Category: 624-75-9

Related Products of 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.

In a three-necked flask, add 40 g of raw material 2 and 12 g of catalyst 3 (R = 3,5-trifluoromethylbenzyl, R1 = vinyl, R2 = hydrogen) and 1.5 L of chlorobenzene, cool to 0 C with stirring, and add 300 ml 50% aqueous sodium hydroxide solution. Subsequently, 32 g of a solution of iodoacetonitrile (ICH2CN) in 500 ml of chlorobenzene was added. After the addition, the solution was stirred at 0 C until the TLC detection reaction was completed. 40 g of crude product, chiral purity (HPLC) = 72: 28, yield 80%. The crude product was recrystallized from 300 ml of ethyl acetate to obtain 25.0 g of white solid 4 with a yield of 52%, a specific rotation of + 102 (c = 1, chloroform), and a chiral HPLC ?99.92%.

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; Shanghai Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Li Ruipeng; Zhou Weicheng; Lin Kuaile; Chen Liang; Pan Jing; Zhou Ting; Liu Zhenren; Li Hongyan; (16 pag.)CN110563605; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 624-75-9, 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. 624-75-9, name is 2-Iodoacetonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 5-bromo-2-isopropyl-4-methoxy- phenol from step 4(0.831 g, 34 mmol) and K2C03 (0.562 g, 4.1 mmol) in 17 mE dimethyl formamide (DMF) was added iodoacetonitrile (0.594 g, 3.6 mmol). The mixture was warmed to 60 C. for 30 minutes and then allowed to cool to room temperature. After cooling to room temperature the mixture was taken up in SOmE of H20 and extracted with 1:1 toluene/ethyl acetate, washed with H20 and then with brine. The combined organic layers were dried over Na2504, filtered and concentrated in vacuo to give a crude solid. Purification via flash chromatography (1:1 hexane/CH2C12) afforded (5-bromo-2-isopropyl-4-methoxy-phenoxy)-aceto- nitrile (0.611 g, 63%) as a while solid.

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

Reference:
Patent; Ford, Anthony P.; McCarthy, Bruce G.; US2015/57299; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. Product Details of 624-75-9

A mixture of [4- (4-HYDROXYPHENYL) butyl] carbamic acid tert-butyl ester 31 (0.365 g, 1.37 mmol) and Cs2CO3 (0.672 g, 2.06 mmol) in anhydrous DMF (8 mL) was heated at 65 C for 30 min. IODOACETONITRILE (0.276 g, 1.651 mmol) was then added to the mixture in one portion. The mixture was stirred at 65 C overnight, and then cooled to room temperature. The precipitated solid was filtered, and the filtrate was partitioned between water and dichloromethane (each 50 mL). The organic layer was separated, washed with brine (3 x 50 mL), dried over anhydrous NA2S04 and concentrated under vacuum. The residue was chromatographed on silica gel, eluting with a mixture of diethyl ether/dichloromethane (6: 94, v/v), to afford the desired product 40 (0.109 g, 38% yield) as a colorless viscous OIL. 1H NMR (300 MHz, CDC13) : 8 1.43 (s, 9H), 1.57 (M, 4H), 2.60 (t, 2H), 3.15 (M, 2H), 4.49 (br, 1H), 4.75 (s, 2H), 6.91 (d, 2H), 7.13 (d, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 624-75-9, its application will become more common.

Reference:
Patent; PARION SCIENCES, INC.; WO2005/18644; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 624-75-9, A common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, molecular formula is C2H2IN, 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: Individual solutions of secondary N-alpha-trimethylsilylmethyl-N-benzylamines19 (5mmol) in acetonitrile (100mL) containing K2CO3 (10mmol) and 2-iodoacetonitrile (4.5mmol) were stirred for 12hat room temperature and concentrated in vacuo to give residues that were partitioned between water and CH2Cl2. The CH2Cl2 layers were dried and concentrated in vacuo to afford residues that were subjected to silica gel column chromatography (EtOAc/hexane=1: 15 – 1: 30) to yield corresponding alpha-aminonitiriles 11a18 (91%), 11b (74%), 11c (78%), 11d (85%), 11e (75%), 11f (75%), 11g (74%), 11h (75%), 11i (78%), 11j (78%) and 11k (66%). 11a (liq): 1H NMR 0.12 (s, 9H), 2.18 (s, 2H), 3.40 (s, 2H), 3.62 (s, 2H), 7.27-7.34 (m, 5H).

The synthetic route of 624-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lim, Suk Hyun; Cho, Dae Won; Choi, Jungkweon; An, Hyunjun; Shim, Jun Ho; Mariano, Patrick S.; Tetrahedron; vol. 73; 44; (2017); p. 6249 – 6261;,
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. 624-75-9, name is 2-Iodoacetonitrile, A new synthetic method of this compound is introduced below., Formula: C2H2IN

A 500-mL three-neck round-bottomed flask equipped with an addition funnel, thermometer and charged with 118a (6.70 g, 37.4 mmol), Iodoacetonitrile (12.5 g, 74.9 mmol), iron (II) sulfate heptahydrate (5.20 g, 18.7 mmol) and dimethyl sulfoxide (250 mL). Hydrogen peroxide (35%, 18.2 g, 187 mmol) was added dropwise to the mixture in 1 h through a syringe pump at room temperature using a water bath. Iron (II) sulfateheptahydrate (2 to 3 equivalent) was added to the reaction mixture in portions to keep the temperature between 25 C to 35 C, until the color of the reaction mixture is deep red. If TLC show the reaction not completed, then more hydrogen peroxide (2-3 equivalent) and more iron (II) sulfate heptahydrate (1-2 equivalent) were added in the same manner until the reaction is completed. After that time, the reaction mixture was partitioned between saturated sodium bicarbonate solution (200 mL) and ethyl acetate (400 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with saturated Sodium thiosulfate solution (50 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford a 78% yield (6.40 g) of 118b as a yellow oil: ]H NMR (500 MHz, CDC13) delta 6.23 (s, 1H), 4.23 (s, 2H), 3.94 (t, 2H, J = 6.5 Hz), 3.81 (s, 3H), 2.74 (t, 2H, J = 6.5 Hz), 2.00 (m, 2H), 1.83 (m, 2H); (APCI+) m/z 219.3 (M+H)

The synthetic route of 624-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 624-75-9, These common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, 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: Starting amine (5.0 mmol) was dissolved in dry diethyl ether (17 mL) and iodoacetonitrile (5.5 mmol, 919 mg) was added dropwise under cooling. The mixture was stirred at room temperature for 3-14 days, then precipitate was filtered off, washed with diethyl ether and dried in vacuo to give the corresponding quaternary ammonium salt 2. If the solid precipitate was not formed after 7 days, the mixture was evaporated under reduced pressure. The crude product was washed with diethyl ether (3 × 15mL) and dried in vacuo. The quaternary ammonium salt 2 was used in the next step without additional purification. The corresponding quaternary ammonium salt (3.0 mmol) was heated at 150 C on oil bath in freshly distilled DMF (7 mL) in a 25 mL round-bottom flask fitted with reflux condenser and CaCl2-tube for 15 minutes. The mixture was cooled to room temperature, diluted with H2O (20 mL) and extracted with PhMe (2 × 15mL). The organic phase then was washed with H2O (2 × 15mL) and brine (15 mL), dried over Na2SO4 and evaporated in vacuo to give the desired aminoacetonitrile 4. The latter, if necessary, was purified by column chromatography (it is convenient to visualize aminoacetonitriles on TLC-plate by treating with the diluted solution of ninhydrin in EtOH). Note, that aminoacetonitriles are moisture sensitive. Products after column chromatography were additionally dried by the addition of dry PhMe (5 mL) and evaporation in vacuo.

Statistics shows that 2-Iodoacetonitrile is playing an increasingly important role. we look forward to future research findings about 624-75-9.

Reference:
Article; Buev, Evgeny M.; Smorodina, Anastasia A.; Stepanov, Maxim A.; Moshkin, Vladimir S.; Sosnovskikh, Vyacheslav Y.; Tetrahedron Letters; vol. 59; 17; (2018); p. 1638 – 1641;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 624-75-9, 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. 624-75-9 name is 2-Iodoacetonitrile, 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.

General procedure: A solution of Et3B (0.5 mL, 1.0 M in EtOH, 0.5 mmol) was added over 2 h by syringe pump to a stirred mixture of the iodide 2, 4,or 5 (2.0 mmol) and olefin 1 (1 mmol) in EtOH-H2O (1:1, 10 mL) in the dark and open to air. After complete addition, the brown mixture was allowed to stir for 1 h at r.t. DBU (457 mg, 3 mmol) was added at 0 C, and the mixture was stirred at r.t. overnight. After addition of a sat. aq solution of NH4Cl (50 mL), the mixture was extracted with Et2O (20 and 10 mL), and the organic phases were washed with brine (10 mL). The combined organic layers were dried over Na2SO4 and concentrated. The crude product was purified by column chromatography.

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

Reference:
Article; Meyer, Daniel; Vin, Estelle; Wyler, Benjamin; Lapointe, Guillaume; Renaud, Philippe; Synlett; vol. 27; 5; (2016); p. 745 – 748;,
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. 624-75-9, name is 2-Iodoacetonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C2H2IN

General procedure: Individual solutions of secondary N-alpha-trimethylsilylmethyl-N-benzylamines19 (5mmol) in acetonitrile (100mL) containing K2CO3 (10mmol) and 2-iodoacetonitrile (4.5mmol) were stirred for 12hat room temperature and concentrated in vacuo to give residues that were partitioned between water and CH2Cl2. The CH2Cl2 layers were dried and concentrated in vacuo to afford residues that were subjected to silica gel column chromatography (EtOAc/hexane=1: 15 – 1: 30) to yield corresponding alpha-aminonitiriles 11a18 (91%), 11b (74%), 11c (78%), 11d (85%), 11e (75%), 11f (75%), 11g (74%), 11h (75%), 11i (78%), 11j (78%) and 11k (66%).

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; Lim, Suk Hyun; Cho, Dae Won; Choi, Jungkweon; An, Hyunjun; Shim, Jun Ho; Mariano, Patrick S.; Tetrahedron; vol. 73; 44; (2017); p. 6249 – 6261;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. Recommanded Product: 2-Iodoacetonitrile

The compound obtained in Example 21 (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 by heating. 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 to the residue were added 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 [4-(2-chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile and [4-(2-chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile as yellow oil. These two regioisomers (4.78 g, 92%) were used in the next reaction step without separation.[4-(2-Chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.29 (s, 3H), 3.71 (s, 3H), 5.19 (s, 2H), 6.73 (s, 1H), 6.75 (s, 1H), 6.85 (s, 1H), 7.06 (d, J=4.4 Hz, 1H), 7.26 (s, 1H), 7.79 (s, 1H), 8.24 (d, J=4.8 Hz, 1H); 13C NMR (CDCl3) delta 21.53, 39.97, 55.29, 110.91, 111.12, 113.65, 115.67, 118.75, 121.59, 121.65, 122.78, 130.58, 132.37, 140.16, 143.28, 149.68, 151.45, 151.79, 159.71, 162.33.[4-(2-Chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.39 (s, 3H), 3.83 (s, 3H), 4.94 (s, 2H), 6.63 (s, 1H), 6.74 (s, 1H), 6.92-6.96 (m, 2H), 7.19 (s, 1H), 7.93 (s, 1H), 8.17 (d, J=5.2 Hz, 1H); 13C NMR (CDCl3) delta 21.56, 37.78, 55.48, 112.15, 113.91, 117.08, 118.16, 119.88, 121.36, 122.48, 128.46, 139.57, 141.60, 142.19, 142.85, 149.78, 151.95, 160.48.To a solvent mixture of THF and water (4:1, 10 mL) were added the mixture prepared in Example 22 (100 mg, 0.30 mmol), phenylboronic acid (43.9 mg, 0.36 mmol), dichlorobis(triphenylphosphine)palladium (II) (11 mg, 0.02 mmol) and potassium carbonate (42 mg, 0.30 mmol), 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×3). 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, 1:3, v/v): (70 mg, 62%); m.p. 51-52 C.; 1H NMR (CDCl3) delta 2.41 (s, 3H), 3.81 (s, 3H), 4.95 (s, 2H), 6.76 (s, 1H), 6.82 (s, 1H), 6.95 (s, 1H), 7.06 (d, J=4.5 Hz, 1H), 7.41-7.44 (m, 3H), 7.58 (s, 1H), 7.80 (d, J=6.3 Hz, 2H), 8.01 (s, 1H), 8.53 (d, J=4.8 Hz, 1H) 13C NMR (CDCl3) delta 21.57, 37.76, 55.49, 112.31, 114.07, 116.90, 118.29, 119.60, 119.70, 122.75, 126.83, 128.71, 129.03, 129.11, 139.21, 139.61, 140.45, 141.47, 141.89, 149.88, 157.70, 160.51.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 624-75-9, its application will become more common.

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

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. SDS of cas: 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 (0.32 g, 0.95 mmol), 3-acetylphenylboronic acid (0.19 g, 1.13 mmol), dichlorobis(triphenylphosphine)palladium (II) (33 mg, 0.04 mmol) and potassium carbonate (0.13 g, 0.95 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×3). 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): (106 mg); m.p. 149-150 C.; 1H NMR (CDCl3) delta 2.37 (s, 3H), 2.67 (s, 3H), 3.78 (s, 3H), 4.95 (s, 2H), 6.71 (s, 1H), 6.77 (s, 1H), 6.87 (s, 1H), 7.51-7.70 (m, 3H), 7.92 (s, 1H), 7.97 (d, J=7.6 Hz, 1H), 8.16 (d, J=7.8 Hz, 1H), 8.53 (s, 1H), 8.57 (d, J=1.2 Hz, 1H); 13C NMR (CDCl3) delta 21.61, 26.82, 37.80, 55.41, 112.41, 114.22, 116.66, 118.39, 120.33, 122.71, 126.53, 126.96, 128.67, 129.04, 129.09, 131.18, 135.01, 137.58, 139.36, 139.48, 141.15, 141.36, 147.96, 154.21, 160.37, 198.06.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 624-75-9, its application will become more common.

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