Month: March 2021

Application of 654-70-6,Some common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, molecular formula is C8H5F3N2, 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 reaction container was charged with 70 g of commercially available 4-cyano-3-trifluoromethylaniline (LC surface percentage: 99.39%) and 350 mL of ethanol, and the temperature was increased to 72C. After the mixture was stirred at 72 to 75C for 30 minutes, insoluble matters were removed by filtration at the same temperature and the mixture was further washed with 10 mL of ethanol. The filtrate thus obtained was cooled to 57C, and 360 mL of water was dropped at the same temperature over about 4 hours. 30 mg of 4-cyano-3-trifluoromethylaniline that had been previously purified was seeded thereto and the resultant mixture was cooled to 45C, and thereafter stirred at the same temperature for 30 minutes. Then, the mixture was cooled to 25C and stirred at the same temperature for 1 hour. Crystals were separated by filtration and washed with a mixed solvent of 56 mL of ethanol and 56 mL of water to give 83.81 g of wet crystals. The wet crystals were dried under reduced pressure to obtain 50.61 g of 4-cyano-3-trifluoromethylaniline. The LC surface percentage was 99.90%, and the yield was 72.3%. A reaction container was charged with 68 mL of N,N-dimethylacetamide, 22.1 g of methacrylic acid, and 38 mg of dibutylhydroxytoluene, and the temperature was reduced to -5C. Thionyl chloride in an amount of 30.6 g was dropped thereto at -3.8 to 0.3C over 50 minutes, and the mixture was kept at -4.0 to -0.8C for 30 minutes. A solution obtained by dissolving 36.0 g of 4-cyano-3-trifluoromethylaniline obtained as described above in 79 mL of N,N-dimethylacetamide was dropped into the reaction container at -5.3 to 0C over 65 minutes. The container for dropping was washed with 11 mL of N,N-dimethylacetamide, the washing liquid was added to the reaction solution, and the solution was kept at -5.3 to 0C for 1 hour. After completion of the reaction, the obtained reaction solution was dropped to a mixed solution of 306 mL of ethyl acetate and 252 mL of water at 20C or less. The solution was washed with 18 mL of N,N-dimethylacetamide and the washing solution and the mixed solution were combined, and 378.1 g of an aqueous 16% sodium carbonate solution was added to the solution to adjust the pH to 7.1. The resultant solution was stirred for 30 minutes and made to stand still for 30 minutes, followed by liquid separation. The liquid separation speed calculated in the same manner as in Example 1 was 1.7 m/hr. The organic layer was added with 571.8 g of 15% saline water to set the internal temperature to 60C. The resultant solution was stirred for 30 minutes and made to stand still for 30 minutes, followed by liquid separation. The liquid separation speed calculated in the same manner as in Example 1 was 3. 9 m/hr. The organic layer was added with 571.8 g of 15% saline water to set the internal temperature to 60C. The resultant solution was stirred for 30 minutes and made to stand still for 30 minutes, followed by liquid separation. The liquid separation speed calculated in the same manner as in Example 1 was 3. 6 m/hr. The organic layer was further added with 571. 8 g of 15% saline water to set the internal temperature to 60C. The resultant solution was stirred for 30 minutes and then made to stand still for 30 minutes, followed by liquid separation. The liquid separation speed calculated in the same manner as in Example 1 was 3. 0 m/hr. Then, the organic layer was charged with 180 mL of chlorobenzene, and ethyl acetate and chlorobenzene were distilled out in an amount of 222.3 g by vacuum concentration. Next, 504 mL of chlorobenzene, 1.8 g of activated carbon and 4.9 g of gamma-alumina were charged and the mixture was stirred at 75C for 30 minutes. The alumina and activated carbon were separated by filtration at the same temperature and washed with 36 mL of chlorobenzene. The filtrate and the washing solution were combined, and 545.5 g of chlorobenzene was distilled out by vacuum concentration, and then the mixture was cooled to 20C and stirred at 15 to 20C for 2 hours. Crystal were separated by filtration and washed with 108 mL of a chlorobenzene solution dissolved with 0.45 g of dibutylhydroxytoluene to give 48.94 g of wet crystals. After drying the crystal under reduced pressure, 45.27 g of crystals of N-methacryloyl-4-cyano-3-trifluoromethylaniline was obtained. The LC surface percentage was 99.92%, and the yield was 92.1%.

The synthetic route of 654-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2204362; (2010); A1;,
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Synthetic Route of 57381-37-0, 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. 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under the protection of nitrogen,To 2-(3-((6-fluoroquinolin-4-yl)oxy)-8-azabicyclo[3.2.1]oct-8-yl)propanamide (100 mg, 0.3 mmol),2-bromo-5-chlorobenzonitrile (63 mg, 0.3 mmol) and NaOH (14 mg, 0.3 mmol) in 2 mL of NMPCuI (6 mg, 0.03 mmol) was added to the solution.The reaction mixture was stirred at 120 C overnight.The reaction system was poured into 10 mL of water.Extract with EA (10 mL x 3).The organic phase is washed with saturated brine.Dry anhydrous Na2SO4 and concentrate under reduced pressure.The residue was chromatographed on silica gel (DCM:MeOH = 10:1)Purification afforded 30 mg (yield: 21%) of the title compound.It is a white solid.

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, 2-Bromo-5-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chengdu Hai Borui Pharmaceutical Co., Ltd.; Chengdu Beite Pharmaceutical Co., Ltd.; Huang Haoxi; Liu Guanfeng; Ren Junfeng; Yi Shoubing; Chen Tonghun; He Quanhong; Wu Xiancai; Li Yingfu; Su Zhonghai; (91 pag.)CN109575022; (2019); A;,
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Related Products of 96606-37-0, 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 96606-37-0 as follows.

Example 7: Synthesis OF 3-AMINO-4-ETHOXY-6- (4-HYDROXY-PIPERIDIN-1-YL)- benzo [B] THIOPHENE-2-CARBOXYLIC acid amide To a solution of 1.0 g (6.4 mmol) of 2, 4,6-trifluorobenzonitrile in MEOH (35 mL) was added 0.65 g (6.4 mmol) of 4-hydroxypiperidine and 1.2 mL (6.7 mmol) OFF, N diiisopropylethylamine. The mixture was heated to 65 C FOR 4 h then cooled to room temperature and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography to provide 0.325 g (21 %) OF 2, 6-DIFLUORO-4- (4-HYDROXY- PIPERIDIN-L-YL)-BENZONITRILE as a white solid.

According to the analysis of related databases, 96606-37-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2005/12283; (2005); A1;,
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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. 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 2-(3-Nitrophenyl)acetonitrile

To a suspension of sodium hydride (617 mg, 14.16 mmol) in dimethylformamide (16 mL) under 10C, a solution of 3-nitrophenylacetonitrile (1.15 g, 7.09 mmol) and 2-(2-bromoethoxy)tetrahydro-2H-pyran (3.24 g, 15.5 mmol) in dimethylformamide (5 mL) was added, and the mixture was stirred for 3 hours at room temperature. The reaction mixture was poured into saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtrated, and then the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography. To the resulting oil was added methanol (15 mL) followed by p-toluenesulfonic acid mono-hydrate (90.7 mg), and then the mixture was stirred for three and half hours at room temperature. Water was added to the reaction mixture, the mixture was concentrated in vacuo. Then, saturated aqueous ammonium chloride was added thereto, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtrated, and then the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography to give 740 mg of the title compound as a yellow solid. High-performance liquid chromatography/mass spectrometry m/z 251 (M+H) Retention time: 2.09 min.

The synthetic route of 621-50-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1679069; (2006); A1;,
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Reference of 21803-75-8, 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 21803-75-8 as follows.

To a solution of phosgene (2.3 mL, 20% in toluene) in dry DCM (20 mL) was added a solution of 2-chloro-4-cyanoaniline (367 mg) and DIEA (372 mg) in dry DCM slowly. The resulting mixture was stirred at room temperature for 1 hr prior to evaporation to dryness. The residue was dissolved in DCM (10 mL) to which a solution of compound 1f (Example 1,510 mg) and DIEA (310 mg) in DCM was added. The resulting mixture was stirred overnight at room temperature. Aqueous sodium bicarbonate was added and the mixture was extracted with DCM. The organic phase was dried over MgS04 and evaporated to dryness.

According to the analysis of related databases, 21803-75-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SB PHARMCO PUERTO RICO INC; NEUROCRINE BIOSCIENCES INC; WO2005/63749; (2005); A1;,
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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. 4210-32-6, name is 4-(tert-Butyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C11H13N

Step 2: Preparation of 3-(4-(tert-butyl)-phenyl)-6-methoxyisoquinolin-1(2H)-one To a stirred solution of N,N-diethyl-4-methoxy-2-methylbenzamide (1 g, 4.52 mmol) in THF (10 ml) was added n-BuLi (2.82 ml, 4.52 mmol, in hexane) at -78¡ã C. and stirred for 1 h. Then to this 4-(tert-butyl)benzonitrile (0.72 g, 4.52 mmol) was added at same temperature and allowed to warm to room temperature and continued the stirring for another 1 h at room temperature. The reaction mixture was quenched with saturated NH4Cl solution and extracted with EtOac (2*100 ml). The organic phase was washed with brine, dried on Na2SO4, and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (20percent ethyl acetate in pet ether) to get desired compound (0.72 g, 46.7percent) as a solid. 1H NMR (400 MHz, DMSO-d6): delta ppm 11.26(s, 1H), 8.11-8.09 (d, J=8 Hz, 1H), 7.73-7.71 (d, J=8 Hz, 2H), 7.52-7.50 (d, J=8 Hz, 2H), 7.06 (s, 1H), 7.05-7.03 (d, J=8 Hz, 1H), 6.82 (s, 1H), 3.89 (s, 3H), 1.32 (s, 9H); MS: MS m/z 308.2 (M++1).

According to the analysis of related databases, 4210-32-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael; US2013/115190; (2013); A1;,
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Some common heterocyclic compound, 939-80-0, name is 4-Chloro-3-nitrobenzonitrile, molecular formula is C7H3ClN2O2, 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. HPLC of Formula: C7H3ClN2O2

1) Production of 4-isobutoxy-3-nitrobenzonitrile 19.5 g of 4-chloro-3-nitrobenzonitrile was dissolved in 200 ml of DMF, and after 16.0 g of 2-methyl-1-propanol, 30 g of potassium carbonate and 7.1g of potassium iodide were added thereto, the mixture was heated and stirred at 80C for 24 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated saline solution and dried over magnesium sulfate. After the magnesium sulfate was filtered off, solvent was evaporated under reduced pressure and the residue was subjected to silica gel column chromatography. Hexane-ethyl acetate (10:1) was used as an eluent and 5.9 g of the object compound was obtained as a pale yellow crystal.1H-NMR(CDCl3)deltappm: 1.07(6H, d, J=6.76Hz), 2.11?2.25(1H, m), 3.94(2H, d, J=6.43Hz), 7.15 (1H, d, J=8.91Hz), 7.81(1H, dd, J=8.91, 2.15Hz), 8.14(1H, d, J=2.15Hz)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 939-80-0, its application will become more common.

Reference:
Patent; Fuji Yakuhin Co., Ltd.; EP1471065; (2004); A1;,
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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. 2469-99-0, name is 3-Oxobutanenitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 2469-99-0

General procedure: 3-Acetyl-2-aminothiophene Derivatives; General Procedure Carbonyl compound (0.025 mol) was added to freshly prepared cya-noacetone (0.03 mol) in either MeOH or EtOH (40 mL). Sublimed sul-fur S8 (0.03 mol) and piperidine (0.03 mol) were added and the mix-ture was stirred and heated to 55-65 C for 24 h. Ice was then addedand the formed precipitate was filtered under vacuum and washedwith water. The obtained solid was crystallised from a suitable sol-vent, with the exception of 4g and 4j, which were collected directlywithout further purification.

According to the analysis of related databases, 2469-99-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Abdelwahab, Ahmed B.; Hanna, Atef G.; Kirsch, Gilbert; Synthesis; vol. 48; 17; (2016); p. 2881 – 2888;,
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Electric Literature of 134604-07-2, A common heterocyclic compound, 134604-07-2, name is 1-Cyano-2-bromo-5-nitrobenzene, molecular formula is C7H3BrN2O2, 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.

Description for D422-(2-methylpropyl)-5-nitrobenzonitrile (D42)To a solution of isobutylboronic acid (5.89 g), 2-bromo-5-nitrobenzo nitrile (12.5 g) and Cs2C03 (35.9 g) in toluene (150 mL) and water (5 mL) stirred under nitrogen at room temperature was added solid PdCI2(dppf CH2CI2 adduct (2.248 g) in one charge. The reaction mixture was stirred at 100 C for 16 h. After cooling the reacion, the solvent was removed in vacuo. The residue was purified by column chromatography to give 2-(2-methylpropyl)-5-nitrobenzonitrile (D42) (11 g) as a light yellow oil. deltaEta (CDCI3, 400MHz): 1.00 (6H, d), 2.06 (1 H, m), 2.86 (2H, d), 7.52 (1 H, d), 8.37 (1H, dd), 8.51 (1H, d).

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; GLAXO GROUP LIMITED; LIN, Xichen; REN, Feng; ZHANG, Haibo; WO2011/113309; (2011); A1;,
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Synthetic Route of 6621-59-6, 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. 6621-59-6, name is 6-Bromohexanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: K2CO3, KOH and TBAB were added to a solution of each triazole compound (7a-c) in ACN. Each solution was stirred for 30 min at room temperature; alkyl bromide was added, and the reaction proceeded for 3-24 h at room temperature. The solid was filtered and then washed with diethyl ether. The solvent of the filtrate was removed in vacuo and purified by silica gel column chromatography (hexane/ethyl acetate) to yield the desired compound or crude mixture, which were reacted in the next step of deprotection.

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

Reference:
Article; Lee, Sun-Mi; Yoon, Kyoung Bin; Lee, Hyo Jeong; Kim, Jiwon; Chung, You Kyoung; Cho, Won-Jea; Mukai, Chisato; Choi, Sun; Kang, Keon Wook; Han, Sun-Young; Ko, Hyojin; Kim, Yong-Chul; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5036 – 5046;,
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