Category: 17564-64-6

Electric Literature of 17564-64-6, Researchers are common within chemical engineering and are often tasked with creating and developing new chemical techniques, frequently combining other advanced and emerging scientific areas.

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. 7.1.55 2-((2-(2-(Pentan-2-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (3C) White powder, mp 125-126 C, 84% yield; 1H NMR (400 MHz, CDCl3): delta 0.92-0.95 (t, 3H, CH3), 1.59-1.61 (m, 2H, CH2), 1.93 (s, 3H, CH3), 2.23-2.27 (t, 2H, CH2), 3.83 (s, 2H, CH2, thiazolidinone), 5.73 (s, 2H, ArCH2), 7.75-7.76 (m, 2H, Ar), 7.86-7.87 (m, 2H, Ar). 13C NMR (100 MHz, CDCl3): delta 13.8, 14.0, 17.5, 19.6, 19.8, 22.9, 32.2, 34.1, 40.6, 45.0, 45.1, 123.6, 131.7, 134.3, 158.0, 166.7, 170.0, 171.1.

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.

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

Reference of 17564-64-6, 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.

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. 7.1.53 2-((2-(2-(Propan-2-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (1C) Yellow powder, mp 119-124 C, 99% yield; 1H NMR (400 MHz, DMSO-d6): delta 1.79 (s, 3H, CH3), 1.88 (s, 3H, CH3), 3.95 (s, 2H, CH2, thiazolidinone), 5.52 (s, 2H, ArCH2), 7.73-8.31 (m, 4H, Ar).

Statistics shows that 2-(Chloromethyl)isoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 17564-64-6.

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

17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C9H6ClNO2

To a stirred suspension of sodium hydride (60% in mineral oil, 2.4 g, 60.0 mmol) in anhydrous ether (170 mL) was added dropwise dimethyl isobutylmalonate (10.0 mL, 53.8 mmol) over 10 min. The resulting mixture was stirred at room temperature under a nitrogen atmosphere for 3 h, and was then chilled in an ice-bath. To the stirred cold solution was added N-(chloromethyl)phthalimide (10.1 g, 51.6 mmol) in one portion. The mixture was allowed to warm to room temperature slowly, and was stirred at room temperature for 18 h, followed by refluxing for 1 h. The reaction mixture was cooled to room temperature, and cold 1 N HCl (215 mL) was added. The organic phase was separated, and the aqueous phase was extracted with ether (40 mL). The combined organic phase was washed with brine (40 mL x 2), dried over MgSO4, and then concentrated on a rotary evaporator to dryness. The residue was triturated with hexanes (60 mL). The product was collected by filtration, washed with hexanes (30 mL x 2), and dried in vacuo to afford dimethyl 2-((l,3-dioxoisoindolin-2- yl)methyl)-2-isobutylmalonate as a white solid (15.3 g, yield 85%).1H NMR (CDCl3) delta (ppm) 7.84 (2H, q, J = 2.8 Hz), 7.72 (2H, q, J = 2.8 Hz), 4.30 (2H, s), 3.78 (6H, s), 2.02 (IH, m), 1.80 (2H, d, J = 6.4 Hz), 0.86 (6H, d, J = 6.8 Hz).

The synthetic route of 17564-64-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PONIARD PHARMACEUTICALS, INC.; WO2009/139834; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature 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.

NONOate salt NS-01 (0.270 g, 1.58 mmol) suspended in acetonitrile (3.0 mL) was treated with a solution of N-(chloromethyl)phthalimide (0.280 g, 1.43 mmol) in acetonitrile (3.0 mL) and then sodium iodide (0.215 g, 1.43 mmol) was added. The resulting mixture was stirred at 25 C overnight. N,N-dimethylformamide (1.0 mL) was added to the reaction mixture which was then heated to 60 C for 1 hour. The acetonitrile was removed under reduced pressure. The residue was suspended in ethyl acetate and then washed with a 0.2 N solution of sodium thiosulfate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was subjected to prep-chromatography using ethyl acetate in hexane to provide a tan oily solid (14 mg, 3.0% yield). 1H NMR (400 MHz, CDCI3) delta 7.92-7.87 (m, 2H), 7.78-7.73 (m, 2H), 5.67 (s, 2H), 2.97 (s, 1H), 2.19 (s, 2H), 1.59 (s, 6H). LC tr=2.65 minutes (C-18 column, 5 to 95% acetonitrile/water over 6 minutes at 1.7 mL/min with detection 254 nm, at 23 C). ES(pos)MS m/z 331 (M+Na calcd for C13H16N4O5 requires 331).

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:
Patent; SARMONT LLC; MARTINEZ, Eduardo J.; TALLEY, John J.; JEROME, Kevin D.; BOEHM, Terri L.; WO2015/108835; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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., name: 2-(Chloromethyl)isoindoline-1,3-dione

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 (1M 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 chromatography (silica, EtOAc/Petroleum ether elution). Product fractions were combined and concentrated in vacuo and the residue recrystallized from EtOAc to give the product as a white solid (7.56 g, 23 %).

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; MERCK PATENT GMBH; VERTEX PHARMACEUTICALS INCORPORATED; BLEICH, Matthew; CHARRIER, Jean-Damien; DONG, Huijun; DURRANT, Steven; ENO, Meredith Suzanne; ETXEBARRIA I JARDI, Gorka; EVERITT, Simon; FRAYSSE, Damien; KNEGTEL, Ronald; MOCHALKIN, Igor; NORTH, Kiri; PORICHIS, Filippos; PULLIN, Robert; QIU, Hui; STORCK, Pierre-Henri; TWIN, Heather Clare; XIAO, Yufang; (312 pag.)WO2019/148136; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route 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: 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. 7.1.59 2-((2-(2-(Heptan-2-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (7C) Grey powder, mp 84-85 C, 85% yield; 1H NMR (400 MHz, DMSO-d6): delta 1.19-1.29 (m, 8H, CH2), 1.92 (s, 3H, CH3), 2.20-2.28 (t, 3H, CH3), 3.78 (s, 2H, CH2, thiazolidinone), 5.53 (s, 2H, ArCH2), 7.88-7.89 (m, 4H, Ar).

The synthetic route of 17564-64-6 has been constantly updated, and we look forward to future research findings.

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

Related Products of 17564-64-6, 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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a cold (0 C.) solution of N-(chloromethyl)phthalimide (40.0 g, 205.0 mmol) in acetone (400 mL) there is added, in successive portions, potassium O-ethylxanthate (36.1 g, 225.0 mmol). The reaction mixture is stirred at 0 C. for 30 minutes and then the solvent is evaporated off. The residue thereby obtained is taken up in water. The aqueous phase is extracted with dichloromethane, whilst the organic phases are dried over MgSO4 and concentrated under reduced pressure. The residue thereby obtained is recrystallised from a mixture of ethyl acetate and petroleum ether to yield the title product in a yield of 74%. 1H NMR (delta, ppm) 7.90-7.84 (m, 2H, CH-2), 7.77-7.72 (m, 2H, CH-1), 5.33 (s, 2H, (CDCl3, 400 MHz) CH2-5), 4.68 (q, 2H, J=7.1 Hz, CH2-7), 1.46 (t, 3H, J=7.1 Hz, CH3-8).

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

Reference:
Patent; LES LABORATOIRES SERVIER; Zard, Samir; Sire, Beatrice; Boumediene, Mehdi; US2013/289308; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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., category: indolines-derivatives

To a stirred suspension of sodium hydride (60% dispersion in mineral oil, 0.997 g, 24.9 mmol) in diethyl ether (100 mL) was added dimethyl 2- isobutylmalonate (3.13 g, 16.6 mmol) dropwise. The resulting mixture was stirred at RT for 3 h. The reaction mixture was cooled to 0 C. N-chloromethyl phthalimide (3.24 g, 16.6 mmol) was added in one portion. The reaction mixture was stirred at RT overnight followed by heating to reflux for 1 h. The reaction mixture was cooled to RT and cold 1.5 N HC1 (100 mL) was added. The organic layer was separated. The aqueous layer was extracted with diethyl ether (2 x 50 mL). The combined ether layers were dried over Na2S04, filtered and concentrated under reduced pressure to afford the title compound (5.3 g, 15.2 mmol, 92 % yield). The crude product was taken to next step without further purification. LCMS (ESI) m/e 347.9 [(M+H)+, calcd for Ci8H22N06, 348.1]; LC/MS retention time (method C): tR = 1.95 min.

The synthetic route of 17564-64-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DZIERBA, Carolyn Diane; BRONSON, Joanne J.; MACOR, John E.; DASGUPTA, Bireshwar; NARA, Susheel Jethanand; VRUDHULA, Vivekananda M.; PAN, Senliang; HARTZ, Richard A.; RAJAMANI, Ramkumar; (199 pag.)WO2016/22312; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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., HPLC of Formula: C9H6ClNO2

EXAMPLE 1 N-(3,5-di-tert-butyl-4-hydroxyphenylthiomethyl)phthalimide A vessel was charged with 12.19 grams of 3,5-di-tert-butyl-4-hydroxybenzene thiol and 3.30 grams of potassium hydroxide dissolved in 50 ml of acetone and 2 ml of water at 0 C. which was mixed with 10.0 grams of N-(chloromethyl)phthalimide. After stirring for one hour, the precipitated product was removed by filtration and then recrystallized from ethyl acetate-hexane to give 14.9 grams of produt, m.p. 151-53 C. Anal. Calc’d for C23 H27 NO3 S: C, 69.5; H, 6.9; N, 3.5. Found: C, 69.5, H, 7.0, N, 3.6.

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.

Reference:
Patent; Ciba-Geigy Corporation; US4692532; (1987); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route 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.

Butanethiol (902 mg, 10 mmol), carbon disulfide (761 mg, 10 mmol), and THF (5 mL) were placed in 25 mL round-bottomed flask. A solution of KOH (561 mg, 10 mol) in 3 mL of water was added dropwise under stirring at room temperature. The resulting solution was stirred at room temperature for a further 15 min. Then the solution was added slowly into a solution of N-(chloromethyl)phthalimide (1.96 g, 10 mmol) in acetone (10 mL). The reaction mixture was stirred for 30 min. After removal of the solvent, the residue was diluted with ethyl acetate (100 mL). The solution was washed sequentially with water (2*50 mL) and saturated brine (2*50 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation, the residue was recrystallized from a mixture of petroleum ether and ethyl acetate to give S-[(1-tert-butoxycarbonylamino-4-phthalimido)butan-2-yl] S’-butyl trithiocarbonate (1k) as yellow crystals 2.86 g, 88% yield, mp: 89-91 C. Lit. 17 89-91 C. 1H NMR (CDCl3, 400 MHz) (delta, ppm) 0.93 (t, J=7.2 Hz, 3H, CH3), 1.42 (hextet, J=7.2 Hz, 2H, CH2), 1.64-1.72 (m, 2H, CH2), 3.37 (t, J=7.2 Hz, 2H, CH2), 5.65 (s, 2H, CH2), 7.75 (dd, J=5.2, 3.0 Hz, 2H, ArH), 7.87 (dd, J=5.2, 3.0 Hz, 2H, ArH). 13C NMR (CDCl3, 101 MHz) (delta, ppm) 13.5, 22.0, 29.8, 36.9, 41.9, 123.7, 131.8, 134.4, 166.6, 220.8.

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.

Reference:
Article; Huang, Zhongyan; Xu, Jiaxi; Tetrahedron; vol. 69; 48; (2013); p. 10272 – 10278;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem