Category: 654-70-6

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. 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. Application In Synthesis of 4-Cyano-3-trifluoromethylaniline

A solution of 2-(2-methoxyethyl)-1 -oxo-3-(thiophen-2-yl)-1 ,2,3,4-tetrahydroisoquinoline-4- carboxylic acid (100 mg, 0.30 mmol) and thionyl chloride (1.5 mL) in chloroform (1 .5 mL) was refluxed for 1 hour. After cooling, the volatiles were removed under reduced pressure. The residue was dissolved in chloroform (1 .5 mL) under nitrogen atmosphere and triethylamine (100 muL) was added. To this solution was added 4-amino-2- (trifluoromethyl)benzonitrile (67 mg, 0.36 mmol) and the stirring was continued at 5O0C for 5 days. The mixture was evaporated under reduced pressure and the crude material was purified by flash chromatography on silica gel using a gradient of ethyl acetate (15 – 70%) in heptane followed by precipitation from a mixture of dichloromethane/heptane afford 23.3 mg (15%) of the titled compound as a tan solid. ESI/APCI(+): 500 (M+H). ESI/APCI(- ): 498 (M-H). 1H NMR (DMSO-c/6) delta 10.38 (1 H, s, NH), 8.31 (1 H, s), 8.14 (1 H, d), 8.04 (1 H, d), 7.94 (1 H, d), 7.52-7.42 (2H, m), 7.37 (1 H, d), 7.32 (1 H, d), 7.02 (1 H, s), 6.93 (1 H, t), 5.62 (1 H, s), 4.39 (1 H, s), 4.14 (1 H, dt), 3.40 (2H, t), 3.08 (1 H, dt), 2.91 (3H, s).

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

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U.LEUVEN R&D; BARDIOT, Dorothee; BLANCHE, Emilie; CHALTIN, Patrick; KOUKNI, Mohamed; LEYSSEN, Pieter; NEYTS, Johan; MARCHAND, Arnaud; VLIEGEN, Inge; WO2010/55164; (2010); A2;,
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Synthetic Route of 654-70-6, 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. 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.

Lithium bis (trimethylsilyl) amide (LHMDS) (5 eq.) was added to a solution of 4-cyano-3-trifluoromethyl aniline (1.6 eq.) in dry THF (1 mL x mmol aniline) at -5C. After stirring for 45 min., hexamethylphosphoric triamide (HMPA) (20% of the previously added, THF) . After 5 min at -5C a solution of (R) -XVIII-5 in THF (1.5 mL x mmol of (.R)-XVIII-S) was added drop wise. After 30 min at 00C, the reaction mixture was allowed to warm up at the temperature value (25C) and than stirred for additional 6/7 h. The reaction was than quenched with an NH4Cl saturated solution and extracted with ethyl acetate. Silica gel column chromatography or crystallization, afforded the pure compound.(R) -XXIV-I: 1H NMR (400 MHz, CDCl3) : bs, IH, NH) , 7.69 (d, J= 8.8Hz, 2H, 7.53-7.48 (m, 3H, ArH) , 7.39-7.26 (m, H) , 6.84 (t, J= 8.2Hz, 2H, ArH) , 3.90(d, J= 14.4Hz, IH, CH2) , 3.78 (bs, IH, OH) , 3.26 (d, J= 13.6Hz, IH, CH2) , 3.07 (d, J= 14.4Hz, IH, CH2) , 2.95 (d, J= 13.2Hz, IH, CH2)

The synthetic route of 4-Cyano-3-trifluoromethylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; ISTITUTO SCIENTIFICO ROMAGNOLO PER LO STUDIO E LA CURA DEI TUMORI (I.R.S.T.) S.R.L.; VARCHI, Greta; TESEI, Anna; GUERRINI, Andrea; BRIGLIADORI, Giovanni; WO2010/116342; (2010); A2;,
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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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-Cyano-3-trifluoromethylaniline

2-ethoxy-6-pentadecyl-benzoyl chloride was condensed with 4-Amino-2-trifluromethyl benzonitrile in dichloromethane in presence of triethylamine as acid scavenger to, yield N-(4-Cyano-3-trifluoromethyl-phenyl)-2-ethoxy-6-pentadecyl-benzamide. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product. m/z: 545.5 (M+1),359.6, 331.6, 213.3, 175.1, 149.1, 107.1,91,55.1

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; Kundu, Tapas Kumar; Balasubramanyam, Karanam; Swaminathan, Vankatesh; US2006/167107; (2006); A1;,
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Reference 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.

To a clear amber solution of 2-trifluoromethyl 4-aminobenzonitrile (14.9 g; 80.8 mmol; 2.0 equiv) in 80 mL dry THF at 22C was added Compound IA (10.0 g; 40.4 mmol; 1.0 equiv), neat, by syringe. A slight exotherm was observed. The homogeneous amber solution stirred for 20 minutes, then placed in a 55C oil bath for 30 minutes. HPLC indicated only a small amount of aniline was present. The contents of the reactor were concentrated in vacuo, yielding a tan solid. After absorption onto silica, the crude material was purified by flash column chromatography (1% acetone/DCM to elute aniline, then 10-50% acetone/DCM to elute desired as a pale yellow band.) 20.3 g (94 %) of Compound IB was obtained as an off-white solid.[00153] 95% at 3.736 min (retention times) (YMC ODS-A column 4.6 x 50 mm eluting with 10-90% aqueous methanol over 4 minutes containing 0.1% H3PO4, 4 mL/min, monitoring at 220 nm).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/59077; (2009); A1;,
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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. Recommanded Product: 654-70-6

To a solution of the acid chloride as prepared in the previous example (2.1 g, 0.0072 moles) in 12 mL of anhydrous toluene is added 0.9 g (0.0072 moles) of DMAP, maintaining the solution at room temperature; the suspension is allowed to react for 10 minutes then 1.15 g (0.0062 moles) of 4-amino-2-trifluoromethyl-benzonitrile dissolved in toluene is added and the mixture is heated at 75-80 C. (external temperature) for 8-10 hours following the disappearance of the amine by TLC (eluent: ethyl acetate/toluene 75/25 or CH2Cl2). After cooling to room temperature the solution is diluted with toluene and treated with a 5% solution of HCl, separated and washed with 5% bicarbonate solution. The organic phase is cured and evaporated under reduced pressure. Crude N-[4-cyano-3-(trifluoromethyl)-phenyl-]-3-[4-fluorophenylthio]-2-acetoxy-2-methyl-propionamide is obtained in quantitative yield as shown by HPLC analysis, NMR spectroscopy and TLC.

The synthetic route of 4-Cyano-3-trifluoromethylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pizzatti, Enrica; Vigano, Enrico; Lussana, Massimiliano; Landonio, Ernesto; US2006/41161; (2006); 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. 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. Product Details of 654-70-6

To a nitrogen flushed, 30-L kettle was charged aniline E (4.0 kg, 21.49 mol) followed by w-heptane (9 L, 2.25 vol) and H20 (10 L, 2.5 vol). The mixture was then agitated for 8 min, cooled to 5-10 C and thiophosgene (1.81 L, 2.72 kg, 23.64 mol, 1.1 equiv) was charged over 12 min, maintaining the batch temperature at 10-16 C, followed by an w-heptane (1 L, 0.25 vol) rinse. The resulting orange slurry was then warmed to 30-40 C over 1.5 h and a slight exotherm to a maximum temperature of 46.4 C was observed. After stirring for 15 h, the orange solution was sampled (>99% conversion). The batch was then heated to 36 C and the phases were allowed to separate. A rag layer was observed and most of it was purged with the bottom aqueous layer. In two portions, w-heptane (18 L, 4.5 vol) was next charged to the orange heptane layer and the solution was distilled to 1.5 vol (45-46 C, 160 mbar). The solution was diluted once more with w-heptane (8 L, 2 vol) and the batch was distilled to 1.5 vol (45-46 C, 160 mbar). The solution was then diluted with w-heptane (10 L, 2.5 vol), cooled to 30-31 C (heptane:product F, 5.3:1) and seeded with product F (10 g). Crystallization was visible within 2-3 min after seeding and the slurry was further cooled to 0-10 C over 3 h and held at 0-10 C for 2 h. The batch was then filtered, rinsed with filtrate and cold w-heptane (4 L, 1 vol) and dried at 20-25 C, under vacuum, for 13 h to yield product F (4.51 kg, 92%), with an HPLC purity of >99%, and a moisture level of 0.04%.

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

Reference:
Patent; MEDIVATION PROSTATE THERAPEUTICS, INC.; JAIN, Rajendra, Parasmal; ANGELAUD, Remy; THOMPSON, Andrew; LAMBERSON, Carol; GREENFIELD, Scott; WO2011/106570; (2011); A1;,
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Electric Literature 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.

20L three-necked flask by adding 5.94L water, 270mL thiophosgene, the temperature control in the 20 ~ 30C ,457 g of 4-amino-2- (trifluoromethyl) benzonitrile was added portionwise under stirring,After the addition, the reaction was continued for 1 h. The reaction was complete by TLC method, extracted with dichloromethane (1 L x 3)The organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated, added with petroleum ether beating,Through liquid nitrogen crystallization, filtration, drying, the product 500g, yield 89.3%.

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

Reference:
Patent; Shanghai DingYa Pharmaceutical Chemicals Co.,Ltd; Ruan, Shiwen; Yan, Haiyan; Xia, Hongfei; Xu, LiPing; (6 pag.)CN104016924; (2016); B;,
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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

General procedure: A substituted aniline (5.0 mmol) and triethylamine (1.87 g,18.5 mmol) were dissolved by dichloromethane (10 mL),and stirred under an ice-water bath, to which chloroacetylchloride (1.29 g, 11.5 mmol) was added dropwise. Afteraddition, the reaction mixture was stirred for one more hourat room temperature, then EA (30 mL) and H2O (30 mL)were added for an extraction. The organic contract waswashed with water (15 mL × 3) and saturated brine (15 mL),dried over Na2SO4 and evaporated under reduced pressureto afford intermediate 5.

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

Reference:
Article; Dong, Junze; Zhang, Jingya; Li, Zilu; Asnake, Solomon; Zhang, Daoguang; Olsson, Per-Erik; Zhao, Guisen; Medicinal Chemistry Research; vol. 28; 3; (2019); p. 380 – 386;,
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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.

Reaction in toluene between 2-acetoxy-2-methyl-3-(4-fluorophenylthio) propionic acid (intermediate ?acetylacid?) and thionyl chloride to give the intermediate 2-acetoxy-2-methyl-3-(4-fluorophenylthio) propionyl chloride (intermediate ?chloride?). The successive reaction of this intermediate (still in toluene) with 4-cyano-3-trifluoromethyl aniline (in the presence of 4-dimethylamino pyridine) to give N-[4-cyano-3-(trifluoromethyl)-phenyl-]-3-[4-fluorophenylthio]-2-acetoxy-2-methyl-propionamide (intermediate ?acetylsulfide?). Evaporation of the toluene and use of the residual oil in the following step.

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; Pizzatti, Enrica; Vigano, Enrico; Lussana, Massimiliano; Landonio, Ernesto; US2006/41161; (2006); A1;,
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Related Products 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.

EXAMPLE 1 Thionyl chloride (0.6 ml.) was added to a stirred solution of 2-hydroxy-2-methyl-3-phenylthiopropionic acid (1.7 g.) in N,N-dimethylacetamide (40 ml.) which was cooled to -15 C., at such a rate that that temperature was maintained, and the mixture was stirred at that temperature for 15 minutes. 4-Cyano-3-trifluoromethylaniline (1.5 g.) was added, the mixture was stirred at -15 C. for 30 minutes and then at laboratory temperature for 15 hours, and was then poured into water (800 ml.). The mixture was extracted six times with diethyl ether (80 ml. each time) and the combined extracts were washed successively (50 ml. portions each time) twice with aqueous 3N-hydrochloric acid, once with saturated aqueous sodium chloride solution, twice with saturated aqueous sodium bicarbonate solution, and again once with saturated aqueous sodium chloride solution, dried over magnesium sulphate and evaporated to dryness under reduced pressure. The residue was purified by chromatography on a silica gel column (Merck 7734) using methylene chloride as eluant. The product was crystallized from a 5:1 v/v mixture of toluene and petroleum ether (b.p. 60-80 C.) and there was thus obtained 4-cyano-3-trifluoromethyl-N-(2-hydroxy-2-methyl-3-phenylthiopropionyl)aniline, m.p. 81.5-83 C.

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

Reference:
Patent; Imperial Chemical Industries PLC; US4636505; (1987); A;,
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