Month: December 2020

Adding some certain compound to certain chemical reactions, such as: 3032-81-3, name is 1,3-Dichloro-5-iodobenzene, 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 3032-81-3. 3032-81-3

a (3,5-Dichloro-phenylethynyl)-trimethyl-silane The title compound was synthesised from 1,3-dichloro-5-iodo-benzene using the procedure described in Example 18, step (a), in 98percent yield. 1H NMR (CDCl3) delta7.34-7.33 (m, 2H), 7.31-7.29 (m, 1H), 0.24 (s, 9 H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1,3-Dichloro-5-iodobenzene.

Reference:
Patent; 3-Dimensional Pharmaceuticals, Inc.; US2002/169200; (2002); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding some certain compound to certain chemical reactions, such as: 35944-64-0, name is 3-Iodo-4-methylaniline, 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 35944-64-0. 35944-64-0

2/6-Difluoro-N-(2′-methyl-5I-(pyridin-2-ylmethoxy)biphenyl-4-yl)benza?iotaide[00150] To a solution of 3-iodo-4-methylaniline (1 g, 4.29 mmol) in H2O (25 mL) was added H2SO4 (0.5 M, 25 mL). The solution was heated to 8O0C until all solid dissolved. Then the reaction was cooled to 00C, and NaNCh (0.44 g, 6.39 mmol) was added in small portions. After 2 hr at this temperature, urea (0.13 g, 2.1 mmol) was added at 00C. The solution was allowed to warm up to room temperature, and H2SO4 (0.5 M, 25 mL) was added. The reaction was refluxed for 30 min and cooled down to room temperature. The solution was extracted with EtOAc and EbO, and the combined organic phases were dried over Na2SO4, concentrated, and chromatographied to give the pure product 1 (0.8 g, 80%). Following the general Suzuki coupling procedure, 2 was prepared.[00151] The solution of 2 (0.4 g, 1.18 mmol), 2-picolyl chloride hydrochloride (0.215 g, 1.31 mmol), and K2CO3 (0.325 g, 2.35 mmol) in DMF (5 mL) was heated at 500C for 48 hr. The reaction solution was diluted with H2O (15 mL) and extracted with EtOAc (25 mL). Column chromatography (Hexanes/EtOAc=l/l) afforded Compound 4 in 56% yield.[00152] 1H NMR (400 MHz, CDCl3) delta 8.59 (d, / = 4.8 Hz, 1 H), 7.74-7.66 (m, 4 H), 7.55-7.52 (m, 1 H), 7.48-7.40 (m, 1 H), 7.34-7.32 (m, 2 H), 7.24-7.16 (m, 2 H), 7.02 (t, / = 8.0 Hz, 2 H), 6.90-6.87 (m, 2 H), 5.21 (s, 2 H), 2.21 (s, 3 H); ESMS cacld (C26H20F2N2O2): 430.1; found: 431.1 (M+H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3-Iodo-4-methylaniline.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; JIANG, Jun; ZHANG, Junyi; CHEN, Shoujun; SUN, Lijun; WO2010/39238; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 4102-53-8, name is 4-Iodo-2,6-dimethylaniline, A new synthetic method of this compound is introduced below., 4102-53-8

To a suspension of sodium bicarbonate (126 g, 1500 mmol) and 2,6-dimethylaniline (61.5 mL, 500 mmol) in methanol (700 mL) was added iodine monochloride (1.0 M in dichloromethane, 550 mL, 550 mmol) at room temperature over 1 h. After addition was complete, stirring was continued for 3 h. The reaction was filtered to remove excess sodium bicarbonate and the solvent removed in vacuo. The residue was redissolved in diethyl ether (1.5 L) and treated with hydrochloric acid (2M in ether, 375 mL, 750 mmol). The resulting suspension was stored in the freezer (-15 C.) overnight. The solid was filtered and washed with diethyl ether until it became colorless to give 126.5 g (89%) as a grey-green powder. 1H-NMR (DMSO-d6) delta 2.33 (s, 6H), 7.48 (s, 2H), 9.05 (bs, 3H); 13C-NMR (DMSO-d6) delta 17.4, 91.5, 133.1, 131.2, 136.9.

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; Chaturvedula, Prasad V.; Han, Xiaojan; Jiang, Xiang-Jun J.; US2006/122250; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

34683-73-3, name is 1-Chloro-6-iodohexane, 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. 34683-73-3

5-(7-Chloroheptyl)-3-methyl-isoxazole (VIII) 21.0 g (0.216 mol) of 3,5-dimethylisoxazole (VII) (prepared in accordance with the method of C. Kashima et al., Bull. Chem. Soc. Jap. 46, 310, 1973) are dissolved in 200 ml of absolute tetrahydrofuran, the solution is cooled to -80 C. and 160 ml of n-butyllithium (1.35M solution in n-hexane, 0.216 mol) are added dropwise at this temperature in the course of 40 minutes. The mixture is stirred at a temperature below -75 C. for a further 15 minutes. The reaction mixture is then added dropwise to a solution of 53.5 g (0.217 mol) of 1-iodo-6-chlorohexane (prepared in accordance with the method of W. F. Huber, J. Am. Chem. Soc. 73, 2730, 1951) in 150 ml of absolute tetrahydrofuran so that the temperature does not rise above -60 C. When the addition has ended, the mixture is stirred at -60 C. for a further 15 minutes and allowed to warm to room temperature. The reaction mixture is partitioned between methylene chloride and 0.2N HCl, the aqueous phase is extracted three more times with methylene chloride and the combined organic phases are dried over sodium sulfate and evaporated. The crude product (about 45 g) is distilled in portions in a bulb tube (air bath temperature 80 C./0.2 mbar). Yield: 26.9 g of a yellowish oil.

Statistics shows that 34683-73-3 is playing an increasingly important role. we look forward to future research findings about 1-Chloro-6-iodohexane.

Reference:
Patent; Chemie Linz Akteingesellschaft; US4812472; (1989); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

696-41-3, Adding some certain compound to certain chemical reactions, such as: 696-41-3, name is 3-Iodobenzaldehyde, 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 696-41-3.

General procedure: A mixture of an aldehyde (1) (1.0 equiv), 2-aminobenzophenone (2) (1.0equiv), NH4OAc (3) (2.0 equiv), and DMAP (0.2 equiv.) in absolute EtOH (5 ml)was stirred at 40 C for the stipulated period of time (see Tables 2 and 3). Aftercompletion of the reaction, as monitored by TLC, the mixture was poured intoice-cold H2O and the solid product was filtered, washed with H2O (3-5 mL) anddried. The crude product was recrystallized from EtOAc to give puredihydroquinazolines. For compounds 4c, 4g, 4m, and 4p, after cooling, H2Owas added and the product was extracted with EtOAc (3 15 mL). Thecombined organic extract was washed with H2O, dried (anhyd Na2SO4) and thesolvent removed followed by flash column chromatography over silica gel (60-120 mesh) to furnish the desired product.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 696-41-3.

Reference:
Article; Derabli, Chamseddine; Boulcina, Raouf; Kirsch, Gilbert; Carboni, Bertrand; Debache, Abdelmadjid; Tetrahedron Letters; vol. 55; 1; (2014); p. 200 – 204;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 31599-60-7, name is 1-Iodo-2,3-dimethylbenzene, 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. 31599-60-7

To a solution of 1-iodo-2,3- dimethylbenzene (8) [prepared according to Chen, Y et al. Org. Lett. 2007, 9, 1899] (1 .93 g, 8.32 mmol) in carbon tetrachloride (40 mL) was added NBS (3.67 g, 20.62 mmol), AIBN (0.070 g, 0.43 mmol) and the resulting mixture was gently refluxed by irradiation with a halogen lamp (500 W) for 4 h. The precipitate was filtered and washed with a small amount of carbon tetrachloride. The filtrate was concentrated under reduce pressure, the obtained residue was dissolved in EtOAc ( 1 00 ml), successively washed with 10% NaOH solution (20 mL), water (2 x 20 ml), 10% Na2S203 solution (20 mL), water (20 mL), brine (20 raL), and dried (Na2SC>4). The solvent was evaporated and the residue was purified by column chromatography on silica gel (eluent petroleum ether) to give 1 .89 g (58.3%) of compound 9. NMR (CDC13) delta: 7.84 (dd, J=8.1 , 1 .1 Hz, 1 H), 7.33 (dd, J=7.6, 1 .1 Hz, l H), 6.97 (t, J=7.8 Hz, 1 H), 4.85 (s, 2H), 4.66 (s, 2H). The product contained ca. 15-20% of an inseparable impurity (supposedly l -bromo-2,3-bis(bromomethyl)benzene).A mixture of 1,2-bis(bromomethyl)-3-iodobenzene (9) (2.50 g, 6.41 mmol), diethyl 2-acetamidomalonate (1 .39 g, 6.41 mmol), and K2C03 (2.22 g, 1 6.06 mmol) in acetonitrile (40 mL) was refluxed for 70 h. The mixture was allowed to cool to ambient temperature, the precipitate was filtered and washed with a small amount of acetonitrile. The filtrate was concentrated under reduce pressure, the obtained residue was dissolved in EtOAc (100 mL), washed successively with saturated NaHC03 solution (30 mL), water (2 x 30 mL), brine (30 mL), and dried (Na2S04). The solvent was evaporated and the residue was purified by column chromatography on silica gel (eluent petroleum ether-ethyl acetate, gradient from 20: 1 to 20:6) to give 2 g of oil. The oil was dissolved in diethyl ether and kept in a refrigerator overnight. The precipitate was filtered and dried to give 0.4 g (14%) of a regioisomer diethyl 2-acetyl-5-iodo-l ,4-dihydroisoquinoline-3,3(2H)-dicarboxylate. NMR (CDC13) delta: 7.76 (d, J=8.0 Hz, 1H), 7.13 (d, J=7.5 Hz, 1 H), 6.94 (t, J = 7.7 Hz, 1H), 4.65 (s, 2H), 4.19 (q, J=7.1 Hz, 2H), 4.16 (q, J=7.1 Hz, 2H), 3.56 (s, 2H), 2.28 (s, 3H), 1 .22 (t, J=7.1 Hz, 3H), 1.22 (t, J=7.1 Hz, 3H). LCMS (ESI) m/z: 446 [M+H]+. The filtrate was evaporated and the residue was purified by column chromatography on silicagel (eluent petroleum ether-ethyl acetate, gradient from 20: 1 to 20:6) to give 0.95 g (33.2%) of compound (10).A solution of diethyl 2-acetyl-8-iodo-l,4-dihydroisoquinoline-3,3(2H)-dicarboxylate (10) (0.585 mmol) in 6 N HQ (10 mL) was refluxed for 5 h. The mixture was cooled and cone. NH4OH water solution was added until pH of the medium was ~7. The precipitate was filtered, washed with a small amount of water, and dried to give 0.305 g (76.7%) of compound (11). Because of a low solubility of the product in common deuterated organic solvents and deuterium oxide, the NMR spectrum was not informative. LCMS (ESI) m/z: 304 [M+H]+. The product contained ca. 15-20% of an inseparable impurity (supposedly the corresponding bromo derivative 8-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid). LCMS (ESI) m/z: 256 [M+H]+.To a suspension of 8-iodo-l ,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (11) (0.645 g, 2.13 mmol) in methanol ( 1 8 mL) slowly SOCI2 ( 1.07 ml, 14.92 mmol) was added within 10 min. The reaction mixture was stirred at room temperature for 16 h, evaporated, and the residue was dissolved in a mixture of IN NaHC03 solution (30 mL) and EtOAc (50 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2 ^ 15 mL). The organic extracts were combined, washed successively with water (20 mL), brine (20 mL), and dried (Na2S04). The solvents were evaporated to give compound 12 (0.570 g, 84%) which was used in the next step without further purification. NMR (CDCI3) delta: 7.67 (d, J=7.8 Hz, IH), 7.10 (d, J=7.5 Hz, I H), 6.87 (t, J=7.7 Hz, IH), 4.07 (d, 16.6 Hz, IH), 3.87 (d, J=16.6 Hz, I H), 3.78 (s, 3H), 3.71 (dd, J=9.4, 5.0 Hz, I H), 3.04 (dd, J=16.5, 5.0 Hz, IH), 2.97 (dd, J=l 6.5, 9.4 Hz, IH). LCMS (ESI) m/z: 318 [M+H]+. The product contained ca. 15-20% of an inseparable impurity (supposedly the corresponding bromo derivative methyl 8-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate). LCMS (ESI) m/z: 270 [M+H]+.A mixture of methyl 8-iodo-1, 2,3,4- tetrahydroisoquinoline-3-carboxylate (12) (0.570 g, 1 .8 mmol) and 2,3-dichloro-5,6-dicyano- 1 ,4-benzoquinone (DDQ) (0.449 g, 2.0 mmol) in toluene (20 mL) was refluxed for 6 h. To the reaction mixture was added another portion of DDQ (0.100 g, 0.45 mmol) and the refluxing was continued for 16 h. The mixture was allowed to cool to room temperature; the precipitate was filtered and washed with a small amount of toluene. The filtrate was evaporated and the residue was purified by column chromatography on silicagel (eluent petroleum ether-ethyl acetate, gradient from 100:0 to 100: …

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 31599-60-7.

Reference:
Patent; LATVIAN INSTITUTE OF ORGANIC SYNTHESIS; JIRGENSONS, Aigars; LOZA, Einars; CHARLTON, Michael; FINN, Paul William; RIBAS DE POUPLANA, Lluis; SAINT-LEGER, Adelaide; (76 pag.)WO2016/129983; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

2401-21-0, These common heterocyclic compound, 2401-21-0, name is 1,2-Dichloro-3-iodobenzene, 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.

Method C 2,3-Dichloroiodobenzene (350 g, 1.282 mol) dissolved in dry ether (1250 ml) was added slowly, with stirring, to magnesium turnings (30.77 g, 1.282 mol) in dry diethyl ether (300 ml), in order to form 2,3-dichlorophenylmagnesium iodide under nitrogen.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2401-21-0.

Reference:
Patent; Glaxo Wellcome Inc.; US5912345; (1999); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

88-67-5, 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. 88-67-5, name is 2-Iodobenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Add compound 5 (8.44 g, 34.03 mmol) to a 250 ml round bottom flaskAnd 60ml concentrated sulfuric acid, stir to 60 C and add N-bromosuccinimide(4.82 g, 38.06 mmol), reacted for 2 h, and after cooling to room temperature, the solution was dropped into ice water.Extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure.Column chromatography gave 9.54 g of white solidCompound 6, yield 86%.

The synthetic route of 2-Iodobenzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dalian University of Technology; Wang Shisheng; Li Guangzhe; Liu Liqiang; Zhao Weijie; Guo Xiuhan; Li Yueqing; Wang Xu; Dong Huijuan; (21 pag.)CN110041200; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-75-9,Some common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, molecular formula is C2H2IN, 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.

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)

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

Reference:
Patent; Kalla, Rao; Perry, Thao; Elzein, Elfatih; Varkhedkar, Vaibhav; Li, Xiaofen; Ibrahim, Prabha; Palle, Venkata; Xiao, Dengming; Zablocki, Jeff; US2003/229106; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-75-9, Adding a certain compound to certain chemical reactions, such as: 624-75-9, name is 2-Iodoacetonitrile, 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 624-75-9.

The compound obtained in Example 64 (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. 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 the residue was treated in 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 regioisomers as yellow oil. These two regioisomers (4.16 g, 80%) were used in the next reaction step without separation.Example 65-2Preparation of 4-(2-chloropyridin-5-yl)-5-(3-methoxy-5-methylphenyl)-pyrazol-1-yl)acetonitrile1H NMR (CDCl3) delta 2.28 (s, 3H), 3.66 (s, 3H), 5.16 (s, 2H), 6.71 (s, 2H), 6.84 (s, 1H), 7.24 (d, J=8.3 Hz, 1H), 7.49 (dd, J=2.3, 5.9 Hz, 1H), 7.70 (s, 1H, 8.32 (s, 1H); 13C NMR (CDCl3) delta 21.57, 39.89, 55.23, 110.80, 113.76, 115.28, 117.76, 121.47, 124.02, 127.24, 129.92, 132.57, 138.58, 140.12, 148.71, 149.92, 151.17, 159.69, 162.33.To a solvent mixture of THF and water (4:1, 10 mL) were added the mixture prepared in Example 65 (400 mg, 1.18 mmol), 2-acetylphenyl boronic acid (023 g, 1.42 mmol), dichlorobis(triphenylphosphine)palladium (II) (41 mg, 0.06 mmol) and potassium carbonate (0.16 g, 1.18 mmol). The reaction system was purged with nitrogen gas for 10 min, 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): (155 mg); m.p. 176-177 C.; 1H NMR (CDCl3) delta 2.25 (s, 3H), 2.28 (s, 3H), 3.70 (s, 3H), 5.14 (s, 2H), 6.72 (s, 1H), 6.76 (s, 1H), 6.89 (s, 1H), 7.44-7.65 (m, 6H), 7.70 (s, 1H), 8.54 (s, 1H); 13C NMR (CDCl3) delta 21.51, 30.58, 39.79, 55.19, 110.80, 113.82, 115.30, 118.66, 121.54, 121.89, 127.06, 127.63, 128.80, 128.96, 130.02, 130.36, 132.92, 136.56, 138.15, 139.93, 141.68, 148.55, 151.23, 155.76, 159.71, 204.39.

According to the analysis of related databases, 624-75-9, the application of this compound in the production field has become more and more popular.

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