5181-35-1 Archives - Indolines-derivatives

9/27/2021 News Our Top Choice Compound: 5181-35-1

Academic researchers, R&D teams, teachers, students, policy makers and the media all rely on us to share knowledge that is reliable, accurate and cutting-edge. Application of 5181-35-1

To a solution of 4-tertiary-butyl-dimethyl-silanyloxy methyl- 2H- l,2,3-triazol (40 g, 187 mmol, prepared according to the procedure described in US20150266867) in dimethylformamide (200 ml) was added potassium carbonate (28.4 g, 205 mmol) under stirring. After completion of 15 minutes of stirring a solution of 2-(2-bromoethoxy)- lH-isoindole- l,3(2H)- dione (50.5 g, 187 mmol, prepared according to the procedure described in PCT Int. Appl. 2000018790) was added. Continued stirring with continuous monitoring of the reaction. The progress of reaction was monitored by TLC (hexane: ethyl acetate, 5:5). After complete consumption of starting material the reaction mixture was filtered through celite bed to remove insolubles and filtrate was concentrated. The concentrated mass was added to water (400 ml) and extracted with ethyl acetate (2x 400 ml). The organic extracts were combined and washed with brine (200 ml), dried over anhydrous sodium sulphate. The volatiles were removed under reduced pressure yielded 67 g crude compound. The isomers were separated by column chromatography (100-200 mesh size silica gel) using hexane: ethyl acetate, 8:2 as an eluent. The non-polar isomer 2-{2-[4-(tertiary-butyl-dimethyl-silanyloxy methyl)-2H- l,2,3-triazol-2-yl]ethoxy}- lH-isoindole- l,3(2H)-dione was eluted at 12% ethyl acetate in hexane and yielded 24 g of the product. The mixture of polar isomers 2-{2-[4-(tertiary-butyl-dimethyl-silanyloxymethyl)- lH- l,2,3-triazol- l- yl]ethoxy}- lH-isoindole- l,3(2H)-dione and 2- {2-[5-(tertiary-butyl-dimethyl-silanyloxymethyl)- lH- l,2,3-triazol- l-yl]ethoxy}- lH-isoindole- l,3(2H)-dione was eluted at 45% ethyl acetate in hexane to obtain 12 g of the product.

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Reference:
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

9/3/2021 News Sources of common compounds: 5181-35-1

Adding a certain compound to certain chemical reactions, such as: 5181-35-1, name is 2-(2-Bromoethoxy)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 5181-35-1, Formula: C10H8BrNO3

(2) to 120mmol of compound III in 10mL of glacial acetic acid solution was added 15mL of 48% by weight of hydrobromic acid, stirred at 130 C for 5 minutes, cooled, filtered, the filtrate was concentrated to give a yellow compound IV

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.

Reference:
Patent; Nanjing Tech University; Hu Xuhong; Li Song; (13 pag.)CN109678810; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2-Sep-21 News The important role of 5181-35-1

Reference of 5181-35-1, 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. 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-(2-bromoethoxy)isoindoline- l,3-dione (20 g, 74 mmol, prepared according to the procedure described in step 1 of preparation 38), (lH-tetrazol- 5-ylmethyl)-carbamic acid tert-butyX ester (7.66 g, 74 mmol, prepared as per procedure described in step 2 of preparation 19) in dimethylformamide (100 ml) was added cesium carbonate (24.13 g, 74 mmol) lot wise under stirring at 25 C. After 16 hours, the reaction mixture was filtered and filtrate was slowly poured into chilled water (700 ml) and stirred for 30 minutes. The precipitated compound was filtered and washed with water (100 ml). The solid compound was dried at 35C for 2 hours under high vacuum, to provide 16 g of tert-butyX [(2-{2-[(l,3-dioxo- l,3-dihydro-2H- isoindol-2-yl)oxy]ethyl}-2H-tetrazol-5-yl)methyl] carbamate in 55% yield. Analysis: Mass: 389.4 (M+l); for Molecular weight: 388 and Molecular formula: Ci7H20N6O5.

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

Simple exploration of 5181-35-1

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. 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H8BrNO3

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 5181-35-1.

New downstream synthetic route of C10H8BrNO3

Reference of 5181-35-1,Some common heterocyclic compound, 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, molecular formula is C10H8BrNO3, 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.

To a clean dry flask containing suspension of 2-(2-bromoethoxy)isoindoline- l,3-dione (30 g, 0.111 mol), 1H- 1,2,3 triazole (7.66 g, 111 mmol) in dimethylformamide (150 ml) was added cesium carbonate ((36 g, 111 mmol) portion wise at room temperature under stirring. After 17 hours, the reaction mixture was filtered and filtrate was slowly poured into chilled water (1050 ml) under stirring. After 30 minutes of stirring, the separated precipitates were collected by filtration and washed with water (100 ml). The collected precipitates were dried at 40 C for 2 hours under high vacuum to obtain 18.5 g of a mixture of 2-[2-(2H- l,2,3-triazol-2-yl)ethoxy]- lH-isoindole- l,3(2H)-dione and 2-[2- (lH- l,2,3-triazol- l-yl)ethoxy]- lH-isoindole- l,3(2H)-dione as a white compound in 65% yield. Analysis: Mass: 259.2 (M+l); for Molecular weight: 258 and Molecular formula: C12H10N4O3; To a solution of mixture of 2-(2-(2H-l,2,3-triazol-2- yl)ethoxy)isoindoline-l,3-dione and 2-(2-(lH-l,2,3-triazol-l-yl)ethoxy)isoindoline-l,3-dione (13 g, 50.3 mmol, obtained from Step 1) in dichloromethane (130 ml) was added hydrazine hydrate (3.7 ml, 75.7 mmol) under stirring at room temperature. After 2 hours, the progress of reaction was monitored by thin layer chromatography using mixture of chloroform and methanol as solvent system. After completion of the reaction the unwanted solid was filtered out and washed with dichloromethane (25 ml). The collective filtrates were concentrated at 40 C under high vacuum to dryness to provide 6.5 g of a mixture of 2-[2-(aminooxy)ethyl]-2H-l,2,3-triazole and l-[2- (aminooxy)ethyl]-lH-l,2,3-triazole, which was used as such in the next step without any further purification; To a solution of sodium salt of (25,5 ?)-6-(benzyloxy)-7-oxo-l,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid (15 g, 54.3 mmol, prepared as per the procedure disclosed in International Patent Application No. PCT/IB2013/059264) in dimethylformamide (75 ml) was added EDC.HC1 (15.6 g, 81.6 mmol) at ambient temperature under stirring. Then N-methyl morpholine (16.5 ml, 0.150 moles) was added followed by HOBT (7.73 g, 50.7 mmol) and reaction mixture was stirred for 5 minutes at ambient temperature. To this reaction mixture was added a solution of mixture of 2-[2-(aminooxy)ethyl]- 2H-l,2,3-triazole and l-[2-(aminooxy)ethyl]-lH-l,2,3-triazole (6.5 g, product from Step 2) in dimethylformamide (6.5 ml) under stirring at 15 C and then allowed to attain room temperature. The progress of reaction was monitored by thin layer chromatography using mixture of chloroform and methanol (9: 1) as solvent system. After completion of the reaction (17 hours), the resulted reaction mixture was slowly poured into chilled water (500 ml) and extracted with ethyl acetate (2×150 ml). The combined organic layer was washed with brine (75 ml) and organic layer was dried over anhydrous sodium sulfate, concentrated on rotavapour to provide 17.5 g of crude compound. It was purified by column chromatography (silica gel 60-120 mesh) using mixture of hexane and acetone as an eluent. The upper spot containing fractions were collected at 30-40% concentration of acetone in hexane and concentrated to dryness under vacuum to provide7.5 g of (25,5 ?)-6-(benzyloxy)-7-oxo-N-[2-(2H-l,2,3-triazol-2-yl)ethoxy]-l,6-diazabicyclo [3.2.1]octane-2- carboxamide. Similarly lower spot containing fractions collected at 40-50% concentration of acetone in hexane were concentrated to dryness under vacuum to provide 5.2 g of of (25,5 ?)-6- (benzyloxy)-7-oxo-N-[2-(lH-l,2,3-triazol-l-yl)ethoxy]-l,6-diazabicyclo[3.2.1]octane-2- carboxamide. In total, 12.7 g was obtained in 70% yield. Analysis: Mass: 385.3 (M-l); for Molecular weight: 386 and Molecular formula: C18H22N6O4.

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

Sources of common compounds: 5181-35-1

To a solution of 2-(2-bromoethoxy)isoindoline- l,3-dione (20 g, 7 mmol, step 1 product) in dimethylformamide (100 ml) was added 1H- 1,2,4 triazole (5.2 g, 7.52 mmol) and cesium carbonate (26.5 g, 8.13 mmol) under stirring at 25-30 C. After 16 hours of stirring, the reaction mixture was filtered through filter paper and the filtrate was slowly poured into chilled water (700 ml) under stirring. After 30 minutes, the separated precipitates were filtered and washed with water (50 ml). The filtered precipitates were dried at 40C for 2 hour under high vacuum to provide 10.5 g of 2-[2- (lH- l,2,4-triazol- l-yl)ethoxy]- lH-isoindole- l,3(2H)-dione as white solid in 55% yield. Analysis: Mass: 259.2 (M+l) for Molecular weight: 258 and for Molecular formula: C12H10N4O3

According to the analysis of related databases, 5181-35-1, the application of this compound in the production field has become more and more popular.

A new synthetic route of 5181-35-1

Some common heterocyclic compound, 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, molecular formula is C10H8BrNO3, 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 5181-35-1

To a solution of 2-(2- bromoethoxy)isoindoline- l,3-dione (5 g, 1.85 mmol, product from step 1 of preparation 10) and lH-tetrazole (1.3 g, 1.85 mmol) in dimethylformamide (25 ml) was added cesium carbonate (6.0 g, 1.85 mmol) in a lot wise under stirring at room temperature. The progress of reaction was monitored by performing thin layer chromatography using mixture of acetone and hexane (3.5:6.5) as solvent. After 16 hours the completion of the reaction was confirmed by thin layer chromatography. The reaction mixture was slowly poured into chilled water (200 ml) under stirring. After stirring for 30 minutes, the precipitates formed were filtered and washed with water (50 ml). The solid compound was dried at 40 C for 2 hours under high vacuum to provide 3.2 g of a mixture of 2-[2-(lH-tetrazol- l-yl)ethoxy]- lH-isoindole- l,3(2H)-dione and 2-[2-(2H-tetrazol-2- yl)ethoxy]- lH-isoindole- l,3(2H)-dione in 66% yield. Analysis: Mass: 260 (M+l) for Molecular weight: 259 and for Molecular formula: C11H9N5O3; To a flask containing mixture of 2-[2-(lH-tetrazol- l-yl)ethoxy]- lH-isoindole- l,3(2H)- dione and 2-[2-(2H-tetrazol-2-yl)ethoxy]- lH-isoindole- l,3(2H)-dione (3.0 g, 1.15 mmol, product from step 1) in dichloromethane (30 ml) was added hydrazine hydrate (0.870 ml, 1.73 mmol) at 25-30 C under stirring and continued stirring for 2 hours. The progress of reaction was monitored by thin layer chromatography. After complete conversion, the unwanted solid was filtered out and washed with dichloromethane (12 ml). The filtrate was concentrated at 40 C under high vacuum to obtain 1.5 g of crude mixture of l-[2-(aminooxy)ethyl]- lH-tetrazole and 2-[2-(aminooxy)ethyl]- 2H-tetrazole (about 100 % yield) and used without further purification in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5181-35-1, its application will become more common.

Application of C10H8BrNO3

Related Products of 5181-35-1, 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. 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

Compound VII: Weigh 2.3g o-nitrobenzyl mercaptan (14.2mmol) And 5.73g of N-(2-bromoethoxy)phthalimide (21.3mmOl) in a round bottom flask, Dissolved with 25ml dimethyl sulfoxide, To the reaction solution was added 3ml of triethylamine (21.3mmol), and reacted at room temperature for 4h; TLC monitoring showed that o-nitrobenzyl mercaptan was completely consumed. To the reaction mixture, an appropriate amount of water was added and the mixture was extracted with dichloromethane for 2-3 times. The organic phase was collected, dried over anhydrous sodium sulfate, Separation by column chromatography (RhoEpsilon:EpsilonAlpha = 5:1), 3.74 g of compound VII (N- (2 – ((2-nitrobenzyl) mercapto) ethoxy) phthalimide was obtained as a white solid (73.2% yield). As shown in FIG. 4, FIG. 4 is a nuclear magnetic hydrogen spectrum of the compound YPi11 prepared in this example.

Reference:
Patent; University of Science and Technology of China; Huang Jianfeng; Shi Jing; Chu Guochao; (21 pag.)CN107698474; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

The important role of 5181-35-1

Synthetic Route of 5181-35-1, 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. 5181-35-1 name is 2-(2-Bromoethoxy)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.

To a solution of 2-(2-bromoethoxy) isoindoline-l,3-dione (10 g, 37 mmol) and tert-buty 2-(lH-tetrazol-5-yl)ethylcarbamate (7.88 g, 37 mmol) in dimethyl formamide (50 ml) was added cesium carbonate ((14.48 g, 44 mmole) in portion wise at 25-30 C under stirring. The reaction mixture was stirred for further 16 hours and filtered; the filtrate was slowly poured into chilled water (400 ml) under stirring and continued stirring for 30 minutes. The formed precipitates of compound were filtered and washed with water (40 ml). The solid compound was dried at 40C for 2 hour under high vacuum, yielded 12 g. The compound was column purified using hexane and acetone as an eluent. The mixture was isolated at 10-15% concentration of acetone in hexane to yield 10 g of 2-{2-[5-(2-tertiary butoxy carbonyl aminoethyl)-2H-tetrazol-2-yl]ethoxy}-lH-isoindole-l,3(2H)-dione and 2-{2-[5-(2-tertiary butoxy carbonyl aminoethyl)-lH-tetrazol-l-yl]ethoxy}-lH-isoindole-l,3(2H)-dione in 67% yield Analysis: Mass: 403 (M+l); for Molecular weight: 402 and Molecular formula: C18H22N6O5..; Hydrazine hydrate monohydrate (1.86 ml, 037.3 mmol) was added to a solution of 2-{2-[5-(2- tertiary-butoxy-carbonyl-aminoethyl)-2H-tetrazol-2-yl]ethoxy}-lH-isoindole-l,3(2H)-dione and 2- {2-[5-(2-tertiary-butoxy-carbonyl-aminoethyl)-lH-tetrazol-l-yl]ethoxy}-lH-isoindole-l,3(2H)- dione (10 g, 24.8 mmol, obtained from step 1) in dichloromethane (10 ml) under stirring at room temperature. After completion of 2 hours of stirring at same temperature the TLC confirms the completion of reaction. The reaction mass was filtered and the solid was washed with dichloromethane (50 ml). The collected filtrate was concentrated at 40C under vacuum to yield 6.75 g of the product, which was used further without any purification. Analysis: Mass: 273 (M+l); for Molecular weight: 272 and Molecular formula: CioH2oN603.

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

Sources of common compounds: 5181-35-1

Reference of 5181-35-1, A common heterocyclic compound, 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, molecular formula is C10H8BrNO3, 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 1A (125 mg, 0.34 mmol), K2CO3 (140 mg, 1.02 mmol)and 1B (1.09 g, 2.04 mmol) in dry DMF (2 mL) was stirred at 70 C for 6 h. After cooling to room temperature, the solution was diluted with MeOH (30 mL). The resulting precipitate was collected by centrifugation (5000 rpm, 15 min). The solid thus obtained was dispersed in water, collected by filtration, washed with MeOH and dried in vacuo. These procedures resulted in 185 mg (73.5 %) of 1C as a yellow solid. MALDI-TOF MS (dithranol): m/z calcd for [M+Na+]: 765.72; found: 765.89. Elemental analysis: calcd for C44H30N4O8 (1C): C, 71.15; H, 4.07; N, 7.54. Found: C,71.10; H, 4.19; N, 7.79.

The synthetic route of 5181-35-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yoshihara, Daisuke; Noguchi, Takao; Tsuchiya, Youichi; Roy, Bappaditya; Yamamoto, Tatsuhiro; Shinkai, Seiji; Chemistry Letters; vol. 44; 6; (2015); p. 812 – 814;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem