Category: 5332-26-3

Related Products of 5332-26-3, A common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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.

A mixture of 1.02 g (7.4 mmol) of freshly calcined K2CO3, 7.0 mmol of the corresponding 2-thiouracil 1-3 and 7.7 mmol of 2-(bromomethyl)-2Hisoindole-1,3-dione in 20 mL of anhydrous DMF was stirred at room temperature for 72 h. The mixture was filtered, the fi ltrate was evaporated to dryness under reduced pressure. The precipitate of mineral salts on the filter was dissolved in 1 M. aqueous H3PO4 and the resulting solution was combined with the bottom residue. The resulting mixture was filtered. The filtercake was washed with water, and then the filtrate was extracted EtOAc (3¡Á50 mL). The filter cake was air dried to constant weight, and the organic extract was dried over anhydrous MgSO4. The dried organic extract was evaporated to dryness under reduced pressure. The residue was mixed with the filter cake and evaporated in a mixture with toluene (3¡Á50 mL) under reduced pressure. A crude product was obtained in the residue, which was subjected to further purification using preparative HPLC. 2-{[(6-Methyl-4-oxo-1,2-dihydropyrimidin-2-yl)-sulfanyl]methyl}-2H-isoindole-1,3-dione (4). Yield 63%, mp 251.5252.1C, Rf 0.38 (EtOAc – hexane, 2 : 1). IR spectrum (mineral oil), nu, cm-1: 3006, 1778, 1719,1574, 1540, 1464, 1292, 708. 1H NMR spectrum (400 MHz), delta, ppm: 2.07 s (3H, 3), 5.42 s (2, S2),6.06 s (1, ), 7.86-7.93 m (4Ar), 12.44 s (1, N).Mass spectrum, m/z (I, %): 302.3 (100) [M + H]+. Found,%: C 56.01; H 3.72; N 14.08; S 10.51. C14H11N3O3S.Calculated, %: C 55.80; H 3.68; N 13.95; S 10.64.

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Babushkin, A. S.; Chapurkin, V. V.; Maryshev, A. Yu.; Navrotskii, M. B.; Novakov, I. A.; Ruchko, E. A.; Schols, D.; Sheikin, D. S.; Russian Journal of General Chemistry; vol. 90; 3; (2020); p. 352 – 356; Zh. Obshch. Khim.; vol. 90; 3; (2020); p. 365 – 370,6;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 5332-26-3, These common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)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 vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

Statistics shows that 2-(Bromomethyl)isoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 5332-26-3.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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. Application In Synthesis of 2-(Bromomethyl)isoindoline-1,3-dione

(S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-(1,3-dioxo-1,3-dihydro-isoindole-2-ylmethoxycarbonyl)-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinate To a mixture of No. 5447725 (Compound G; 40 mg, 0.07 mmol), DBU (26 muL, 0.171 mmol), and dichloromethane (0.57 mL) was added 2-bromomethyl-isoindole-1,3-dione (41 mg, 0.171 mmol) commercially available from Aldrich (cat. No. 252611-5G). After the mixture was stirred at room temperature for 17 hours, further 2-bromomethyl-isoindole-1,3-dione (41 mg, 0.171 mmol) and DBU (9 muL, 0.057 mmol) were added. After further 2 hours, the reaction solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4-(1,3-dioxo-1,3-dihydro-isoindole-2-ylmethyl) 1-butyl (S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-(1,3-dioxo-1,3-dihydro-isoindole-2-ylmethoxycarbonyl)-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinate (51 mg, 89%; ESI (LC/MS positive mode) m/z 1018 (M+H); Rt 3.40 min.).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5332-26-3, its application will become more common.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; KOHCHI, Yasunori; NAKAMA, Kimitaka; KOMIYAMA, Susumu; WATANABE, Fumio; EP2886530; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 5332-26-3, 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. 5332-26-3 name is 2-(Bromomethyl)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 vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

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

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5332-26-3, name is 2-(Bromomethyl)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 5332-26-3, Recommanded Product: 5332-26-3

To a solution of N-(bromomethyl)phthalimide (2.0 g, 8.3 mmol) in CH2Cl2 (15 mL) was added sodium azide (1.62 g, 24.9 mmol), tetrabutylammonium iodide (0.10 g, 0.33 mmol) and H2O (3 mL). The reaction mixture was heated at reflux for 24 h. The mixture was cooled at room temperature, CH2Cl2 (5 mL) was added and the organic phase was washed and dried over Na2SO4, the solvent was removed in vacuo and the product was purified by crystallisation to afford a yellow solid (1.6 g, 95%); m.p. 39-40 C (lit. 37-39 C);21 FTIR (ATR, cm-1): 3474, 2962, 2872, 2129, 1776, 1712, 1610; 1H NMR (300 MHz, CDCl3) delta 7.94 (dd, J = 5.5, 3.1 Hz, 2H), 7.80 (dd, J = 5.5, 3.1 Hz, 2H), 5.08 (s, 2H); 13C NMR (75 MHz, CDCl3) delta 167.1 (2 ¡Á C), 134.6 (2 ¡Á CH), 131.7 (2 ¡Á C), 123.9 (2 ¡Á CH), 52.2 (CH2); MS [EI+] m/z (%): 202 [M]+ (5), 173 [M – HN2]+ (10), 161 [C8H5N2O2] (10), 159 [M – HN3]+ (40), 147 [C8H5NO2] (10), 133 [C8H5O2] (60), 104 [C7H4O] (100).

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

Reference:
Article; Lopez-Gonzalez, Ricardo; Bautista-Renedo, Joanatan; Martinez-Otero, Diego; Reyes, Horacio; Gonzalez-Rivas, Nelly; Cuevas-Yanez, Erick; Journal of Chemical Research; vol. 40; 5; (2016); p. 308 – 313;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 5332-26-3, A common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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 vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 5332-26-3, These common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)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: Benzimidazole (1 mmol) and potassium hydroxide (1 mmol) were dissolved in ethyl alcohol (60 mL). The alkyl halide (1 mmol) was slowly added after the obtained reaction mixture was stirred at room temperature for 1 h. The solution was refluxed for 6 h, cooled to roomtemperature and the precipitated potassium chloride was removed by filtration. The solvent was removed by distillation. The product was then crystallized, washed several times with diethyl ether and then dried in vacuo. To a solution of 1-alkylbenzimidazole (1 mmol) in dried DMF (4 mL), alkyl halide (1 mmol) was added slowly and the reaction mixture was stirred at 80 C for 24 h under argon. After completion of the reaction, the DMF was removed by vacuum and diethyl ether (15 mL) was added to the mixture. The solid was washed with diethyl ether (2 ¡Á 15 mL) and dried under vacuum. The product was crystallized in an ethanol/diethyl ether mixture (3:1) at room temperature. The purified compounds were obtained as white or cream solids. Their structures were characterized by NMR (1H and 13C), FTIR, ESI-FTICR-MS (for 2 and 4) spectroscopic methods and elemental analysis

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Akkoc, Senem; Goek, Yetkin; Ilhan, Ilhan Oezer; Kayser, Veysel; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 81 – 88;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 5332-26-3, 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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

A suspension of N-(bromomethyl)phthalimide (3.6g, 15.0mmol) in triethylphosphite (3.00g, 18.0mmol) was heated to 90Cfor 3h. A distillation apparatus was then installed and volatile ethyl bromide was removed by reduced pressure distillation. The crude mixture was cooled to room temperature, and the resulting white solid was used without further purification. 1H NMR (300MHz, CDCl3) delta=1.24 (t, J=7.1Hz, 6H, 2¡ÁCH3), 4.01 (d, 2JH-P=11.4Hz, 2H, 1¡ÁCH2), 4.12 (m, 4H, 2¡ÁCH2), 7.73 (dd, J=5.5, 3.1Hz, 2H, 2¡ÁCH), 7.86 (dd, J=5.3, 3.0Hz, 2H, 2¡ÁCH) ppm. To a solution of this solid (4.5g, 15mmol) in ethanol (20mL) was added hydrazine monohydrate (1.05mL, 21.6mmol) and the resulting mixture was stirred at room temperature overnight, and then refluxed for 3h. The crude mixture was cooled down to 0C, and the white precipitate was removed by filtration and washed with ice-cold ethanol. The solution was concentrated under vacuum, and the resulting oily residue was purified by column chromatography on silica gel eluting with a gradient of Et2O/ MeOH (80:20?70:30) to afford compound 24 as a pale yellow oil (2.43g, 97%). TLC: Rf=0.30 (silica gel, Et2O/MeOH 80:20, stained with ninhydrin). 1H NMR (300MHz, CD3CN) delta=1.31 (t, J=7.1Hz, 6H, 2¡ÁCH3), 1.76 (br, 2H, NH2), 2.94 (d, 2JH-P=10.6Hz, 2H, 1¡ÁCH2), 4.08 (quintet, 3JH-H=3JH-P=7.0Hz, 2H, 1¡ÁCH2), 4.10 (quintet, 3JH-H=3JH-P=7.1Hz, 2H, 1¡ÁCH2) ppm. 31P NMR (121MHz, CDCl3) delta=27.49ppm.

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

Reference:
Article; Leygue, Nadine; Perez e Iniguez De Heredia, Aritz; Galaup, Chantal; Benoist, Eric; Lamarque, Laurent; Picard, Claude; Tetrahedron; vol. 74; 31; (2018); p. 4272 – 4287;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 5332-26-3 as follows. Recommanded Product: 5332-26-3

General procedure: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

According to the analysis of related databases, 5332-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 5332-26-3, A common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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.

(3a) To a THF (20 mL) solution of dimethyl methylmalonate (5.5 g, 37 mmol) at -10 C. was added NaH (60% in mineral oil, 1.66 g, 1.1 eq). The mixture was stirred for 20 min, then N-bromomethylphthalimide (9.5 g, 1.05 eq) was added at 0 C. The mixture was allowed to slowly warm to rt, stirred for 3 h, and quenched with water. Following extraction with ethyl acetate, the combined ethyl acetate extracts were washed with 1 N HCl and brine, dried (MgSO4), filtered and concentrated. Purification by flash column chromatography (20% ethyl acetate-hexane) yielded the phthalimide as a white crystalline solid (5.81 g, 51%).

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Duan, Jingwu; Jiang, Bin; Chen, Lihua; Lu, Zhonghui; Barbosa, Joseph; Pitts, William J.; US2003/229084; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem