Category: 654-70-6

Application 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.

To a slurry of 4-amino-2- (trifluoromethyl) benzonitrile (30.09 g, 162 mmol) and NaBH3CN (21.35 g, 340 mmol) in CH2CI2 (160 mL) at ice bath temperature was added neat TFA (160 mL, 2.08 mol), dropwise at a rate such that the internal temperature remained below 5C (CAUTION : exothermic reaction with hydrogen gas evolution). TRIFLUOROACETALDEHYDE hydrate (52.2 g, 405 MMOL) was then added over 5 minutes (CAUTION : slightly exothermic reaction, with gas evolution). After 41 h, the mixture was slowly poured into satd NAHC03 (1 L) at 0C. The mixture was then completely neutralized by portionwise addition of solid NAHC03. The mixture was stirred 30 min and precipitated solids were collected by filtration. Organic and aqueous phases of the filtrate were separated, and the aqueous layer extracted with CH2CI2 (3 X 150 mL). Combined organic extracts were concentrated to dryness, combined with the solids collected previously, dissolved in EtOAc, washed (H20, brine), dried over NA2SO4, filtered through a short pad of Celite, and concentrated to dryness. The residue was filtered through a pad of silica gel (EtOAc/hexanes) and concentrated to dryness. Recrystallization from EtOAc/hexanes yielded 32.61 g of the title compound as slightly tan crystalline plates, mp 132. 5-134C :’H NMR (300 MHz, MeOH-d4) 8 7.59 (d, J = 8. 8 Hz, 1 H), 7.05 (d, J = 2.2 Hz, 1 H), 6.92 (dd, J = 8.7, 2.4 Hz, 1 H), 3.92 (q, J = 9.2 Hz, 2H).

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

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/795; (2005); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 654-70-6, A common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, molecular formula is C8H5F3N2, 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.

Thionyl chloride (2.4 ml, 33.6 mmol) was added dropwise to (R)-3-bromo-2-hydroxy-2-methylpropionic acid (5.11).Gram, 28 mmol) in a solution of 30 ml of THF,The temperature of the drop is controlled at 0-12 C.It takes 10 minutes.The resulting mixture was stirred under the same conditions for 2 hours.The internal temperature was adjusted to about -5 C, and triethylamine (Et3N) (5.0 ml, 36.4 mmol, 1.3 eq) was slowly added to the reaction mixture, and the internal temperature was lower than 12 C during the addition.Stir for 20 minutes under the same reaction conditions.Then, a solution of 4-cyano-3-trifluoromethyl-phenylamine (4.0 g, 21 mmol) in 40 mL of THF was added dropwise, and the mixture was stirred at 50 C for two hours.The reaction solution was cooled to 20 ± 5 C, then water (15 ml, 2.9 vol) and toluene (20 ml, 4.0 vol) was added, and after stirring, the mixture was separated and the organic phase was washed with water (15 ml, 2.9 vol.). After the combination, it was concentrated to 5 ± 0.5 volume (6.4% by weight) by distillation under reduced pressure, and the temperature was kept below 50 C during the distillation. Add toluene (31 ml, 6 volumes) to the concentrate, dilute to 5 ± 0.5 volume (6.4 wt), adjust the temperature to 2.5 ± 2.5 C, stir at this temperature for one hour, add seed crystal (0.018 g, 0.005 wt) Stirring was continued for one hour, filtered, and the filter cake was washed twice with toluene (8.5 ml each time, 1.7 volumes each time). The batch is then dried in a vacuum oven.Get 5.8 grams(R)-3-Bromo-N-(4-cyano-3-trifluoromethyl-phenyl)-2-hydroxy-2-methylpropanamide.Yield 59%, HPLC (mobile phase is water and acetonitrile) purity 99% (220 nm), 99% (254 nm), optical HPLC purity 99%.

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; Yang Guohong; He Junze; Duan Meijuan; (34 pag.)CN108558760; (2018); A;,
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.

687 g of 4-amino-2-(trifluoromethyl)benzonitrile with 311 mul of thiophosgene in 4 ml of N,N-dimethylformamide was stirred for one hour at room temperature under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate, washed with water and then concentrated by evaporation in a vacuum. The thus obtained crude isothiocyanate was combined with the cyanoamine that was produced and filtered by two hours of stirring from 743 mul of acetone cyanohydrin with 930 mg of 1,1-dimethylethyl 4-(2-aminoethyl)piperazine-1-carboxylate and 406 mg of a molecular sieve 3 A in 20 ml of tetrahydrofuran at room temperature, and it was heated to boiling for one hour with 0.57 ml of triethylamine in 40 ml of tetrahydrofuran. After concentration by evaporation in a vacuum, the title compound was obtained as a crude product, which was immediately further reacted.

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; Schering AG; US2004/9969; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 654-70-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 654-70-6 name is 4-Cyano-3-trifluoromethylaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

1) Preparation of 4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile (1.1) Compound 1.1 can be prepared by process “A”. To this end, 14.74 g (79.21 mmol) of 4-amino-2-trifluoromethylbenzonitrile were dissolved in 200 ml of dry acetonitrile. This solution was added dropwise with stirring to a 20% solution, heated to 70 C., of phosgene in toluene and then stirred for 1 h. The cooled reaction solution was concentrated under reduced pressure, and the residue was taken up with toluene and concentrated again under reduced pressure. Finally, the residue was dissolved in 150 ml of dry acetonitrile and the solution was admixed with 15.5 g (79.21 mmol) of tert-butyl 2-amino-2-methylpropionate hydrochloride with stirring. 12.02 g (118.8 mmol) of triethylamine were slowly added dropwise to the reaction mixture which was then stirred at room temperature for 45 min. Thereafter, the mixture was admixed cautiously with 50 ml of concentrated hydrochloric acid and stirred at 70 C. for 1 h. The cooled reaction mixture was concentrated under reduced pressure and the residue was admixed with ethyl acetate and water. The organic phase was removed, washed with saturated sodium carbonate solution and then with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel with 2:1 heptane/ethyl acetate. 21.2 g (90% yield) of 4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile 1.1 with the melting point of 208-211 C. were obtained. ; 1) Preparation of 4-(2,4-dioxo-1,3-diazaspiro[4.5]dec-3-yl)-2-trifluoromethylbenzonitrile (28.1) Compound 28.1 can be prepared by process “A”. To this end, 5.3 ml of phosgene solution (20% in toluene) were initially charged under argon atmosphere. At 75 C., a solution of 4-cyano-3-trifluoromethylaniline in 15 ml of dry acetonitrile was slowly added dropwise. After the addition had ended, the mixture was stirred at 75 C. for another 90 min. The mixture was concentrated under reduced pressure. The residue was then taken up repeatedly in toluene and concentrated again under reduced pressure. Finally, the residue was dissolved in 15 ml of dry tetrahydrofuran, admixed with 0.72 g of 1-amino-1-cyclohexanecarboxylic acid and dropwise with 1.05 ml of triethylamine, and the mixture was stirred at room temperature for 2 h. After standing overnight at room temperature, the reaction mixture was admixed with 5 ml of concentrated hydrochloric acid and stirred under reflux for 2 h. The cooled reaction mixture was admixed with saturated sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. 0.62 g of 4-(2,4-dioxo-1,3-diazaspiro[4.5]dec-3-yl)-2-trifluoromethylbenzonitrile (28.1) was obtained. 1H NMR: 9.21, s, 1H, 8.30, d, 1H, 8.19, s, 1H, 8.02, d, 1H, 1.8-1.5, m, 9H, 1.4-1.25, m, 1H.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Cyano-3-trifluoromethylaniline, and friends who are interested can also refer to it.

Reference:
Patent; SANOFI-AVENTIS; US2009/215728; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

654-70-6, name is 4-Cyano-3-trifluoromethylaniline, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 654-70-6

General procedure: A solution of NaHCO3 (0.82 g) in distilled water (4 mL) wasstirred for 10 min and to it was added DCM (4 mL) followed by thedifferent aniline 7e12 (2.4 mmol). The reaction mixture was cooledto 0 C, thiophosgene (0.3 mL, 3.7 mmol) was added dropwise over10 min and the reaction was then stirred at r.t. overnight. Themixture was then diluted with DCM (20 mL), washed with brine(20 mL), the organic layer was dried over Na2SO4 and concentratedto dryness.

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

Reference:
Article; Pertusati, Fabrizio; Ferla, Salvatore; Bassetto, Marcella; Brancale, Andrea; Khandil; Westwell, Andrew D.; McGuigan, Christopher; European Journal of Medicinal Chemistry; vol. 180; (2019); p. 1 – 14;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. Safety of 4-Cyano-3-trifluoromethylaniline

At 0 C, liquid bromine (21.68 g, 135.66 mmol) was slowly added dropwise to a solution of Compound 36a (25.00 g, 134.31 mmol) in methanol (200 mL). After the resulting reaction mixture was further stirred for 0.5 hr, a saturated solution of sodium thiosulfate (200 mL) was added to the reaction system at 0 C to quench the reaction. The resulting mixture was diluted with water (1000 mL), and filtered. The filter cake was washed with water (200 mL×3), and dried under reduced pressure to give Compound 36b (34.30 g). 1H NMR (400 MHz, DMSO-d6) delta8.14 (s, 1H), 7.20 (s, 1H), 6.90 (brs, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 654-70-6, its application will become more common.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; CHEN, Bin; YAO, Yuanshan; CHEN, Yuan; LI, Ao; XU, Ran; HUANG, Zhensheng; TIAN, Dongdong; LI, Hongwei; YANG, Chengshuai; LI, Jian; CHEN, Shuhui; (69 pag.)EP3489235; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 654-70-6, The chemical industry reduces the impact on the environment during synthesis 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, I believe this compound will play a more active role in future production and life.

A. 4-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-2-trifluoromethyl-benzonitrile (471A) A mixture of 3-trifluoromethyl-4-cyano-aniline (24.0 g, 129 mmol) and maleic anhydride (14.0 g, 143 mmol) in 50 mL of acetic acid was heated at 115 C. overnight. A precipitate was obtained during the heating period. The reaction was allowed to stand at rt for an additional overnight period. The solid was removed by filtration, the filter cake was washed with diethyl ether and dried to give 21 g (79 mmol, 61%) of compound 471A as an off white solid. HPLC: 100% at 2.11 min (retention time) (YMC S5 ODS column, 4.6*50 mm, eluding with 10-90% aqueous methanol over 4 min containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm).

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, 4-Cyano-3-trifluoromethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Salvati, Mark E.; Balog, James Aaron; Pickering, Dacia A.; Giese, Soren; Fura, Aberra; Li, Wenying; Patel, Ramesh N.; Hanson, Ronald L.; Mitt, Toomas; Roberge, Jacques Y.; Corte, James R.; Spergel, Steven H.; Rampulla, Richard A.; Misra, Raj N.; Xiao, Hai-Yun; US2004/77605; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 654-70-6, Product Details of 654-70-6

Compound S-III(30.0 g, 164 mmol), 4-cyano-3-trifluoromethylaniline (33.9 g, 182 mmol)Add N, N-methylacetamide (210 mL) to the reaction flask and cool to -15 C in an ice bath.Thionyl chloride (23.0 g, 195 mmol) was added dropwise, and the reaction temperature was controlled to be -10 C to -15 C.After the addition, the mixture was stirred for 0.5 h, and raised to 40 C for 2 h. Pour the reaction solution slowly It was extracted with ethyl acetate (200 mL×3) in cold saturated sodium bicarbonate (60 mL).The organic phase was combined, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and filtered.Concentrate to dryness under reduced pressure to give a crude material eluting with petroleum ether and methyl tert-butyl ether Recrystallization of the solution, decolorization of activated carbon, giving a white solidS-IV 42.3 g, yield 73.1%

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Shijiazhuang Du Zhi Pharmaceutical Technology Co., Ltd.; Fang Yu; Du Yumin; (10 pag.)CN109761778; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 654-70-6, Quality Control of 4-Cyano-3-trifluoromethylaniline

[003 19j 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 (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 mm under the same condition. After 20mm, 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 H20, extracted with EtOAc (2 x400 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 togive a solid which was purified from column chromatography using CH2CWEtOAc (80:20) to give a solid. This solid was recrystallized from CH2CWhexane to give 55.8 g (73.9%) of (2R)-3-bromo- N-[4-cyano-3 -(trifluoromethyl)phenylj -2-hydroxy-2-methylpropanamide as a light-yellow solid. Mp 134.0-136.5C;[00320j ?H NMR (CDC13fFMS) oe 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, Ar]), 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). MS (ESI) 349.0 [M – Hj M.p.: 124- 126C.

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, 4-Cyano-3-trifluoromethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GTX, INC.; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane D.; PONNUSAMY, Thamarai; HWANG, Dong-Jin; DUKE, Charles B.; COSS, Christopher C.; JONES, Amanda; DALTON, James T.; (159 pag.)WO2016/172330; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 654-70-6, 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.

4-Amino-2-trifluoromethylbenzonitrile, (2.23 g, 12 mmol) was added portionwise over15 minutes into the well-stirred heterogeneous mixture of thiophosgene (1 ml, 13 mmol) in water (22 ml) at room temperature. Stirring was continued for an additional 1 h. The reaction medium was extracted with chloroform (3 x 15 ml). The combined organic phase was dried over MgSO4 and evaporated to dryness under reduced pressure to yield desired product, 4-isothiocyanato-2-trifluoromethylbenzonitrile, (Ia), as brownish solid and was used as such for the next step (2.72 g, 11.9 mmol, 99%).

The chemical industry reduces the impact on the environment during synthesis 4-Cyano-3-trifluoromethylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; WO2006/124118; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts