17564-64-6 Archives - Page 4 of 4 - Indolines-derivatives

Some tips on 17564-64-6

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.

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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Product Details of 17564-64-6

(Bis(trimethylsilyl)amino)lithium (2.4 mL of a 1 M solution in THF, 2.4 mmol) was added dropwise to a solution of benzyl 3,3-dimethyl-4-oxo-piperidine-1-carboxylate (500 mg, 2 mmol) in THF (7 mL) at -78 C under N2. After 90 minutes, a solution of 2- (chloromethyl)isoindoline-1,3-dione (560 mg, 3 mmol) in THF (2 mL) was added. The reaction mixture was stirred for 1 hour then quenched by the addition of saturated aqueous NH4Cl solution (~2 mL). The reaction mixture was diluted with EtOAc, washed with a saturated aqueous sodium bicarbonate solution and brine. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica, PE/EtOAc gradient elution) and then by reverse phase chromatography (C18, MeCN / water- 0.1% ammonium hydroxide as eluent) to give benzyl 5-[(1,3-dioxoisoindolin-2-yl)methyl]-3,3-dimethyl-4-oxo-piperidine-1- carboxylate as a colourless oil (180 mg, 21%); MS m/z: 421 (M+H)+.

Reference:
Patent; MERCK PATENT GMBH; VERTEX PHARMACEUTICALS INCORPORATED; BAYLY, Andrew; BLEICH, Matthew; CHARRIER, Jean-Damien; DODD, James; DURRANT, Steven; ENO, Meredith Suzanne; ETXEBARRIA I JARDI, Gorka; EVERITT, Simon; FRAYSSE, Damien; KELLY, Shazia; KNEGTEL, Ronald; MOCHALKIN, Igor; MORTIMORE, Michael; NORTH, Kiri; PORICHIS, Filippos; PULLIN, Robert; RUTHERFORD, Alistair; STORCK, Pierre-Henri; TWIN, Heather Clare; XIAO, Yufang; (1159 pag.)WO2019/148132; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Brief introduction of 17564-64-6

The synthetic route of 2-(Chloromethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

These common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, 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. Computed Properties of C9H6ClNO2

The N,Se acetal 5 was prepared by a slight and safer modification of the original procedure4 where, the required phenylselenol intermediate was replaced by sodium phenylselenolate. In a 50 mL three-neck flask equipped with a reflux condenser were placed diphenyl diselenide (0.63 g, 2 mmol) and 16 mL of dry DMF. The solution was heated at 60 C and stirred rapidly under nitrogen while NaBH4 (0.15 g, 4 mmol) was added portionwise. Hydrogen was evolved and the reaction mixture turned colorless and homogeneous upon complete reduction of the selenide. The reaction was heated at 110 C for 1 h and then cooled to room temperature. Solid N-chloromethylphthalimide (0.78 g, 4 mmol) was added to the orange solution. After stirring at room temperature for 12 h, 2 N aqueous hydrochloric acid (10 mL) was added carefully to the white suspension. The entire product mixture was poured into 50 mL of water and 40 mL of diethyl ether, mixed, and separated. The aqueous phase was extracted with 20 mL of diethyl ether and the combined organic phases were washed with H2O (4 ¡Á 10 mL), 10 mL of brine, dried over sodium sulfate and concentrated. The solid residue was washed with light petroleum (2 ¡Á 10 mL) and dried over P2O5 to afford 5 in 82% yield and with spectral data in good agreement with those reported in the literature.4

The synthetic route of 2-(Chloromethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Temperini, Andrea; Minuti, Lucio; Tetrahedron Letters; vol. 53; 22; (2012); p. 2709 – 2711;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

The origin of a common compound about 17564-64-6

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 17564-64-6.

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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., name: 2-(Chloromethyl)isoindoline-1,3-dione

EXAMPLE 42 To a stirred solution containing 15 grams (0.12 mole) of amine, 19.2 grams (0.12 mole) of 25% sodium hydroxide and 250 ml. of acetone there was added dropwise at 5-15 C., 9.2 grams (0.12 mole) of carbon bisulfide. After stirring at 25-30 C. for an hour, 19.6 grams (0.1 mole) of phthalimidomethyl chloride was added in one portion and stirring continued at 25-30 C. for another hour. Thereupon there was added 700 ml. of water and the reaction mixture stirred and cooled to 5 C. The product was isolated as described in Example 41. Phthalimidomethyl 3-azabicyclo[3.2.2]nonane-3- carbodithioate was obtained in 99% yield as a grey solid melting at 139-140 C. after recrystallization from ethyl alcohol/benzene. Analysis gave 7.46% nitrogen and 18.09% sulfur compared to 7.77% nitrogen and 17.79% sulfur calculated for C18 H20 N2 O2 S2.

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 17564-64-6.

Reference:
Patent; Monsanto Company; US4013638; (1977); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some scientific research about 17564-64-6

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Chloromethyl)isoindoline-1,3-dione, its application will become more common.

Application of 17564-64-6,Some common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, molecular formula is C9H6ClNO2, 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 solution of ammonium O,O-(2-methylpentane-2,4-diyl) dithiophosphate (1) (0.01 mol) was dissolved in absolute methanol (20 mL) and treated with N-(chloromethyl)phthalimide (0.01 mol). The mixture was reuxed for 1 h, fltered and concentrated by distillation under reduced pressure.The resulting concentrated solution crystallized at room temperature. The white solid was fltered, washed with diethylether and dried over P2O5. It was recrystallized with aMeOH:CHCl3 (9:1) mixture.

Reference:
Article; Rastogi, Rupali; Gupta, Srasti; Tarannum, Nazia; Agarwal, Ranu; Butcher; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 192; 3; (2017); p. 300 – 306;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 17564-64-6

According to the analysis of related databases, 17564-64-6, the application of this compound in the production field has become more and more popular.

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 17564-64-6 as follows. Application In Synthesis of 2-(Chloromethyl)isoindoline-1,3-dione

A solution of ammonium O,O-(2-methylpentane-2,4-diyl) dithiophosphate (1) (0.01 mol) was dissolved in absolute methanol (20 mL) and treated with N-(chloromethyl)phthalimide (0.01 mol). The mixture was reuxed for 1 h, fltered and concentrated by distillation under reduced pressure.The resulting concentrated solution crystallized at room temperature. The white solid was fltered, washed with diethylether and dried over P2O5. It was recrystallized with aMeOH:CHCl3 (9:1) mixture. Color: white; yield: 75-80%,m.p. 66C. Anal. found C 48.98; H 4.82; N 3.93; S 17.51%.Calcd. for C15H18NO4PS2 (371.42): C 48.51; H 4.88; N 3.77; S17.27%; IR, flm nu(cm-1): = 1719 (C=O); 526 (P-S); 719 (P=S);1120 [(P)-O-C]; 967 [P-O-(C)]; 1H NMR: delta = 7.96 (m, 4H,Har); 4.99 (s, 2H, OCH2), 2.51 (s, 1H, OCH), 1.95 (s, 1H, CH),1.5 (m, 3H, CH3), 1.20 (m, 2H, CH2), 1.14 (m, 3H, CH3); 13CNMR: delta = 167.4 (C=O); 135.0 (C2); 131.5 (C3), 123.5 (C4); 86.9(N-CH2); 60.1 (OCH2); 72.6 (OCH); 128.3 (CH); 27.0 (CH3);31.5 (CH2); 21.6 (CH3), 31P NMR: delta = 82.9.

According to the analysis of related databases, 17564-64-6, the application of this compound in the production field has become more and more popular.

Some tips on 17564-64-6

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Chloromethyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Application of 17564-64-6, 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. 17564-64-6 name is 2-(Chloromethyl)isoindoline-1,3-dione, 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: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. 7.1.63 2-((2-(2-(2-Methylcyclopentylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (11C) White powder, mp 158-162 C, 83% yield; 1H NMR (400 MHz, CDCl3): delta 1.14-1.17 (d, J = 10 Hz, 3H, CH3), 1.28-1.31 (m, 2H, cyclopentane), 1.83 (bs, 1H, cyclopentane), 1.98-2.02 (m, 1H, cyclopentane), 2.25-2.30 (m, 1H, cyclopentane), 2.48-2.54 (m, 2H, cyclopentane), 3.83 (s, 2H, CH2, thiazolidinone), 5.71 (s, 2H, ArCH2), 7.76-7.77 (m, 2H, Ar), 7.86-7.88 (m, 2H, Ar). 13C NMR (100 MHz, CDCl3): delta 16.9, 22.5, 30.3, 32.5, 33.7, 39.6, 45.1, 123.6, 131.7, 134.3, 157.9, 166.7, 171.0, 182.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Chloromethyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Article; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Introduction of a new synthetic route about 17564-64-6

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Adding a certain compound to certain chemical reactions, such as: 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, belongs to indolines-derivatives 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 17564-64-6, COA of Formula: C9H6ClNO2

A solution of benzyl (2S,5S)-2,5-dimethyl-4-oxo-piperidine-1-carboxylate (46.3 g, 177.2 mmol) in THF (280 mL) was cooled to -78 C before LiHMDS (1 M in THF) (212 mL of 1 M, 212 mmol) was added at such a rate as to keep the temperature below -65 C. On complete addition, the mixture was stirred at -78 C for a further 10 minutes before a solution of 2- (chloromethyl)isoindoline-1,3-dione (41.6 g, 213 mmol) in THF (230 mL) was added at such a rate as to keep the temperature below -65 C. On complete addition, the dry ice/acetone cooling bath was removed and the reaction flask was placed in an ice/water bath. The reaction mixture was allowed to warm to 0 C over 30 minutes. The mixture was re-cooled to -78 C before being quenched carefully with saturated aqueous NH4Cl solution (93 mL) at such a rate as to keep the internal temp below -65 C. On complete addition the cooling bath was removed and the mixture allowed to warm to ambient temperature. EtOAc (500 mL) was added and the organic phase separated. The organic phase was washed with water (x 2), brine, dried (MgSO4), filtered and concentrated in vacuo. IPA (500 mL) was added to the residue and the resulting solution left to stand over the weekend. The resulting crystallised solid was collected by filtration, washed with minimal IPA and dried under vacuum to give benzyl (2S,3S,5S)-3-[(1,3-dioxoisoindolin-2- yl)methyl]-2,5-dimethyl-4-oxo-piperidine-1-carboxylate (31 g, 42%) as a colourless solid; 1H NMR (400 MHz, DMSO-d6) delta 7.95 – 7.78 (m, 5H), 7.49 – 7.24 (m, 6H), 5.25 – 5.07 (m, 2H), 4.73 – 4.53 (m, 1H), 4.33 (t, 1H), 3.95 – 3.75 (m, 2H), 3.01 (s, 2H), 2.70 – 2.57 (m, 1H), 1.11 (d, 3H), 0.88 (d, 3H); MS m/z: 421 (M+H)+.

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Extended knowledge of 17564-64-6

The chemical industry reduces the impact on the environment during synthesis 2-(Chloromethyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Electric Literature of 17564-64-6, 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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

Benzyl 3-methyl-4-oxo-piperidine-1-carboxylate (20 g, 0.08 mol) was dissolved in THF (300 mL) under N2. The solution was cooled to -78 C and LiHMDS (1 M in THF, 101.1 mL, 0.1 mol) was added dropwise over 20 minutes, keeping the temperature below -70 C. After stirring at -78 C for 90 minutes, a solution of 2-(chloromethyl)isoindoline-1,3-dione (23.7 g, 0.12 mol) in THF (200 mL) was added dropwise over 25 minutes, keeping the temperature below -70 C. The reaction was stirred at -78 C for 1 hour then quenched at -78 C by the addition of saturated aqueous ammonium chloride solution (65 mL) and the mixture allowed to warm to ambient temperature. The reaction was repeated and the two mixtures obtained were combined and extracted with EtOAc (300 mL). The organic phase was washed with saturated aqueous sodium bicarbonate solution (300 mL) and brine (300 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica, EtOAc/PE elution). The product fractions were combined and concentrated in vacuo and the residue recrystallized from EtOAc to give benzyl 3-((1,3-dioxoisoindolin-2-yl)methyl)-5-methyl-4- oxopiperidine-1-carboxylate as a white solid (7.56 g, 23%).

The chemical industry reduces the impact on the environment during synthesis 2-(Chloromethyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Extended knowledge of 17564-64-6

The synthetic route of 2-(Chloromethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

General procedure: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. 7.1.61 2-((2-(2-(Octan-2-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (9C) Brown powder, mp 65-70 C, 81% yield; 1H NMR (400 MHz, CDCl3): delta 0.89-0.91 (m, 4H, CH2, 3H, CH3), 1.53-1.62 (m, 3H, CH2), 1.93 (s, 3H, CH3), 2.24-2.35 (m, 2H, CH2), 2.44-2.47 (m, 1H, CH2), 3.83 (s, 2H, CH2, thiazolidinone), 5.72 (s, 2H, ArCH2), 7.70-76 (m, 2H, Ar), 7.86-7.88 (m, 2H, Ar).

The synthetic route of 2-(Chloromethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Simple exploration of 17564-64-6

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.

General procedure: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. 7.1.56 2-((2-(2-(Pentan-3-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (4C) White powder, mp 155-156 C, 89% yield; 1H NMR (400 MHz, CDCl3): delta 0.87-0.91 (t, 3H, CH3), 1.09-1.12 (t, 3H, CH3), 2.28-2.34 (q, 2H, CH2), 2.38-2.44 (q, 2H, CH2), 3.83 (s, 2H, CH2, thiazolidinone), 5.73 (s, 2H, ArCH2), 7.74-7.76 (m, 2H, Ar), 7.86-7.88 (m, 2H, Ar).

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.