CH2), 38.67 (CH2), 39.01 (CH), 89.46 (C), 115.75 (CH), 122.07 (CH), 123.60 (C), 128.20 (CH), 128.34 (br, CH), 128.89 (CH), 130.78 (C), 132.71 (CH), 132.86 (br, C), 133.67 (CH), 140.36 (C), 152.04 (C), 171.97 (CO).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Iodobenzene-1,2-diamine, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITAET DES SAARLANDES; ENGEL, Matthias; FROeHNER, Wolfgang; STROBA, Adriane; BIONDI, Ricardo M.; WO2010/43711; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, 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 460-37-7, category: iodides-buliding-blocks

Example 40/V-{[(2S)-5-FLUORO-7-(METHYLSULFONYL)-2,3-DIHYDRO-1 ,4-BENZODIOXIN-2- YL]METHYLJ-N-(S1S1S-TRIFLUOROPROPYL)AMINEA mixture of 1 -[(2S)-5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1 ,4-benzodioxin-2- 5 yl]methaneamine (0.3 g, 1.1 mmol), 1 ,1 ,1 -trifluoro-3-iodopropane (0.16 ml, 1.4 mmol) K2CO3 (0.32 g, 2.3 mmol) and ACN (4 ml) was heated under microwave radiation at 1200C for 30 min. The mixture was filtrated and evaporated to dryness and the product was purified by flash column chromatography (EtOAc).Yield: 0.12 g, 31 %. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M. p. 10 233C. MS m/z (rel. intensity, 70 eV) 357 (M+, 1 ), 274 (3), 127 (5), 126 (bp), 69 (3). [alpha]= -53 (MeOH).

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; NSAB, FILIAL AF NEUROSEARCH SWEDEN AB, SVERIGE; WO2009/133107; (2009); A1;,
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 5458-84-4 as follows. HPLC of Formula: C7H6INO3

Step 1 2-Methoxy-4-nitro-1-trifluoromethyl-benzene Following the procedure reported in JACS 2003, 125, 12502, 2-iodo-5-nitroanisole (2.79 g, 10.0 mmol), copper(I) iodide (2.2 eq, 4.19 g), and potassium fluoride (2.2 eq, 1.28 g) were dissolved in DMF. ClF2CCO2CH3 (4.4 eq, 4.7 ml) was added and the mixture was heated to 120 C. overnight. Upon cooling, the mixture was diluted with water and diethyl ether and filtered through celite. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (gradient 9:1 to 1:1 Hexanes/Ethyl Acetate) to give 2-methoxy-4-nitro-1-trifluoromethyl-benzene (1.13 g, 51.1%) as a yellow oil.

According to the analysis of related databases, 5458-84-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Brotherton-Pleiss, Christine E.; Caroon, Joan Marie; Lopez-Tapia, Francisco Javier; US2010/160388; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 618-91-7, name is Methyl 3-iodobenzoate, 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 618-91-7, Safety of Methyl 3-iodobenzoate

Dissolve methyl 3-iodobenzoate (2.0g, 7.63mmol) in THF (50mL), then add cuprous iodide (85mg, 0.44mmol) and bistriphenylphosphine palladium dichloride (150mg, 0.22mmol) ).Nitrogen was replaced three times. Under the protection of nitrogen, diethylamine (8.3 mL, 80 mmol) and trimethylsilylacetylene (1.7 mL, 12 mmol) were slowly added.Protected by nitrogen and reacted at room temperature for 24 hours.After the reaction was completed, it was filtered, and the filtrate was concentrated. Saturated brine (60 mL) was added and extracted with ethyl acetate (60 mL × 3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated.Separation and purification by silica gel column chromatography (PE / EtOAc (v / v) = 60/1) to obtain 1 g of oily yellow liquid, yield: 78%.

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Bing; Bai Shun; Yang Tiping; Zhou Youbo; Zhang Yingjun; Zheng Changchun; Luo Ming; Li Shixi; Peng Dahua; Wu Shuang; Xiong Jinfeng; (203 pag.)CN107344940; (2020); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 3930-83-4, These common heterocyclic compound, 3930-83-4, name is 2-Iodobenzamide, 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: To a solution of 2-iodobenzamide (3) or 2-bromonicotinamide (6) (2.0 mmol) in DMSO (3 mL), was added aldehyde (2.2 mmol), NaN3 (260 mg, 4.0 mmol), CuBr (29 mg, 0.2 mmol), and l-proline (46 mg, 0.4 mmol). The reaction mixture was stirred at 80 C under air. After disappearance of the reactant (monitored by TLC), water (30 mL) was added to the mixture, and then extracted with ethyl acetate (15 mL) for three times. The extraction was washed with saturated NaCl solution, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (10:1 to 3:1) as the eluent to give the desired products 5 or 7.

Statistics shows that 2-Iodobenzamide is playing an increasingly important role. we look forward to future research findings about 3930-83-4.

Reference:
Article; Li, Ting; Chen, Minglu; Yang, Lei; Xiong, Zhengxin; Wang, Yongwei; Li, Fei; Chen, Dongyin; Tetrahedron; vol. 72; 6; (2016); p. 868 – 874;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 4028-63-1, A common heterocyclic compound, 4028-63-1, name is 2,4,6-Trimethyliodobenzene, molecular formula is C9H11I, 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.

2,4,6-trimethyliodobenzene (12 mmol, 3 equiv), elemental selenium (12 mmol, 3 equiv), 5-methylbenzoxazole (4 mmol, 1 equiv), Cu(OAc) 2 (at room temperature) 0.4 mmol), ammonium hydrogencarbonate (12 mmol, 3 equiv) was added to the reaction tube, then filled with nitrogen, and replaced three times. Under a nitrogen reaction environment, 20 mL of DMF reaction solvent was then added, and the mixture was stirred at a reaction temperature of 140 ° C for 24 hours. After monitoring the reaction by thin layer chromatography, the reaction mixture was cooled, then diluted with ethyl acetate, and the diluted solution was transferred to a separating funnel, and extracted with saturated brine to separate the aqueous and organic phases, and then acetic acid. The aqueous phase was extracted three times with ethyl acetate. The organic phase was combined, 25 g of anhydrous sodium sulfate was added, and the mixture was allowed to stand for 30 min, and the filter cake was washed three times with 50 mL of ethyl acetate each time, then the solvent was spun off, and the product was separated by column chromatography. Deprotection: petroleum ether: diethyl ether = 98:2), yield 90percent, product weight 1.191 g.

The synthetic route of 4028-63-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wenzhou Medical University; Wu Ge; (9 pag.)CN108484518; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 33348-34-4, name is 4-Amino-3-iodobenzonitrile, 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 33348-34-4, Application In Synthesis of 4-Amino-3-iodobenzonitrile

2-(4,4-Dimethyl-[1,3,2]dioxaboronan-2-yl)-benzoic acid ethyl ester (19.84 g) , 2-iodo-4-cyanoaniline (18.47 g), tetrakis(triphenylphosphine) palladium (8.75 g) and potassium phosphate (35.36 g) were added to dioxane (360 ml), and the resulting mixture was heated under reflux overnight. The reaction solvent was cooled, and the produced solid was collected by filtration, washed with water and dried to thereby obtain 17.3 g (yield: quantitative) of the title compound as a yellow solid. 1H-NMR(DMSO-de) dppm: 7.47 (lH,d,J=8.5Hz), 7.6-8.0 (3H,m), 8.1-8.2 (IH,m), 8.3-8.4 (IH,m), 8.98 (IH,s), 12.05(lH,brs)

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; OTSUKA PHARMACEUTICAL CO., LTD.; WO2006/35954; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 340825-13-0, name is 6-Iodo-3,4-dihydronaphthalen-1(2H)-one, 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 340825-13-0, Application In Synthesis of 6-Iodo-3,4-dihydronaphthalen-1(2H)-one

A solution of 6-iodo-3,4-dihydronaphthalen-1(2B)-one (5.0 g, 18.38 minol), 4- fluorobenzenethiol (4.11 mL, 38.6 minol) and absolute ethanol (20 mL) was cooled with an ice-water bath and bubbled with HC1 gas until saturation was reached (observed by theformation of a white precipitate). The mixture was allowed to warm to rt and stirred overnight. The mixture was dissolved in ether (250 mL) and washed sequentially with water (2 x 125 mL), 0.5 M aqueous Na2CO3 (3 xlOO mL) and brine (100 mL). The organic layer was dried and concentrated to provide a solid (9.2 g) which was a mixture of thioketal and vinyl sulfide. The solid was dissolved in chloroform (150 mL) andcooled in an ice-water bath. A solution of mCPBA (35 g, 156 minol) in DCM (200 mL)was washed with brine (50 mL), dried, filtered, and the filter cake was washed with DCM(50 mL). The combined filtrates were added dropwise in portions to the chloroformsolution of the products from above until the reaction was completed as judged by LCMS(175 ml. of the mCPBA solution was needed). The mixture was cooled in an ice bath,filtered to remove the insoluble material, and the filtrate was stirred with 10% aqueousNa2S2O3 (120 mL) for 5 min. The organic phase was separated, washed sequentially with 10% aqueous Na2S2O3 (2 x 120 mL), 10% aqueous Na2CO3 (3 x 200 mL) and brine (150 mL), dried and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc-hexanes (gradient from 0-20%) to give 4-((4- fluorophenyl)sulfonyl)-7-iodo-1,2-dihydronaphthalene (5.3 g, 70% yield) as a white foamy solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Iodo-3,4-dihydronaphthalen-1(2H)-one, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BATT, Douglas G.; DHAR, T.G. Murali; (146 pag.)WO2018/71314; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 19094-56-5, name is 2-Chloro-5-iodobenzoic acid, molecular formula is C7H4ClIO2, 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. Recommanded Product: 19094-56-5

Example 1 : Synthesis of the fluoride VIII.1Oxalylchloride (176kg; 1386mol; 1 ,14eq) is added to a mixture of 2-chloro-5-iodo benzoic acid (343kg; 1214mol) (compound IX.1 ), fluorobenzene (858kg) and N,N- dimethylformamide (2kg) within 3 hours at a temperature in the range from about 25 to 30C (gas formation). After completion of the addition, the reaction mixture is stirred for additional 2 hours at a temperature of about 25 to 30C. The solvent (291 kg) is distilled off at a temperature between 40 and 45C (p=200mbar). Then the reaction solution (91 1 kg) is added to aluminiumchloride AICI3 (181 kg) andfluorobenzene (192kg) at a temperature between about 25 and 30C within 2 hours. The reaction solution is stirred at the same temperature for about an additional hour. Then the reaction mixture is added to an amount of 570 kg of water within about 2 hours at a temperature between about 20 and 30C and stirred for an additional hour. After phase separation the organic phase (1200kg) is separated into two halves (600kg each). From the first half of the organic phase solvent (172kg) is distilled off at a temperature of about 40 to 50C (p=200mbar). Then 2-propanole (640kg) is added. The solution is heated to about 50C and then filtered through a charcoal cartouche (clear filtration). The cartouche may be exchanged during filtration and washed with a fluorobenzene/2-propanole mixture (1 :4; 40kg) after filtration. Solvent (721 kg) is distilled off at a temperature of about 40 to 50C and p=200mbar. Then 2-propanole (240kg) is added at a temperature in the range between about 40 to 50C. If the content of fluorobenzene is greater than 1 % as determined via GC, another 140kg of solvent are distilled off and 2-propanole (140kg) is added. Then the solution is cooled from about 50C to 40C within one hour and seeding crystals (50g) are added. The solution is further cooled from about 40C to 20C within 2 hours. Water (450kg) is added at about 20C within 1 hour and the suspension is stirred at about 20C for an additional hour before the suspension is filtered. The filter cake is washed with 2-propanole/water (1 :1 ; 800kg). The product is dried until a water level of <0.06%w/w is obtained. The second half of the organic phase is processed identically. A total of 410kg (94%yield) of product which has a white to off-white crystalline appearance, is obtained. The identity of the product is determined via infrared spectrometry. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19094-56-5, its application will become more common. Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WEBER, Dirk; RENNER, Svenja; FIEDLER, Tobias; ORLICH, Simone; WO2011/39107; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com