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Application 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 mixture of 2-(2-bromoetho xy)isoindo line- 1,3- dione (20 g, 74 mmol, prepared according to the procedure described in step 1 of preparation 10) and 2H-tetrazole-5-carboxylic acid ethyl ester (10.51 g, 74 mmol) in dimethylformamide (100 ml) was added cesium carbonate (24.13 g, 74 mmol) lot wise under stirring at room temperature. After 16 hours, the reaction mixture was filtered through filter paper and filtrate was slowly poured into chilled water (700 ml) under stirring. After 30 minutes of stirring, the product was extracted with ethyl acetate (200 ml and 100 ml). The combined organic layers were washed with brine (100 ml). The organic extract was dried over anhydrous sodium sulfate and concentrated in vacuo to yield 12.5 g of the titled compound. The compound was purified by column chromatography using mixture of acetone and hexane as an eluent. The fractions containing the compound were collected and concentrated to provide 10 g of mixture of ethyl l-{2-[(l,3-dioxo- l,3-dihydro-2H-isoindol-2- yl)oxy]ethyl}- lH-tetrazole-5-carboxylate and ethyl 2-{2-[(l,3-dioxo- l,3-dihydro-2H-isoindol-2- yl)oxy]ethyl}-2H-tetrazole-5-carboxylate in 53% yield Analysis: Mass: 332(M+1); for Molecular weight: 331 and for Molecular formula: C14H13N5O5 ; To a solution of ethyl l-{2-[(l,3-dioxo- l,3-dihydro-2H-isoindol-2-yl)oxy]ethyl}- lH-tetrazole-5-carboxylate and ethyl 2-{2-[(l,3-dioxo- l,3-dihydro-2H-isoindol-2-yl)oxy]ethyl}-2H-tetrazole-5-carboxylate (10 g, 3.02 mmol, product from step 1) in dichloromethane (100 ml) was added hydrazine hydrate (2.26 ml, 4.53 mmol) at 25- 30 C under stirring. The stirring was continued for 2 hours and the progress of reaction was monitored by thin layer chromatography using mixture of chloroform and methanol (9: 1) as solvent. After complete conversion of starting material, the unwanted solid was filtered out and washed with dichloromethane (20 ml). The filtrate was concentrated at 40 C under high vacuum to obtain 6.0 g of mixture of ethyl l-[2-(aminooxy)ethyl]- lH-tetrazole-5-carboxylate and ethyl 2- [2-(aminooxy)ethyl]-2H-tetrazole-5-carboxylate (about 100% yield), the resulted compound was used in the next step without further purification.

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.

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

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Synthetic Route of 5181-35-1, 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 5181-35-1 as follows.

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.

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.

The important role of C10H8BrNO3

Reference of 5181-35-1, 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 5181-35-1 as follows.

To a solution of 2-(2-bromoethoxy)isoindoline- l,3-dione (20 g, 7.4 mmol prepared according to the procedure described in step 1 of preparation 10) and 5-methyl- lH-tetrazole (6.22 g, 7.4 mmol) in dimethylformamide (100 ml) was added cesium carbonate (24.13 g, 7.4 mmol) in a lot wise under stirring at 25-30 C. After 16 hours, completion of the reaction was confirmed by performing the thin layer chromatography using mixture of chloroform and methanol as solvent. The resulted reaction mixture was filtered and the filtrate was slowly poured into chilled water (700 ml) under stirring. After 30 minutes of stirring, the reaction mixture was extracted with ethyl acetate (200 ml and 100 ml). The combined organic layer was washed with brine (100 ml). The organic layer was dried on sodium sulfate and concentrated on rota vapour to provide 18 g of the crude product. The two regio isomers were separated by using column chromatography using mixture of acetone and hexane as an eluent. The upper spot isolated at 15-25% concentration of acetone in hexane yielded 7.0 g of non-polar isomer 2-[2-(5-methyl-2H-tetrazol-2-yl)ethoxy]-lH-isoindole-l,3(2H)-dione. The lower spot isolated at 25-40% concentration of acetone in hexane yielded 3.8 g of polar isomer 2-[2-(5-methyl-lH-tetrazol-l-yl)ethoxy]-lH-isoindole-l,3(2H)-dione. (10.8 g, 53 % yield). Analysis: Mass: 274.2 (M+l); for Molecular weight: 273 and Molecular formula: C12H11N5O3.

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.

New downstream synthetic route of 5181-35-1

Electric Literature of 5181-35-1, 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 5181-35-1 as follows.

To a solution of 2-(2- bromoethoxy)isoindoline-l,3-dione (20 g, 74 mmol) in dimethylformamide (100 ml) added 5-(2- tertiary-butyl-dimethyl-silanyloxy ethyl)- lH-tetrazole (14.81 g, 74 mmol) at 25-30 C under stirring followed by cesium carbonate ((29 g, 88 mmol) in portion wise under stirring. The reaction was continued further at same temperature for 16 hrs and filtered. The filtrate was slowly poured onto chilled water (700 ml) under stirring and continued stirring for 30 minutes. The formed precipitates were filtered and washed with water (70 ml). The solid compound was dried at 40 C for 2 hour under high vacuum to yield crude compound 17.2 g. The crude compound was column purified (silica gel 60-120 mesh size) using hexane and acetone as an eluent. The non-polar spot isolated at 8-12% concentration of acetone in hexane, yielded 8 g of 2-{2-[5-(2-tertiary-butyl- dimethyl-silanyloxy ethyl)-2H-tetrazol-2-yl]ethoxy}-lH-isoindole-l,3(2H)-dione. The polar spot was isolated at 16-20% concentration of acetone in hexane and yielded 4.2 g of 2-{2-[5-(2-tertiary- butyl-dimethyl-silanyloxy ethyl)-lH-tetrazol-l-yl]ethoxy}-lH-isoindole-l,3(2H)-dione as white solid. Analysis: Mass: 418.3 (M+H); for Molecular weight: 417 and Molecular formula: Ci9H27N504Si. 1HNMR (CDCI3): delta.83-7.74 (m, 4H), 5.00 (t, 2H, J=6 Hz), 4.73 (t, 2H, J=6 Hz), 3.98 (t, 2H, J=6.8 Hz), 3.08 (t, 2H, J=7.2 Hz), 0.837 (s, 9H), 0.002 (s, 6H).

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.

Analyzing the synthesis route of 2-(2-Bromoethoxy)isoindoline-1,3-dione

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.

New learning discoveries about 2-(2-Bromoethoxy)isoindoline-1,3-dione

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. 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 5181-35-1

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

Some scientific research about 2-(2-Bromoethoxy)isoindoline-1,3-dione

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.

Synthetic Route 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 mixture of 2-(2-bromoethoxy)isoindoline-l,3-dione (20 g, 74 mmol) and ethyl lH-tetrazol-5-ylacetate (11.55 g, 74 mmol) in DMF (100 ml) was added cesium carbonate (29 gm, 0.088 mol) in portion wise at 25-30 C under stirring. The stirring was continued for 16 hrs. The reaction mixture was filtered and the collected filtrate was slowly poured onto chilled water (700 ml) under stirring. The formed precipitates of compound were filtered on Buchner funnel and washed with water (70 ml). The solid compound was dried at 40C for 2 hour under reduced pressure to yield crude compound 18.0 g. The crude compound was column purified using hexane and acetone. The non-polar spot isolated at 10-15% concentration of acetone in hexane and yielded 8.0 g of ethyl (2-{2-[(l,3-dioxo-l,3-dihydro-2H-isoindol-2-yl)oxy]ethyl}-2H- tetrazol-5-yl)acetate. The polar spot isolated at 20-25% concentration of acetone in hexane, and the pure fractions were collected and concentrated on rota evaporator which yielded 5.0 g of ethyl (1- {2-[(l,3-dioxo-l,3-dihydro-2H-isoindol-2-yl)oxy]ethyl}-lH-tetrazol-5-yl)acetate as white solid in 53% yield. Analysis: Mass: 346.3 (M+H); for Molecular weight: 345 and Molecular formula: C15H15N5O5. 1HNMR (CDCI3): delta 7.84-7.26 (m, 4H), 5.05 (t, 2H, J=5.2 Hz), 4.77 (t, 2H, J=5.6 Hz), 4.23-4.18 (q, 2H), 3.97 (s, 2H), 1.27 (t, 3H, J= 7.2 Hz).

The important role of 2-(2-Bromoethoxy)isoindoline-1,3-dione

Statistics shows that 2-(2-Bromoethoxy)isoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 5181-35-1.

Electric Literature of 5181-35-1, These common heterocyclic compound, 5181-35-1, name is 2-(2-Bromoethoxy)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.

2-(2-Bromoethoxy)isoindoline-1 ,3-dione (Intermediate Q) (1.00 g, 3.70 mmol) was combined with cone HBr (48 wt% in water, 4.5 mL) and acetic acid (3 mL, 52.4 mmol). The mixture was heated at 120 C for 15 min. The reaction mixture was cooled, the precipitate was removed by filtration and the filtrate concentrated under reduced pressure to afford the subtitle compound 0-(2-Bromoethyl)hydroxylamine, HBr as a tan solid (550 mg, 74%); 1 H NMR delta: 3.72 (2H, m), 4.28 (2H, m), 10.70 (3H, br s).

Statistics shows that 2-(2-Bromoethoxy)isoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 5181-35-1.

Reference:
Patent; RESPIVERT LIMITED; WALTERS, Iain; BIRCH, Louise; HILL-COUSINS, Joseph; COLLINGWOOD, Stephen, Paul; STEVENSON, Christopher, Scott; (126 pag.)WO2017/109513; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

The important role of 5181-35-1

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

These common heterocyclic compound, 5181-35-1, name is 2-(2-Bromoethoxy)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. category: indolines-derivatives

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; To a solution of (2S,5R)-6-(benzyloxy)-7-oxo-l,6- diaza-bicyclo[3.2.1]octane-2-carboxylic acid (6.2 g, 22 mmol) in dimethylformamide (50 ml) was added EDC.HC1 (6.45 g, 33.6 mmol) at ambient temperature under stirring. To this was added N- methyl morpholine (7.23 ml, 67.3 mmol) followed by HOBT (3.04 g, 22 mmol) under stirring and reaction mixture was stirred for 5 minutes and cooled to 15C and a solution of mixture of tert- butyl (2-{ l-[2-(aminooxy)ethyl]-lH-tetrazol-5-yl}ethyl)carbamate and tert-buty (2-{2-[2- (aminooxy)ethyl]-2H-tetrazol-5-yl}ethyl)carbamate (6.72 g, 24.7 mmol) in dimethylformamide (12 ml) was slowly added and allowed to reach ambient temperature and stirred for 16 hours. The progress of reaction was monitored by TLC, after complete conversion of starting material the reaction mixture was slowly poured onto 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. The organic layer was concentrated on rotavapour to provide 4.2 g of crude compound. The crude compound was column purified by using hexane and acetone as an eluent. The non-polar spot isolated at 10-15% concentration of acetone in hexane yielded 1.6 g of (2S,5R)-N-{2-[5-(2-tertiary butoxy carbonyl aminoethyl)-2H-tetrazol-2-yl]ethoxy}-6- benzyloxy-7-oxo-l,6-diazabicyclo[3.2.1]octane-2-carboxamide. The polar spot isolated at 20-25% concentration of acetone in hexane and the pure fractions were collected and concentrated on Rota evaporator to yield 1.4 g of (2S,5R)-N-{2-[5-(2-tertiary butoxy carbonylaminoethyl)-lH-tetrazol-l- yl]ethoxy}-6-benzyloxy-7-oxo-l,6-diazabicyclo[3.2.1] octane-2-carboxamide as white compound, in 25% yield. Analysis: Mass: 531 (M+l); for Molecular weight: 530 and Molecular formula: C24H34N8O6. 1H NMR (DMSO-de): delta 9.30 (s, 1H), 7.43-7.33 (m, 5H), 5.05-5.02 (m, 1H), 4.90-4.83 (m, 3H), 4.47-4.43 (m, 2H), 3.92-3.91 (d, 1H, J= 7.2 Hz), 3.59-3.57 (m, 2H), 3.30 (s, 1H), 3.11-3.08 (m, 2H), 2.99-2.97(m, 1H), 2.71-2.68 (m, 1H), 2.29-2.24 (m, 2H),m 2.04-1.89 (m, 3H), 1.49 (s, 9H).

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