Category: Benzisoxazole

37924-85-9, 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. 3-(Bromomethyl)benzo[d]isoxazole, cas is 37924-85-9,the Benzisoxazole compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To NaOMe (25% soln, 0.5 mL, 2.2 mmol) in MeOH (5 mL) was added thiosemicarbazide 9 (200 mg, 2.2 mmol). Diethyloxalate (0.3 mL, 2.2 mmol) was then added dropwise. The mixture was heated at 65 C for 2 h and then cooled to rt. 1-(Bromomethyl)-4-chlorobenzene (500 mg, 2.4 mmol) was added in one portion; stirring was continued at rt for 3 h and then heated overnight at 50 C. The reaction mixture was concentrated. The residue was dissolved in EtOAc (40 mL), washed with water (20 mL), and brine (20 mL). The organic phase was dried over Na2SO4, concentrated and purified by silica gel column chromatography (EtOAc w/ 0.2% HOAc). The product was triturated in Et2O to afford 59 mg of 6g as a light yellow solid (10% yield)

The chemical industry reduces the impact on the environment during synthesis,37924-85-9,3-(Bromomethyl)benzo[d]isoxazole,I believe this compound will play a more active role in future production and life.

Reference£º
Article; Hin, Niyada; Duvall, Bridget; Berry, James F.; Ferraris, Dana V.; Rais, Rana; Alt, Jesse; Rojas, Camilo; Slusher, Barbara S.; Tsukamoto, Takashi; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2088 – 2091;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

36216-80-5, 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. Benzo[d]isoxazol-3-amine, cas is 36216-80-5,the Benzisoxazole compound, it is a common compound, a new synthetic route is introduced below.

A mixture of intermediate 3 (0.0025 mol) and triethylamine (0.0025 mol) in CHzClz (10 ml) was stirred at RT. 2-methylpropanoyl chloride (0.0025 mol) was added dropwise and the reaction mixture stirred overnight at RT. The reaction mixture was washed 2 times with H20. The organic layer was separated, dried (MgS04), filtered off and the solvent was evaporated dry. The residue was further purified by column chromatography over silicagel (eluent: CH2Cl2) yielding 0.235 g of compound 8 and a fraction which was further purified using reversed phase HPLC chromatography on a Xterra MS C18 column (3. 5, um, 4.6 x 100 mm) with a flow rate of 1.6 m ./min (Elution conditions: three mobile phases (mobile phase A 95% 25mM ammoniumacetate + 5% acetonitrile; mobile phase B: acetonitrile ; mobile phase C: methanol) were employed to run a gradient condition from 100 % A to 50% B and 50% C in 6.5 min. , to 100 % B in 1 min, 100% B for 1 min. and re-equilibrate with 100 % A for 1.5 min.) yielding 0.010 g of compound 7 (Melting Point 130C).

The chemical industry reduces the impact on the environment during synthesis,36216-80-5,Benzo[d]isoxazol-3-amine,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; JANSSEN PHARMACEUTICA N.V.; WO2005/89753; (2005); A2;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

651780-27-7, 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. Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, cas is 651780-27-7,the Benzisoxazole compound, it is a common compound, a new synthetic route is introduced below.

Diethyl malonate (12.6 g, 79 mmol) was added to a suspension of sodium hydride (3.16 g, 132 mmol) in dimethylsulfoxide (60 ml) over 30 min. The temperature of the reaction rose to 60 C and the mixture clarified. 1,4-Dibromo-2-nitrobenzene (10 g, 36.0 mmol) was added and the solution was maintained for 2 h at 100 C. The reaction mixture was allowed to cool to rt and was poured into ice (300g-400g). The precipitated solids were isolated by filtration and dried to provide 11.0 g of the product (89%). The ester (11.0 g, 32.0 mmol) was diluted with a 2 N solution of sodium hydroxide (32 mL, 63 mmol) and the reaction mixture was maintained at room temperature for 16 h. The aqueous layer was extracted with dichloromethane (20 mL) and was acidified. The precipitated solids were isolated by filtration and dried to provide 7.00 g of the acid (89%). Sulfuric acid (1 mL) was added to a solution of the acid (7.00 g, 27.0 mmol) in ethanol (60 ml). The reaction mixture was warmed to reflux, maintained for 2 h, and was concentrated under reduce pressure. The residue was partitioned between ethyl acetate (250 mL) and saturated sodium carbonate (50 mL) and the organic layer was washed with saturated sodium carbonate (50 mL) and brine (50 mL). The organic layer was dried (sodium sulfate) and concentrated to provide 8.00 g (98%) of the ester as a liquid. Under N2 atmosphere, sodium ethylate was formed with sodium (33.5 g, 1.46 mol) in ethanol (1.0 L). Isoamylnitrite (225 mL) was added to a solution of the ester (420 g, 1.46 mol) in ethanol (3 L) in a 10 L three-necked round bottom flask and the mixture was warmed to 60 C. A solution of sodium ethoxide, prepared from sodium metal (33.5 g, 1.46 mmol) in ethanol (1 L) was added dropwise and the reaction mixture was maintained for 2 h. The reaction mixture was allowed to cool to rt and was neutralized with 2 N hydrochloric acid. The reaction mixture was extracted with ethyl acetate (4 x 2L) and the combined organic layers were washed with water (2 x 1 L) and brine (2 x 1 L) and dried (sodium sulfate). The residue was purified by chromatography (1/1 to 0/1 hexane/ethyl acetate) to provide 110 g of the product ( 28%). 10% Palladium on carbon (1.5g) and triethylamine (7.5 g, 82.4 mmol) were added to a solution of ethyl 6-bromobenzisoxazole-3-carboxylate (20g, 0.081mol) in ethanol (300ml) at 0 C under an atmosphere of nitrogen. The nitrogen atmosphere was removed by evacuation and replaced with hydrogen gas, and the reaction mixture was maintained for 1 hour. The hydrogen atmosphere was removed by evacuation and replaced with nitrogen gas, and the palladium removed’by filtration through Celite. The filter cake was washed with ethanol (3 x 50 mL) and the filtrates were concentrated. The residue was- dissolved in dichloromethane (200 mL) and the solution was washed with water (4 x 50 mL), dried (sodium sulfate) and evaporated to provide 13.0 g of the product as a yellow solid (96%). The ester was saponified using sodium hydroxide to provide the acid. The acid was coupled with 1,4-diazabicyclo[3.2.2]nonane according to procedure A.

The chemical industry reduces the impact on the environment during synthesis,651780-27-7,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2005/111038; (2005); A2;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

It is a common heterocyclic compound, the Benzisoxazole compound, Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, cas is 651780-27-7 its synthesis route is as follows.

Toluene (40 mL) was added to a flask containing ethyl [6-BROM-1,] 2-benzisoxazole-3-carboxylate (3.15 g, 11.7 mmol), tetrakis (triphenylphosphine) palladium [(0)] (835 mg, 0.723 mmol, Strem), cesium carbonate (4.12 g, 12.6 mmol, Aldrich), and 2- (trifluoromethyl) phenylboronic acid (2. [38] g, 12.5 mmol, Aldrich) under argon. This mixture was heated in a 100 C oil bath for 35 hours. The mixture was diluted with EtOAc (250 mL) and washed with 4: 1 water: brine (250 [ML)] followed by brine (250 mL). The organics were filtered through a [1″PLUG] of silica gel and evaporated. Product was split in two, adsorbed onto silica gel, and purified on Biotage Flash 40 M+ silica cartridges using 20% EtOAc in heptane. Yield was 2.08 g of orange solid. [‘H] NMR (400 MHz, DMSO-d6) [5] ppm 1.42 (t, [J=7.] 15 Hz, 3 H) 4.51 (q, [J=7.] 05 Hz, 2 H) 7.52 (d, J=7. 46 Hz, [1] H) 7.51 (d, [J=8.] 09 Hz, 1 H) 7.71 (t, J=7. 57 Hz, [1] H) 7.79 (t, [J=7.] 36 Hz, 1 H) 7.91 (d, [J=7.] 67 Hz, [1] [H)] 7.93 (s, 1 H) 8.14 (d, J=8. 09 Hz, 1 H).

651780-27-7, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,651780-27-7 ,Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18428; (2004); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

Name is Benzo[d]isoxazol-3-amine, as a common heterocyclic compound, it belongs to Benzisoxazole compound, and cas is 36216-80-5, its synthesis route is as follows.

EXAMPLE 27 1-(2,6-DICHLOROBENZOYL)-3-(3-BENZISOXAZOLYL)UREA 3-Aminobenzisoxazole (300 grams) and 2,6-dichlorobenzoyl isocyanate (600 grams) in 50 ml. methylene chloride were stirred at room temperature for one hour. The solvent was then evaporated and the precipitate recrystallized from ethanol. The identity of the product was determined by NMR and IR analysis, yield 500 mg., m.p.=212-215 C. Calculated: C, 51.45; H, 2.59; N, 12.00. Found: C, 51.35; H, 2.40; N, 11.84.

36216-80-5, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,36216-80-5 ,Benzo[d]isoxazol-3-amine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; Eli Lilly and Company; US4336264; (1982); A;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

89976-56-7, 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. 5-Methylbenzo[d]isoxazol-3-amine, cas is 89976-56-7,the Benzisoxazole compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-methyl-benzo[d]isoxazol-3-ylamine (4.6 g) in anhydrous DCM (50 mL) was slowly added a solution of (Boc)2O in anhydrous DCM (50 mL) and 50 mg of DMAP. After refluxing overnight, TLC showed complete reaction. LCMS/ELSD showed formation of the desired product (M+H: 349.2). The reaction was quenched with aqueous sodium carbonate (1 M, 50 mL) and stirred for 1 hr at room temperature. The organic layer was dried over anhydrous sodium sulfate. After rotary evaporation of most solvent, the concentrated solution was loaded onto a 50 g ISOLUTE silica cartridge and eluted with EtOAc/Hexane (from 1:10 to 1:2). Rotary evaporation of solvent provided a light yellow solid. Trituration with EtOAc/Hexane (1:9) provided a white solid (4.56 g). 1H-NMR (300 MHz, CDCl3) delta 7.47 (d, 1H), 7.40 (d, 1H), 7.37 (s, 1H), 2.48 (s, 3H), 1.41 (s, 18H). LC/MS (ESI): M+H+ 349.2.

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 5-Methylbenzo[d]isoxazol-3-amine, 89976-56-7

Reference£º
Patent; Player, Mark R.; Lu, Tianbao; Hu, Huaping; Zhu, Xizhen; Teleha, Christopher; Kreutter, Kevin; US2007/225282; (2007); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

As a common heterocyclic compound, it belongs to Benzisoxazole compound, name is Benzo[d]isoxazol-3-amine, and cas is 36216-80-5, its synthesis route is as follows.

A solution of 1 ,2-benzisoxazol-3-amine (1.00 g; CASNo. 36216-80-5) and triethylamine (1.09 mL) in acetonitrile (5 mL) was added dropwise to at 0 0C solution of phenyl chloroformate (0.989 mL) in THF (20 mL). The reaction was stirred at 0 0C for 1 h and then allowed to warm to room temp overnight. The reaction was diluted with ethyl acetate and washed with 1 N HCI and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated to give the crude product as a reddish brown solid. The solid was triturated with refluxing diisopropyl ether, cooled to room temp, and filtered to give the final product as a tan solid (1.22 g, 64%). m/z 255 (MH+).

36216-80-5, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,36216-80-5 ,Benzo[d]isoxazol-3-amine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; PFIZER INC.; WO2009/127948; (2009); A1;; ; Patent; PFIZER INC.; WO2009/127949; (2009); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

As a common heterocyclic compound, it belongs to Benzisoxazole compound, name is 3-(Bromomethyl)benzo[d]isoxazole, and cas is 37924-85-9, its synthesis route is as follows.

(b) Sodium hydride (50% in mineral oil, 3.4 g, 0.071 mole) is washed free of mineral oil with hexane (3*30 mL) and suspended in dimethylformamide (100 mL). This suspension is well stirred and maintained near room temperature (water bath) during the dropwise addition of a solution of imidazole (4.8 g, 0.071 mole) in dimethylformamide (25 mL). The reaction mixture is stirred at room temperature for 1 hour when 3-bromomethyl-1,2-benzisoxazole (15.0 g, 0.071 mole) is added all at once. The mixture is then heated at 85 C. for 8 hours. The solvent is evaporated in vacuo and the residue is taken up in methylene chloride (200 mL) and washed with water (3*50 mL). The organic solution is dried over anhydrous sodium sulfate, filtered and evaporated to give 3-[(1H-imidazol-1-yl)methyl]-1,2-benzisoxazole, which is purified by recrystallisation from isopropanol, m.p. 52-55 C.

37924-85-9, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,37924-85-9 ,3-(Bromomethyl)benzo[d]isoxazole, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; Ciba-Geigy Corporation; US4859691; (1989); A;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

As a common heterocyclic compound, it belongs to Benzisoxazole compound, name is 3,6-Dichlorobenzo[d]isoxazole, and cas is 16263-54-0, its synthesis route is as follows.

To a solution of l-Boc-5-trifluoromethoxybenzimidazole-2-one (5 g, 15.7 mmol) in DMF (20 ml) was added 3,6-dichlorobenzoisoxazole (3.0 g, 15.7 mmol) and Cs2CO3 (11 g, 31.4 mmol). The suspension was heated to 15O0C in an oil bath and stirred overnight. The mixture was then cooled to room temperature, diluted with water (30 ml) and extracted with ethyl acetate (2×20 ml). The organic extracts were combined, dried over anhydrous Mg2SO4, and concentrated to dryness. The residue was purified by silica gel column chromatography using hexane/ethyl acetate (4:1) as solvent system. Fractions containing earlier eluted product were combined and concentrated to obtain l-[3-(6-chloro)-benzisoxazoyl]-5- trifluoromethoxylbenzimidazole-2-one as a white solid. 1H NMR (DMSO, 500 MHz) delta 8.28 (d, J=9.0Hz, IH), 8.12 (s, IH), 7.74 (d, J=9.0Hz, IH), 7.54 (d, J=8.5, IH), 7.14 (d, J=8.5, IH), 7.13 (s, IH). Fractions containing later eluted product were combined and concentrated to obtain l-[3-(6-chloro)-benzisoxazoyl]-6-trifluoromethoxylbenzimidazole-2-one as a white solid. 1H NMR (DMSO, 500 MHz) delta 8.28 (d, J=9.0Hz, IH), 8.12 (s, IH), 7.74 (d, J=9.0Hz, IH), 7.66 (brs, IH), 7.54 (d, J=8.5, IH), 7.13 (brs, IH).

16263-54-0, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,16263-54-0 ,3,6-Dichlorobenzo[d]isoxazole, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; MERCK & CO., INC.; WO2006/22954; (2006); A2;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics

36216-80-5, 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. Benzo[d]isoxazol-3-amine, cas is 36216-80-5,the Benzisoxazole compound, it is a common compound, a new synthetic route is introduced below.

(Synthesis of X-4) In a three-neck flask, after filling the inside of flask with nitrogen gas, 6.5 g of 10% Pd-C (produced by Wako Pure Chemical Industries, Ltd.) was added, and 2,000 mL of ethanol and the entire amount of the crude product of Compound (X-3) obtained above were further added. The resulting mixture was heated/refluxed, and 55 mL (3 molar equivalents) of formic acid was slowly added dropwise thereto, followed by stirring at this temperature for 5 hours. The resulting reaction mixture was cooled to an inner temperature of 25C and then subjected to Celite filtration and to the mother solution separated by filtration, 105 g of 1,5-naphthalenedisulfonic acid was added. After raising the inner temperature to 70C, the mixture was stirred for 30 minutes and then gradually cooled to room temperature, and the crystal was separated by filtration to obtain 100 g of Compound (X-4). The yield was 72% based on Compound (X-1) as the starting material. The obtained crystal was pale brown. 1H NMR (deuterated DMSO): delta6.95-6.98 (1H), delta7.02-7.04 (1H), delta7.40-7.51 (3H), delta7.90-7.95 (1H), delta8.75 (1H), delta8.85-8.88 (2H), delta9.03 (2H), delta10.89 (1H).

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 Benzo[d]isoxazol-3-amine, 36216-80-5

Reference£º
Patent; FUJIFILM Corporation; EP2460799; (2012); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics