Tag: M.W=200-300

Related Products of 33348-34-4, A common heterocyclic compound, 33348-34-4, name is 4-Amino-3-iodobenzonitrile, molecular formula is C7H5IN2, 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: A 25 mL reaction tube was charged with 2-haloaniline 1 (0.6 mmol), potassium o-ethyldithiocarbonate 2 (1.8 mmol), FeF3 (0.06 mmol), 2,2?-bis(diphenylphosphino)-1,1?-binaphthyl (0.03 mmol) and DMF (4 mL). The reaction vessel was flushed with argon for three times and sealed. Then the mixture was stirred electromagnetically in an oil bath at 110 for 3 – 21 hours. The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, then 4 mL HCl (3mol/L) was added and stirred for 30 minutes. Then the reaction mixture solution was extracted by ethyl acetate (3*20 mL). Subsequently, the combined organic solution were dried by anhydrous sodium sulfate and the target product was purified by silica gel colum chromatography (eluent: petroleum ether / ethylacetate) to give the corresponding pure product 3.

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; Gao, Min; Lou, Chunqing; Zhu, Ning; Qin, Weijing; Suo, Quanling; Han, Limin; Hong, Hailong; Synthetic Communications; vol. 45; 20; (2015); p. 2378 – 2385;,
Iodide – Wikipedia,
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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. 204257-72-7, name is Methyl 2-fluoro-4-iodobenzoate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 2-fluoro-4-iodobenzoate

a. Methyl 2-fluoro-4-((3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2- yI)amino)benzoate (106). To a solution of 6 (1.7074 g, 7.86 mmol), 2 (2.2494 g, 8.03 mmol), CsCO3 (6.24 g, 19.2 mmol), rac-BJNAP (0.3 824 g, 0.6 14 mmol) in toluene (9.0 mL) in a 100 mL round-bottomed flask was added Pd2(dba)3 (0.3593 g, 0.39 mmol). The solution was sparged with nitrogen for 5 mm., then a reflux condenser was fitted to the flask, the atmosphere was evacuated and back-filled with nitrogen (three times), and the reaction was heated to reflux with stirring in an oil bath (125-120 C) for 22h. After cooling the reaction to room temperature, excess cesium carbonate and other solid particulates were filtered and washed with ethyl acetate, and the organic filtrate was concentrated in vacuo to give a crude product that was purified by column chromatography (150 mL Si02, 5% ethyl acetate:hexanes) to give 106 (1.9009 g, 65%) as a crystalline solid, m.p. 159.7-165.1C: ?H NMR (400 MHz, CDC13)oe 7.79 (t,J 8.8, 1H), 7.17 (d,J= 3.6, 1H), 6.51 (dd,J= 8.8, 2.0, 1H), 6.38 (dd, J= 13.6, 2.0 1H), 5.74 (br s, 1H), 3.87 (s, 3H), 2.17 (s, 3H), 1.68 (s, 4H), 1.29 (s, 6H),1.24 (s, 6H); ?3C NMR (100.6 MHz, CDC13) oe 165.3, 165.0, 164.9, 162.7, 151.9, 151.8, 143.9, 142.6,135.2, 133.6, 133.5, 129.9, 129.1, 122.5, 109.6, 109.5, 107.5, 107.4, 100.9, 100.6, 51.7, 35.0. 34.9,34.0, 33.9, 31.8; JR (neat) 3346, 2922, 1698, 1606, 1264 cm?; ES-MS (M+Na)+ calcd for C23H28FNO2Na 392.2002, found 392.2003.

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:
Patent; ARIZONA BOARD OF REGENTS ON BEHALF OF ARIZONA STATE UNIVERSITY; WAGNER, Carl; MARSHALL, Pamela; JURUTKA, Peter; WO2015/130973; (2015); A1;,
Iodide – Wikipedia,
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Related Products of 6293-83-0,Some common heterocyclic compound, 6293-83-0, name is 2-Iodo-4-nitroaniline, molecular formula is C6H5IN2O2, 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.

V-Benzyl-5-bromo-2-iodobenzamide (805 mg, 1.93 mmol), 2-iodo-4-nitroaniline (425 mg, 1.61 mmol), copper(I) iodide (123 mg, 0.65 mmol), and potassium carbonate (1.11 g, 8.0 mmol) were taken up in anhydrous DMSO (1 1 mL). The resulting reaction mixture was first stirred at 80C for 2 hr, followed by heating to 135 C for another 16 hr. After cooling to room temperature, the mixture was diluted with an excess of EtzO and washed with water. The organic layer was dried over NaiSO-s, filtered and concentrated. The residue was purified by flash column chromatography (EtOAc : Hex = 0 : 100 to 100 : 0) to give 10-benzyl -2-bromo-8- nitro-5,10-dihydro- 1 1/7-dibenzo[¡ê>,e][l ,4]diazepin-l l-one (179 mg, 26 %).

The synthetic route of 6293-83-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael S.; DE CLERCQ, Dries; JANG, Jaebong; JANNE, Pasi; TO, Ciric; ECK, Michael; PARK, Eunyoung; HEPPNER, David; (0 pag.)WO2019/164948; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 723294-75-5, 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. 723294-75-5 name is 3-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.

Procedure for preparation of compound 2:To a solution of 13 (1000mg, 0.46mmoi) and 14 (135.8mg, 0.SSmmoi) in DMSO (2OmL) was added CuT (95mg, 0.OSmmol) and C52C03 (399.7mg, 0.92mmoi) at rt, the mixture was stirred at 100C for lOh under N2 atmosphere. The solution was diluted with EtOAc (lOmL), washedwith water, biine (iOmnL), dried over anhydrous Na2SO4, filtered and concentrated to dryness. The residue was purified by prep-TLC to afford the target product Compound 2 (5.0mg, yield:3.2 % LCMS: m/z, 338.0 ?M+H)1INNIR (400 MHz, CDCI3): .59 (d, j:::: 4.4 Hz, 111), 7.88 (d, j:::: 6.8 Hz, 1H), 759-752(m, 3H), 750-745 (m, 3H), 7.32-7.28 (m, 3H), 7.19-7.17 (m, 1H).

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

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; LI, Yongguo; (44 pag.)WO2017/173604; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 191348-14-8, 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. 191348-14-8, name is 2-Iodo-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A 25 mL Wattecs reaction tube was charged with 2-haloaniline 1 (0.6 mmol), potassium O-ethyl dithiocarbonate 2 (1.8 mmol),CuCl (0.06 mmol), and DMF (2 mL). The reaction vessel was flushed with argon three times and sealed. Then the mixture was stirred electromagnetically in an oil bath at 110C for 6 h.The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, and then HCl (3 mL, 3 mol/L) was added and stirred for another 30 min. The reaction mixture solution was extracted by ethyl acetate (3 ¡Á 20 mL). Subsequently, the combined organic solutions were dried by anhydrous sodium sulfate and the target product was purified by chromatography on a silica gel column (eluent: petroleum ether/ethyl acetate) togive the corresponding pure product 3. Complete characterization characterizationof the products (all known) is found in the Supplemental Materials (Figures S1-S13).

The chemical industry reduces the impact on the environment during synthesis 2-Iodo-4-methoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Liu, Lei; Zhu, Ning; Gao, Min; Zhao, Xiaole; Han, Limin; Hong, Hailong; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; 5; (2016); p. 699 – 701;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

461-17-6, name is 1,1,1-Trifluoro-4-iodobutane, 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 1,1,1-Trifluoro-4-iodobutane

The alcohol of Example A12 (0.50 g, 1.23 mmol), tetrabutylammonium bromide (79 mg, 0.246 mmol), and KOH (207 mg, 3.69 mmol) were slurried in xylene (5 mL). Afterward, 4,4,4-trifluoromethyl-1-iodobutane (0.88 g, 3.69 mmol) was added, and the resulting mixture was stirred in a sealed vial at 80 C. over the weekend. Subsequently, the mixture was filtered through celite and concentrated under N2. Chromatography (on silica, ethyl acetate/hexanes) afforded the ether in the form of a colorless oil (296.4 mg, 46.7% yield). NMR(CDCl3) delta 1.25-1.42 (m, 7H), 1.52 (s, 9H), 1.55 (d, 2H), 1.67 (d, 2H), 1.75-1.84 (m, 2H), 2.06-2.24 (m, 4H), 2.32 (d, 2H), 2.92 (t, 2H), 3.40 (t, 2H), 3.38 (t, 2H), 3.43 (t, 2H), 3.72-3.82 (m, 2H), 3.95 (dd, 2H). ESMS m/z=516.44 (M+H)+.

The synthetic route of 461-17-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Brown, David L.; Carroll, Jeffery N.; Chen, Yiyuan; Fobian, Yvette M.; Freskos, John N.; Gasiecki, Alan F.; Grapperhaus, Margaret L.; Heintz, Robert M.; Hockerman, Susan L.; Kassab, Darren J.; Khanna, Ish K.; Kolodziej, Stephen A.; Massa, Mark A.; McDonald, Joseph J.; Mischke, Brent V.; Mischke, Deborah A.; Mullins, Patrick B.; Nagy, Mark A.; Norton, Monica B.; Rico, Joseph G.; Schmidt, Michelle A.; Stehle, Nathan W.; Talley, John J.; Vernier, William F.; Villamil, Clara I.; Wang, Lijuan J.; Wynn, Thomas A.; US2005/9838; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 455-13-0, name is 4-Iodobenzotrifluoride, 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 455-13-0, Quality Control of 4-Iodobenzotrifluoride

Add in a 50 mL autoclave, add 5 mL of toluene, 1 mmol of 4-trifluoromethyliodobenzene, 1.2 mmol of phenylacetylene, 2.0 mmol of triethylamine, 0.5 mol% of benzimidazole, azacyclocarbene palladium Metal complex (relative to iodobenzene).The reactor was sealed, and the reactor was replaced three times with carbon monoxide to seal the reactor. The pressure of the CO gas was 2.0 MPa, and the temperature was slowly raised to 100 C by the temperature controller. The reaction was carried out for 18 hours, cooled to room temperature, and the kettle was discharged. The liquid obtained by the reaction was qualitatively analyzed by an Agilent 6890/5973 GC/MS.Target product1-(4-trifluoromethylphenyl)-3-phenyl-2-propyn-1-oneThe selectivity is greater than 99% and the isolated yield is 95%.

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; Chinese Academy Of Sciences Lanzhou Chemical Physics Institute; Liu Jianhua; Wang Bingyang; Yang Lei; Xia Chungu; Xu Chuanzhi; Zhao Kang; (22 pag.)CN109810147; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 13194-68-8, 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 13194-68-8 as follows.

EXAMPLE 1 4-Fluoro-2-(4-iodo-2-methylphenylamino)benzoic acid To a stirring solution comprised of 3.16 g (0.0133 mol) of 2-amino-5-iodotoluene in 5 mL of tetrahydrofuran at -78 C. was added 10 mL (0.020 mol) of a 2.0 M lithium diisopropylamide in tetrahydrofuran/heptane/ethenylbenzene (Aldrich) solution. The resulting green suspension was stirred vigorously for 15 minutes, after which time a solution of 1.00 g (0.00632 mol) of 2,4-difluorobenzoic acid in 10 mL of tetrahydrofuran was added. The reaction temperature was allowed to increase slowly to room temperature, at which temperature it was stirred for 2 days. The reaction mixture was concentrated. Aqueous HCl (10%) was added to the concentrate, and the solution was extracted with dichloromethane. The organic phase was dried (MgSO4) and then boiled over a steambath to low volume and cooled to room temperature. The off-white fibers were collected by vacuum filtration, rinsed with hexanes, and vacuum-oven dried. (76 C.; ca. 10 mm of Hg) to afford 1.10 g (47%) of the desired material; mp 224-229.5 C.; 1H NMR (400 MHz; DMSO): Lambda 9.72 (s, 1H), 7.97 (dd, 1H, J=7.0, 8.7 Hz), 7.70 (d, 1H, J=1.5 Hz), 7.57 (dd, 1H, J=8.4, 1.9 Hz), 7.17 (d, 1H, J=8.2 Hz), 6.61-6.53 (m, 2H), 2.18 (s, 3H); 13C NMR (100 MHz; DMSO): Lambda 169.87, 167.60, 165.12, 150.17, 150.05, 139.83, 138.49, 136.07, 135.31, 135.20, 135.07, 125.60, 109.32, 105.09, 104.87, 99.72, 99.46, 89.43, 17.52; 19F NMR (376 MHz; DMSO): delta-104.00 to -104.07 (m); IR (KBr) 1670 (C=O stretch) cm-1; MS (CI) M+1=372. Analysis calculated for C14H11FINO2: C, 45.31; H, 2.99; N, 3.77. Found: C, 45.21; H, 2.77; N, 3.64.

According to the analysis of related databases, 13194-68-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Warner-Lambert Company; US6310060; (2001); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 10297-05-9, These common heterocyclic compound, 10297-05-9, name is 1-Chloro-4-iodobutane, 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.

First, 1-chloro-4-iodobutane (1.00 g, 4.57 mmol) was dissolved into a mixture solvent of diethyl ether/pentane (2:3) to obtain a concentration of 0.10 M, the resultant mixture was cooled to -78¡ã C. t-butyl lithium (3.690 g, 9.610 mmol, 1.7M solution in pentane) was added gradually to the cooled solution of 1-chloro-4-iodobutane and stirred for 2 hours. 1,5-dichloropentane-3-one (838 mg, 4.580 mmol) dissolved in diethyl ether (8 mL) was added gradually to the reaction mixture. The reaction mixture was stirred for additional 4 hours at -78¡ã C., and then ice water (50 mL) was added to quench the reaction path, followed by extraction with diethyl ether. The organic layer was collected and dried over anhydrous magnesium sulfate and filtered, the solvents were removed under reduced pressure. The obtained crude product was purified by column chromatography using silica gel (hexane:ethyl acetate=5:1) to obtain 820 mg of compound 17 (yield 65percent).1H NMR (CDCl3): delta 3.52 (t, J=6.4 Hz, 6H, CH2Cl), 1.80-1.73 (m, 6H, CH2), 1.56-1.52 (m, 4H, CH2), 1.42 (s, 4H, CH2) ppm. 13C{1H} NMR (CDCl3): delta 73.58, 45.69, 44.95, 38.29, 36.48, 32.94, 26.96, 20.88 ppm.

The synthetic route of 10297-05-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SK ENERGY CO., LTD.; US2012/165549; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 19094-56-5, The chemical industry reduces the impact on the environment during synthesis 19094-56-5, name is 2-Chloro-5-iodobenzoic acid, I believe this compound will play a more active role in future production and life.

Oxalylchloride (176 kg; 1386 mol; 1.14 eq) is added to a mixture of 2-chloro-5-iodo benzoic acid (343 kg; 1214 mol) (compound IX.1), fluorobenzene (858 kg) and N,N-dimethylformamide (2 kg) within 3 hours at a temperature in the range from about 25 to 30¡ã C. (gas formation). After completion of the addition, the reaction mixture is stirred for additional 2 hours at a temperature of about 25 to 30¡ã C. The solvent (291 kg) is distilled off at a temperature between 40 and 45¡ã C. (p=200 mbar). Then the reaction solution (911 kg) is added to aluminiumchloride AlCl3 (181 kg) and fluorobenzene (192 kg) at a temperature between about 25 and 30¡ã C. 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 30¡ã C. and stirred for an additional hour. After phase separation the organic phase (1200 kg) is separated into two halves (600 kg each). From the first half of the organic phase solvent (172 kg) is distilled off at a temperature of about 40 to 50¡ã C. (p=200 mbar). Then 2-propanole (640 kg) is added. The solution is heated to about 50¡ã C. 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; 40 kg) after filtration. Solvent (721 kg) is distilled off at a temperature of about 40 to 50¡ã C. and p=200 mbar. Then 2-propanole (240 kg) is added at a temperature in the range between about 40 to 50¡ã C. If the content of fluorobenzene is greater than 1percent as determined via GC, another 140 kg of solvent are distilled off and 2-propanole (140 kg) is added. Then the solution is cooled from about 50¡ã C. to 40¡ã C. within one hour and seeding crystals (50 g) are added. The solution is further cooled from about 40¡ã C. to 20¡ã C. within 2 hours. Water (450 kg) is added at about 20¡ã C. within 1 hour and the suspension is stirred at about 20¡ã C. for an additional hour before the suspension is filtered. The filter cake is washed with 2-propanole/water (1:1; 800 kg). The product is dried until a water level of <0.06percent w/w is obtained. The second half of the organic phase is processed identically. A total of 410 kg (94percent yield) of product which has a white to off-white crystalline appearance, is obtained. The identity of the product is determined via infrared spectrometry. 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-Chloro-5-iodobenzoic acid, other downstream synthetic routes, hurry up and to see. Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/237526; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com