Category: 654-70-6

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.

Thionyl chloride (46.02 g, 0.39 mol) was added dropwise to a cooled solution (less than 4 C) of (/?)-3-bromo-2-hydroxy-2-methylpropanoic acid (51.13 g, 0.28 mol) in 300 mL of THF under an argon atmosphere. The resulting mixture was stirred for 3 h under the same condition. To this was added Et3N (39.14 g, 0.39 mol) and stirred for 20 min under the same condition. After 20 min, 5-amino-2- cyanobenzotrifluoride (40.0 g, 0.21 mol), 400 mL of THF were added and then the mixture was allowed to stir overnight at rt. The solvent was removed under reduced pressure to give P-75003-PC a solid which was treated with 300 mL of H20, extracted with EtOAc (2 X 400 mL). The combined organic extracts were washed with saturated NaHCC>3 solution (2 X 300 mL) and brine (300 mL). The organic layer was dried over MgS04 and concentrated under reduced pressure to give a solid which was purified from column chromatography using CH2Cl2/EtOAc (80:20) to give a solid. This solid was recrystallized from CH2Cl2/hexane to give 55.8 g (73.9%) of (2/?)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2- methylpropanamide as a light-yellow solid. *H NMR (CDC13/TMS) delta 1.66 (s, 3H, CH3), 3.11 (s, 1H, OH), 3.63 (d, / = 10.8 Hz, 1H, CH2), 4.05 (d, / = 10.8 Hz, 1H, CH2), 7.85 (d, / = 8.4 Hz, 1H, ArH), 7.99 (dd, / = 2.1, 8.4 Hz, 1H, ArH), 8.12 (d, / = 2.1 Hz, 1H, ArH), 9.04 (bs, 1Eta, NH). Calculated Mass: 349.99, [Mu-Eta]” 349.0. M.p.: 124-126 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Cyano-3-trifluoromethylaniline, its application will become more common.

Reference:
Patent; GTX, INC.; DALTON, James, T.; GOSNELL, Matthew; WO2013/67170; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, A new synthetic method of this compound is introduced below., name: 4-Cyano-3-trifluoromethylaniline

4-Isocyanato-2-trifluoromethyl-benzonitrile (8a) To a solution of 5-amino-2-cyanobenzotrifluoride (1a) (2.0 g, 10.7 mmol) in ethyl acetate (6 mL) at 0 C. under argon, was added dropwise a 2.0 M solution of phosgene in toluene (6.5 mL, 12.9 mmol). The solution was stirred 30 min at 0 C. and allowed to return at room temperature. Toluene (3 mL) was then added to the ethyl acetate and the resulting solution was refluxed for 3 hrs using a Dean-Stark apparatus, equipped with an HCl trap (solid NaOH). The first 6 mL of distilled solvent was removed and replaced by toluene (6 mL). The solution was then filtrated and evaporated to give compound 8a (1.6 g) as an orange oil which was directly used for the next step. IR: 2268 (strong), 2232 (weak) cm-1.

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; Labrie, Fernand; Breton, Rock; Singh, Shankar Mohan; Maltais, Rene; US2006/287327; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 654-70-6, These common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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.

At 0C,Compound 16a (25.00 g, 134.31 mmol)Liquid bromine (21.68 g, 135.66 mmol) was slowly added dropwise to a solution of methanol (200 mL).The resulting reaction solution was continuously stirred for 0.5 hours.At 0C,Saturated sodium thiosulfate solution (200 mL) was added to the reaction system to quench the reaction, then diluted with water (1000 mL), filtered, and the solid was washed with water (200 mL×3).After drying under reduced pressure, compound 16b (34.30 g) was obtained.

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

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Nanjing Mingde Drug Discovery Co., Ltd.; Yao Yuanshan; Chen Bin; Chen Yuan; Li Ao; Xu Ran; Huang Zhensheng; Tian Dongdong; Li Hongwei; Yang Chengshuai; Li Jian; Chen Shuhui; (30 pag.)CN107954995; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 654-70-6

Synthesis of (2R)-3-Bromo-N-[4-cyano-3-(trifluoromethyl) phenyl]-2-hydroxy-2- methylpropanamide. Thionyl chloride (46.02 g, 0.39 mol) was added dropwise to a cooled solution (less than 4 C) of 6 (51.13 g, 0.28 mol) in 300 mL of THF under an argon atmosphere. The resulting mixture was stirred for 3 h under the same condition. To this was added Et3N (39.14 g, 0.39 mol) and stirred for 20 min under the same condition. After 20 min, 5-amino-2- cyanobenzotrifluoride (40.0 g, 0.21 mol), 400 mL of THF were added and then the mixture was allowed to stir overnight at room temperature. The solvent was removed under reduced pressure to give a solid which was treated with 300 mL of H2O, extracted with EtOAc (2 X 400 mL). The combined organic extracts were washed with saturated NaHCO3 solution (2 X 300 mL) and brine (300 mL). The organic layer was dried over MgSO4 and concentrated under reduced pressure to give a solid which was purified from column chromatography using CH2Cl2ZEtOAc (80:20) to give a solid. This solid was recrystallized from CH2Cl2/hexane to give 55.8 g (73.9%) of (2R)-3- Bromo-N-[4-cyano-3-(trifluoromethyl) phenyl] -2-hydroxy-2-methylpropanamide as a light- yellow solid. 1H NMR (CDC13/TMS) delta 1.66 (s, 3H, CH3), 3.11 (s, 1eta, OH), 3.63 (d, / = 10.8 Hz, IH, CH2), 4.05 (d, / = 10.8 Hz, IH, CH2J, 7.85 (d, / = 8.4 Hz, IH, ArH), 7.99 (dd, / = 2.1, 8.4 Hz, IH, ArH), 8.12 (d, / = 2.1 Hz, IH, ArH), 9.04 (bs, 1eta, NH). Calculated Mass: 349.99, [M-H]- 349.0. M.p.: 124-126 0C.

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

Reference:
Patent; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; AHN, Tai; WO2009/36206; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products 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.

Step 22.3: 4-Amino-2-trifluoromethyl-benzaldehyde A solution of 3 g (0.0161 mol) 4-amino-2-trifluoromethyl-benzonitrile in 9 mL of dry THF is treated dropwise at rt and under nitrogen with 26.85 mL (0.0403 mol) of a 1.5 M diisobutyl-aluminum-hydride solution in toluene. During the addition the temperature is maintained at maximally 28 C. by appropriate cooling. After complete addition the brown solution is allowed to stand at rt over night. It is then added dropwise to a mixture of 4.4 mL of methanol and 39 mL of a saturated (~3M) potassium sodium tartrate solution. During the hydrolysis the temperature is kept below 40 C. After stirring for 15 minutes ethyl acetate is added and the two layers separated. The ethyl acetate phase is washed with water and brine, dried with sodium sulphate and evaporated. The brown foam obtained consists of oligomeric forms of the aldehyde (imine formation) and is therefore re-dissolved in 10 mL of ethyl acetate and stirred efficiently for 10 minutes with 10 mL of 1 N HCl. Sodium hydroxide (1 N, 8.5 mL) is added and stirring is continued for 5 more minutes (at the end the solution has pH ~9). The ethyl acetate is separated, washed with brine, dried with sodium sulphate and evaporated to give crude 4-amino-2-trifluoromethyl-benzaldehyde as a brown oil which is immediately used in the next step.

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

Reference:
Patent; Caravatti, Giorgio; Furet, Pascal; Imbach, Patricia; Martiny-Baron, Georg; Perez, Lawrence Blas; Sheng, Tao; US2006/35897; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 654-70-6 as follows. Formula: C8H5F3N2

Example 43 (General Procedure (D)) 3-Tert-Butyl-5-Chloro-N-(4-Cyano-3-Trifluoromethyl-Phenyl)-2-Hydroxy-6-Methyl-Benzamide. The title compound was prepared from 5-chloro-3-tert-butyl-6-methylsalicylic acid and 4-cyano-3-trifluoromethylanilin. 1H-NMR: (CDCl3, 400 MHz): delta ppm 1.40 (s, 9 H) 2.53 (s, 3 H) 7.39 (s, 1 H) 7.66 (s, 1 H) 7.86 (d, J=8,3 Hz, 1 H) 8.97 (d, J=8,3 Hz, 1 H) 8.05 (s, 1 H) 9.05 (s, 1H).

According to the analysis of related databases, 654-70-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hansen, Birgit Sehested; Hansen, Thomas Kruse; Tullin, Soren; Colding-Jorgensen, Morten; US2004/138301; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H5F3N2

Thionyl chloride (46.02 g, 0.39 mol) was added dropwise to a cooled solution (less than 4C) of (R)-3-bromo-2-hydroxy-2-methylpropanoic acid (4) (51.13 g, 0.28 mol) in 300 mL of THF under an argon atmosphere. The resulting mixture was stirred for 3 h under the same condition. To this was added Et3N (39.14 g, 0.39 mol) and stirred for 20 min under the same condition. After 20 min, 5-amino-2-cyanobenzotrifluoride (40.0 g, 0.21 mol), 400 mL of THF were added and then the mixture was allowed to stir overnight at RT. The solvent was removed under reduced pressure to give a solid which was treated with 300 mL of H2O, extracted with EtOAc (2 × 400 mL). The combined organic extracts were washed with saturated NaHCO3solution (2 × 300 mL) and brine (300 mL). The organic layer was dried over MgSO4and concentrated under reduced pressure to give a solid which was purified from column chromatography using CH2Cl2/EtOAc (80:20) to give a solid. This solid was recrystallized from to give 55.8 g (73.9%) of (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]- 2-hydroxy-2-methylpropanamide (8) as a light-yellow solid. M.p. 134.0-136.5C;1H NMR (CDCl3/TMS) delta 1.66 (s, 3H, CH3), 3.11 (s, 1H, OH), 3.63 (d, J = 10.8 Hz, 1H, CH2), 4.05 (d, J = 10.8 Hz, 1H, CH2), 7.85 (d, J = 8.4 Hz, 1H, ArH), 7.99 (dd, J = 2.1, 8.4 Hz, 1H, ArH), 8.12 (d, J = 2.1 Hz, 1H, ArH), 9.04 (bs, 1H, NH). Calculated Mass: 349.99, [M – H] – 349.0.

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

Reference:
Patent; GTX, INC.; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane D.; PONNUSAMY, Thamarai; HWANG, Dong-Jin; HE, Yali; PAGADALA, Jayaprakash; DUKE, Charles B.; COSS, Christopher C.; DALTON, James T.; (296 pag.)WO2016/172358; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 654-70-6 as follows. Quality Control of 4-Cyano-3-trifluoromethylaniline

4-cyano-3-trifluoromethyl-aniline is reacted with propene-2-sulfonyl chloride (51), and subjected to epoxidation followed by opening of the epoxide ring with p-CN-phenol in the presence of potassium carbonate to yield compound V, as presented in Figure 1 C.

According to the analysis of related databases, 654-70-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OSURF (OHIO STATE UNIVERSITY RESEARCH FOUNDATION); UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; WO2008/11072; (2008); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, A new synthetic method of this compound is introduced below., SDS of cas: 654-70-6

In a 500 mL four necked round bottomed flask equipped with nitrogen atmosphere facility, mechanical stirrer, thermometer and an addition funnel, (15 g) 4-amino-2-(trifluoromethyl)benzonitrile, 150 mL water and 75 mL dichloromethane were added at 20-30 C. The reaction mixture was stirred for 15 min and 9 mL thiophosgene was added. The reaction mixture was stirred for 4 hours. After completion of the reaction, the layers were separated and the organic layer was concentrated completely U/V at 40 C. 105 mL, hexane was added to the concentrated reaction mass and cooled 0 to 5 C. The compound was filtered, washed with hexane and dried to obtain 20 g titled compound with 98% purity by HPLC.

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

Reference:
Patent; Cadila Healthcare Limited; Dwivedi, Shri Prakash Dhar; Singh, Kumar Kamlesh; Charan, Ganpat Dan Shimbhu; (16 pag.)US2017/158643; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 654-70-6, These common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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.

10-Chloro-2-cyclopentyl-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-8,10,12-trien-5-one (Intermediate 1, 157 mg, 0.56 mmol), 4-amino-2-methyl-benzonitrile (Aldrich, 95 mg, 0.51 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (27 mg, 0.05 mmol) were dissolved in 1,4-dioxane (7.5 mL). Caesium carbonate (330 mg, 1.01 mmol) was added and the mixture purged with a stream of nitrogen for 5 minutes. Tris(dibenzylideneacetone) palladium (II) (28 mg, 0.03 mmol) was added and the apparatus was evacuated and backfilled with nitrogen (×3) and then heated at 100 C. for 8 h. The mixture was cooled, filtered and the filtrate absorbed onto an SCX-3 column, washed with methanol and the product eluted with ammonia in methanol. Product containing fractions were concentrated and purified by preparative reverse phase chromatography to give the title compound as a white solid. (21 mg, 10%)1H NMR (399.9 MHz, DMSO-d6) delta1.57-1.72 (6H, m), 1.92-2.00 (2H, m), 2.61 (2H, m), 3.19 (3H, s), 3.64-3.66 (2H, m), 4.82-4.90 (1H, m), 7.99-8.07 (2H, m), 8.16 (1H, s), 8.50 (1H, d), 10.15 (1H, s); MS m/z 431 [M+H]+.

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

Reference:
Patent; ASTRAZENECA AB; US2008/9482; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts