Month: July 2021

Synthetic Route of 123-06-8, 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. 123-06-8, name is Ethoxymethylenemalononitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 2-(ethoxymethylene)propanedinitrile (20 g, 163.80 mmol) was added hydrazine hydrate (15.9 mL, 327.60 mmol) dropwise at 0 C and the resultant reaction mixture was heated at 100 C in a closed reagent bottle for 1h. The reaction was monitored by TLC. After completion, the reaction mixture was cooled to RT and water (50 mL) was added. The product was extracted using EtOAc (3×200 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 15 g of 5- amino-1H-pyrazole-4-carbonitrile as a light brown solid.

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

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; RAI, Roopa; CHAKRAVARTY, Sarvajit; GREEN, Michael, John; PHAM, Son, Minh; PUJALA, Brahmam; AGARWAL, Anil, Kumar; NAYAK, Ajan, Kumar; KHARE, Sweta; GUGULOTH, Rambabu; RANDIVE, Nitin, Atmaram; WO2015/69441; (2015); A1;,
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Related Products of 25808-30-4,Some common heterocyclic compound, 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, molecular formula is C3H7ClN2, 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. N-Carbethoxy-N-methylaminoacetonitrile Triethylamine (5.2 ml; 37.6 mmoles) was added to a suspension of methylaminoacetonitrile hydrochloride (2.0 g; 18.8 mmoles) in 20 ml of methylene chloride. The resulting suspension was cooled in an ice-bath and a solution of ethyl chloroformate (2.14 g; 19.8 mmoles) in 10 ml of methylene chloride was added over a 0.5 hour period, and the mixture was then heated at reflux temperature for 18 hours. The reaction mixture was evaporated under reduced pressure to give a semi-solid residue which was triturated with diethyl ether and filtered, and the filtrate was evaporated under reduced pressure to yield the title compound as an oil (2.2 g), bp 96°-98°/5.2 mm Hg.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Methylamino)acetonitrile hydrochloride, its application will become more common.

Reference:
Patent; Bristol-Myers Company; US4471122; (1984); A;; ; Patent; Bristol-Myers Company; US4510309; (1985); A;; ; Patent; Bristol-Myers Company; US4394508; (1983); A;,
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Adding a certain compound to certain chemical reactions, such as: 49674-15-9, name is 3-Bromo-5-nitrobenzonitrile, 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 49674-15-9, HPLC of Formula: C7H3BrN2O2

General procedure: To a solution of 6 (500 mg, 2.64 mmol) in 10 mL of DMF was successively added Et3N (1.47 mL, 10.56 mmol), 9a (600 mg, 2.64 mmol), CuI (50 mg, 0.26 mmol), and trans-dichlorobis(triphenylphosphine)palladium (184 mg, 0.26 mmol). The resulting solution was warmed to 60 oC, and TBAF 1M in THF (2.9 ml, 2.90mmol) was added dropwise. After 2h at this temperature the mixture was hydrolyzed with 50 mL of H2O and, extracted with AcOEt (4 X 30 mL). The organic layer was washed with saturated NaCl (3 X 30 mL), dry over anhydrous Na2SO4, and concentrated on a rotary evaporator. Purification of the residue by column chromatography (hexane/AcOEt 8/2) yielded 473 mg (68 %) of 2a as an off white solid.1H NMR (CDCl3), d = 2.50 (s, 3H, CH3); 7.13 (d, 1H, J=7.6 Hz, CHAr); 7.32 (d, 1H, J=7.6 Hz, CHAr); 7.56 (t, 1H, J=7.6 Hz, CHAr); 8.04 (t, 1H, J=1.6 Hz, CHAr); 8.35 (t, 1H, J=1.6 Hz, CHAr); 8.52 (t, 1H, J=1.6 Hz, CHAr). 13C NMR (CDCl3), d = 24.5 (1C, CH3); 83.4 (1C, C?C); 93.6 (1C, C?C); 114.4 (1C, Cq); 115.9 (1C, Cq); 124.4 (1C, CHAr); 124.9 (1C, CHAr); 126.1 (1C, Cq); 126.4 (1C, CHAr); 130.3 (1C, CHAr); 136.7 (1C, CHAr); 140.1 (1C, CHAr); 140.7 (1C, Cq); 148.1 (1C, Cq); 159.5 (1C, Cq). Anal (C15H9N3O2, HCl) C, H, N.

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, 3-Bromo-5-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Alagille, David; Dacosta, Herve; Chen, Yelin; Hemstapat, Kamondanai; Rodriguez, Alice; Baldwin, Ronald M.; Conn, Jeffrey P.; Tamagnan, Gilles D.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 11; (2011); p. 3243 – 3247;,
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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 16588-02-6 as follows. Formula: C7H3ClN2O2

2-(Benzylthio)-5-nitrobenzonitrile[0294] To a solution of 2-chloro-5-nitrobenzonitrile (27.375 g, 0.15 mol) in MeCN (500 ml) was added K2C03 (24.84 g, 0.18 mol) and phenylmethanethiol (17.71 ml, 0.15 mol). The solution was stirred at room temperature for overnight. The mixture was filtered through the celite pad and the filtrate was concentrated in vacuo to give 2-(benzylthio)-5-nitrobenzonitrile (40.5 g, 100%) as a yellow solid. 1H NMR: CDC13400 MHz 58.43 (s, 1H), 8.27-8.25 (m, 1H), 7.44-7.31 (m, 6H), 4.35 (s, 2H).

According to the analysis of related databases, 16588-02-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; HERNANDEZ, Vincent, S.; LI, Xianfeng; ZHANG, Suoming; AKAMA, Tsutomu; ZHANG, Yanchen; LIU, Yang; PLATTNER, Jacob, J.; ALLEY, Michael, Kevin Richard; ZHOU, Yasheen; NEIMAN, James, A.; WO2011/60196; (2011); A1;,
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Synthetic Route of 3441-01-8, 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 3441-01-8 as follows.

To a stirred solution of 2-((6-bromopyridin-3-yl)(methoxy)methyl)-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridine (200 mg, 0.517 mmol) in THF (5 mL) were added 3-cyanobenzamide (113 mg, 0.775 mmol) and sodium 2-methylpropan-2-olate (99 mg, 1.0 mmol), Brettphos Pd G3 (47 mg, 0.052 mmol) at RT. After the addition was finished, the reaction was stirred at 60 °C for 16 h. The reaction was diluted with water, extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04i filtered and concentrated in vacuo to afford a residue, which was purified by reversed phase HPLC, eluting with water (0.1 percentTFA)-ACN to afford the title compound as a TF A salt (Ex. 39). XH NMR (400 MHz, CD3OD) delta 8.67 (s, 1 H), 8.52 (d, J=1.8 Hz, 1 H), 8.32 (t, J=1.4 Hz, 1 H), 8.28 – 8.24 (m, 3 H), 7.96-7.94 (m, 2 H), 7.74-7.72 (m, 1 H),5.77(s, 1 H), 3.54 (s, 3 H); MS (EI) m/z: 453 [M+H]+.

According to the analysis of related databases, 3441-01-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Hua; FRADERA, Xavier; HAN, Yongxin; MCGOWAN, Meredeth, A.; SCIAMMETTA, Nunzio; WHITE, Catherine; YU, Wensheng; (89 pag.)WO2019/27856; (2019); A1;,
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Electric Literature of 939-79-7, A common heterocyclic compound, 939-79-7, name is 4-Methyl-3-nitrobenzonitrile, molecular formula is C8H6N2O2, 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.

A mixture of 0.32 g of 3-nitro-4-methyl-benzonitrile (1; 0.32 g, 2.0 mmol), 3-fluoro-4-bromo-benzaldehyde (35; 0.40 g, 2.0mmol), piperidine (0.1 mL, 1.0 mmol) and sulfolane (3 g) was heated in a sealed tube at 150-160 C for 1 h. After cooling to room temperature, water (10 mL) was added. The resulting precipitate was filtered and dried under high vacuum to provide 0.64 g (94%) of product as yellow solid.

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:
Article; Nguyen, Son T.; Williams, John D.; Butler, Michelle M.; Ding, Xiaoyuan; Mills, Debra M.; Tashjian, Tommy F.; Panchal, Rekha G.; Weir, Susan K.; Moon, Chaeho; Kim, Hwa-Ok; Marsden, Jeremiah A.; Peet, Norton P.; Bowlin, Terry L.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3366 – 3372;,
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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. 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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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 63069-50-1 as follows. Recommanded Product: 4-Amino-3-fluorobenzonitrile

General procedure: A round-bottomed flask was charged with 2-bromoaniline or 2-fluoro-aniline (>3 g, 1.0 equiv) and potassium O-ethyl carbonodithioate(1.5-1.7 equiv). The mixture was dissolved in DMF (10 volumes) andheated to 120-130 C until the aniline was fully consumed (3-14 h).The reaction mixture was cooled to r.t. and filtered. The filtrate wasdiluted with H 2 O (50 volumes) and the pH was adjusted to 1-2 usingaqueous 2 M HCl. The solid precipitate was collected, washed withH 2 O and dried to yield the pure product.

According to the analysis of related databases, 63069-50-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wimmer, Laurin; Parmentier, Michael; Riss, Bernard; Kapferer, Tobias; Ye, Chao; Li, Lei; Kim, Hongyong; Li, Jialiang; Synthesis; vol. 50; 10; (2018); p. 2027 – 2032;,
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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. 21524-39-0, name is 2,3-Difluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 2,3-Difluorobenzonitrile

To a solution of 1,1-dioxo-1?6-[1,2]thiazin-2-ane (1.90 g, 14.4 mmol) dissolved in tetrahydrofuran (8 mL) and dimethylformamide (2 mL) was added sodium hydride (0.36 g, 95%, 14.4 mmol) and the mixture stirred for 20 min. To this was added 2,3-difluorobenzonitrile (2.0 g, 14.4 mmol) and the mixture stirred at 90 C. for 2 h. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with water and brine then concentrated. The solid residue was triturated with 1:1 ethyl acetate/hexane to give the title compound as a pale brown solid (0.47 g, 13% yield). 1H-NMR (500 MHz, CDCl3) ? ppm: 7.47-7.45 (1H, m), 7.32-7.36 (2H, m), 4.08-4.02 (1H, m), 3.57 (1H, td, J=13.0, 3,7 Hz), 3.40-3.34 (1H, m), 3.32-3.27 (1H, m), 2.44-2.32 (2HF, m), 2.04-1.97 (2H, m), 1.90-1.84 (1H, m). LCMS [M+H]+ calcd for C11H12N2FO2S: 255.28; found: 255.13.

The synthetic route of 21524-39-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Naidu, B. Narasimhulu; Banville, Jacques; Beaulieu, Francis; Connolly, Timothy P.; Krystal, Mark R.; Matiskella, John D.; Ouellet, Carl; Plamondon, Serge; Remillard, Roger; Sorenson, Margaret E.; Ueda, Yasutsugu; Walker, Michael A.; US2005/267105; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, 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 67515-59-7, Computed Properties of C8H3F4N

To a mixture of the compound of Preparation 9 (150 mg, 0.5 mmol) and 4-fluoro-3-(trifluoromethyl)benzonitrile (86 mg, 0.5 mmol), under nitrogen, was added tetrahydrofuran (2 ml). The mixture was cooled to 0 C., before the dropwise addition of potassium tert-butoxide (1M in tetrahydrofuran, 0.8 ml, 0.8 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 19 h. The mixture was diluted with ethyl acetate and washed with saturated aqueous ammonium chloride solution (×2), water and brine, dried (MgSO4) and concentrated in vacuo. The residue was dissolved in methanol (2 ml) and purified by automated preparative liquid chromatography (Gilson system, 150 mm×50 mm LUNA C18(2) 10 mum column, 120 ml/min) using an acetonitrile:water gradient [55:45 (for 15 min) to 98:2 (for 3 min) to 55:45 (for 1 min)]. The appropriate fractions were concentrated in vacuo to give the compound of Example 3a (73 mg) as a racemic mixture.Experimental MH+ 499.9; expected 500.11H-NMR (d6-Acetone): 1.98-2.00 (3H), 4.78-4.80 (1H), 4.84-4.86 (1H), 7.58-7.60 (1H), 8.00-8.03 (2H), 8.08-8.12 (4H)in vitro H.c. (L3) MED=1 mug/ml

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-Fluoro-3-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER LIMITED; US2008/194694; (2008); A1;,
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