Tag: M.W=200-300

Related Products of 20099-89-2, A common heterocyclic compound, 20099-89-2, name is 4-(2-Bromoacetyl)benzonitrile, molecular formula is C9H6BrNO, 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) 4-(2-Oxiranyl)benzonitrile NaBH4 (1.6 g; 40 mmol) was added to a stirred solution of 4-cyanophenacyl bromide (8.8 g; 40 mmol) in THF (100 mL), and the reaction mixture was stirred until tic indicated that the reaction was complete. The solvent was evaporated and the residue partitioned between DCM and H2O, and the organic layer was separated, dried and concentrated. The residue was treated with K2CO3 (0.08 mol) in MeCN (85 mL) at room temperature overnight. The solvent was removed on a rotary evaporator and the residue partitioned between CH2Cl2 and H2O. The organic layer was washed with H2O (2*100 mL), separated and dried to give the sub-title compound in 90% overall yield.

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; AstraZeneca AB; US6291475; (2001); B1;,
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Adding a certain compound to certain chemical reactions, such as: 330793-38-9, name is 4-Bromo-2-methoxybenzonitrile, 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 330793-38-9, SDS of cas: 330793-38-9

A mixture of 3,3-dimethylindolin-2-one (31) (12.9 mg, 0.08 mmol), 4-bromo-2-methoxybenzonitrile (30) (17.0 mg, 0.08 mmol), COPPER (I) IODIDE (7.80 mg, 0.04 mmol), TRANS- (1R, 2R)- N, N’- DIMETHYL- CYCLOHEXANE- 1, 2- DIAMINE (11.7 mg, 0.08 mmol) and POTASSIUM PHOSPHATE (35.0 mg, 0.16 mmol) in DMSO (0.50 mL) was heated to 80C for 1.5 h, then heated to 100C for 21h. The reaction mixture was diluted with ethyl acetate, filtered through a plug of silica gel and concentrated by rotary evaporation. The resulting residue was purified by prep-HPLC to afford 4-(3,3-dimethyl-2-oxoindolin-1-yl)-2-methoxybenzonitrile (32) (8.75 mg, 37percent). 1H NMR (500 MHz, DMSO-d6) d ppm 1.41 (s, 6 H) 3.95 (s, 3 H) 6.95 (d, J=7.81 Hz, 1 H) 7.14 (t, J=7.32 Hz, 1 H) 7.20 (d, J=7.81 Hz, 1 H) 7.24 (t, J=7.81 Hz, 1 H) 7.36 (s, 1 H) 7.46 (d, J=6.83 Hz, 1 H) 7.90 (d, J=7.81 Hz, 1 H)

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:
Article; Guo, Chuangxing; Pairish, Mason; Linton, Angelica; Kephart, Susan; Ornelas, Martha; Nagata, Asako; Burke, Benjamin; Dong, Liming; Engebretsen, Jon; Fanjul, Andrea N.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 7; (2012); p. 2572 – 2578;,
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Electric Literature of 1813-33-8,Some common heterocyclic compound, 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, molecular formula is C8H3ClF3N, 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.

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate amine (NR2, 2.00 mmol),and DBU (2.5 mmol) were dissolved in 1,4-dioxane (8 ml). Themixture was stirred for 12 h at 50 C. The reaction was quenched with water and extracted with EtOAc twice. The combined organicextracts were dried over MgSO4, filtered, and concentrated invacuo. The residue was purified by flash column chromatographyon silica gel using EtOAc/hexane (1:7-1:10) eluant condition.(NR2 = 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloridefor 17).

The synthetic route of 1813-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
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Electric Literature of 77668-42-9, A common heterocyclic compound, 77668-42-9, name is 2,3-Dichlorobenzoyl cyanide, molecular formula is C8H3Cl2NO, 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.

In the reactor was added 40g aminoguanidine carbonate and 200ml of methanol (entrainer)30g concentrated sulfuric acid was added dropwise with stirring, the addition was completed dropwise distillation entrainer,And bring out the water, suction filtration,Solid into the reaction flask, at 80 C under reduced pressure and drained.Adding 2,3-dichlorobenzoyl cyanide solution obtained in step (1), heating to 80 C., reacting for 3 h to the end of the reaction, lowering to room temperature, and filtering by suction to obtain white sand particles;

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; Zhejiang Qicai Environment Technology Co., Ltd.; Jin Cheng; Chen Lina; Liang Wei; Zhang Tong; Chen Lei; (6 pag.)CN106083753; (2016); A;,
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Synthetic Route of 13338-63-1, 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. 13338-63-1, name is 3,4,5-Trimethoxyphenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Using the method of synthesizing an intermediate similar to that of Example 1,Take 3,4,5-trimethoxyphenylacetonitrile (5) 0.01 mol, 0.01 mol of 3-fluorobenzaldehyde and 20 mL of methanol into a 50 mL three-necked flask.Stirring to 60 C, adding 0.005 mol of sodium methoxide, constant temperature reaction 4-6 h,TLC scanning and detection, after the reaction is completed, it is cooled to room temperature, filtered, washed with water, dried, and recrystallized from methanol to obtain a pale yellow solid.Yield: 40.4%,

The chemical industry reduces the impact on the environment during synthesis 3,4,5-Trimethoxyphenylacetonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yanbian University; Bu Gonggaofamingren; (14 pag.)CN108503561; (2018); A;,
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Synthetic Route of 36282-26-5, The chemical industry reduces the impact on the environment during synthesis 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

Step 1 4-Fluoro-2-(6-methyl-pyridin-2-ylamino)-benzonitrile 2-Bromo-4-fluoro-benzonitrile (1.0 g, 5.0 mmol), 6-methyl-pyridin-2-ylamine (540 mg, 5.0 mmol) and Cs2C03 (4.88 g, 15.0 mmol) were dissolved in dioxane (30 mL), then the reaction mixture was de-gassed with nitrogen (purged through the solution for 5 min). Pd2dba3 (229 mg, 0.25 mmol) and Xantphos (289 mg, 0.5 mmol) were added under nitrogen and the mixture heated to 90 C for 4 h. The reaction mixture was cooled, filtered and the filter cake washed with EtOAc (20 mL). The combined filtrates were concentrated under reduced pressure to give a crude residue that was purified by chromatography (silica, 10% to hexane to 15 % EtOAc in hexanes) to give 4-fuoro-2-(6-methyl-pyridin-2-ylamino)-benzonitrile (470 mg, 41 %) as white solid. MS (EI/CI) m/z: 228.2 [M + H].

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-4-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BHAGIRATH, Niala; KENNEDY-SMITH, Joshua; LE, Nam, T.; LUCAS, Matthew, C.; PADILLA, Fernando; SOTH, Michael; WO2014/60371; (2014); 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. 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 4592-94-3

General procedure: To a solution of 0.45 g of 3-(4-bromophenyl)-3-oxopropanenitrile (6a, 2.0 mmol) in 25 mL of ethanol, 0.165 g of benzothiazolylhydrazine (5a, 1.0 mmol) and 0.058 g of propionaldehyde (8a, 1.0 mmol) were added along with 2 drops of conc. HCl. The reaction mixture was heated to reflux for 45 minutes until the formation of a solid product in the reaction mixture. The hot reaction mixture was filtered at the vacuum pump and washed with hot ethanol to afford the pure compound 7a. All other compounds (7b-i) were synthesized according to the procedure mentioned for 7a using heteroarylhydrazines (5a-c), different 3-aryl-3-oxopropanenitriles (6a-d) and aldehydes (8a-d). 1-(Benzo[d]thiazol-2-yl)-4,7-dihydro-4-ethyl-3,6-di(4-bromophenyl)-1H-pyrazolo[3,4-b]pyridine-5-nitrile (7a). Yield 62%; M.p. 240-245 C; IR (KBr, cm-1): 2208 (CN), 3340 (N-H); 1H NMR (400 MHz, CDCl3): delta 0.87-0.90 (t, 3H, CH3, J 6.8 Hz), 1.71-1.89 (m, 2H, CH2), 4.44-4.46 (t, 1H, 4-H, J 4 Hz), 7.38-7.42 (m, 1H, 6?-H), 7.48-7.51 (m, 1H, 5′-H), 7.62-7.69 (m, 6H, Ph-H), 7.72-7.74 (m, 2H, 2??-H), 7.78-7.80 (d, 1H, 7′-H, J 8.0 Hz), 7.86-7.88 (d, 1H, 4′-H, J 8.0 Hz), 9.1 (s, 1H, exchangeable with D2O, 7-H); 13C NMR (75 MHz, CDCl3): delta 8.8, 28.2, 36.6, 84.7, 99.5, 121.7, 121.9, 123.4, 125.1, 125.4, 126.8, 128.7, 129.3, 130.9, 131.5, 132.0, 132.6, 139.9, 148.4, 150.3, 160.7; MS: m/z 615.97 [M+1]+, 617.97 [M+1+2]+, 619.97 [M+1+4]+, (1:2:1); Elemental analysis: Calcd. for C28H19Br2N5S: C, 54.47; H, 3.10; N, 11.34; Found: C, 53.35; H, 2.63; N, 11.12.

The synthetic route of 4592-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Aggarwal, Ranjana; Kumar, Suresh; Singh, Gulshan; Synthetic Communications; vol. 49; 7; (2019); p. 973 – 985;,
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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. 846023-24-3, name is 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

EXAMPLE 15 3-Fluoro-4-methoxyanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide To a suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide (1.00 g, 3.86 mmol) in 200 mL of isopropanol was added 3-fluoro-p-anisidine (0.60 g, 4.25 mmol). This mixture was heated to reflux to give a clear yellow solution. To this solution, triethylorthoformate (1.72 mL, 10.34 mmol) was added dropwise and the reaction mixture was heated at reflux overnight. An additional 2 mL of triethylorthoformate was added and the mixture was heated at reflux overnight. An additional 2 mL of triethylorthoformate was added and the mixture was heated at reflux overnight. The mixture was allowed to cool to room temperature and the white solid was collected by filtration, washed with isopropanol, and dried overnight at ~40 C. under reduced pressure. Purification by suspension in hot ethyl acetate followed by addition of cold hexanes gave 1.08 g (68%) of 3-fluoro-4-methoxyanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide as a white solid, mp 275-276 C.; MS 408.1, 410.1 (M-H)- Analysis for C18H14Cl2FN3O3; Calcd: C, 52.70; H, 3.44; N, 10.24. Found: C, 52.44; H, 3.26; N, 10.14.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 846023-24-3.

Reference:
Patent; Wyeth Holdings Corporation; US2005/43537; (2005); A1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 133541-45-4, name is 4-Bromo-2,5-difluorobenzonitrile, 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 133541-45-4, Recommanded Product: 4-Bromo-2,5-difluorobenzonitrile

EXAMPLE 28 4-Bromo-2-{[(1R)-3-(cyclopropylamino)-1-(phenyl)propyl]oxy}-5-fluorobenzonitrile oxalate Prepared by the method of Example 25 using (R)-alpha-(2-chloroethyl)benzenemethanol and 4-bromo-2,5-difluorobenzonitrile initially before converting into the title compound via in situ conversion to the iodo compound and treatment with cyclopropylamine. The free base was treated with a 50% saturated solution of oxalic acid in ether. The resultant white solid was collected via filtration to yield the title compound (41 mg, 4.2%). MS APCI+ve m/z 390 [(M+H)+]. 1H NMR 400 MHz (d6-DMSO) delta7.96 (d, 1H), 7.49 (d, 1H), 7.45-7.39 (m, 3H), 7.39-7.31 (m, 2H), 5.82-5.74 (m, 1H), 3.16-3.00 (m, 2H), 2.74-2.64 (m, 1H), 2.38-2.25 (m, 1H), 2.24-2.11 (m, 1H), 0.79-0.64 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,5-difluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Cheshire, David; Connolly, Stephen; Cox, David; Hamley, Peter; Mete, Antonio; Pimm, Austen; US2003/158185; (2003); A1;,
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Some common heterocyclic compound, 328-87-0, name is 2-Chloro-5-trifluoromethylbenzonitrile, molecular formula is C8H3ClF3N, 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: 2-Chloro-5-trifluoromethylbenzonitrile

EXAMPLE 7 Preparation of 2-Cyano-alpha,alpha,alpha -trifluoro-p-tolyl-3-ethoxy-4-nitrophenyl ether A solution of potassium hydroxide (2.6 g., 0.04 mole) 87.3% pure and 3-ethoxy-4-nitrophenol (7.3 g., 0.04 mole) in methanol (30 ml) is stripped to dryness under reduce pressure. A residue of potassium 3-ethoxy-4-nitrophenoxide is dissolved in sulfolane (200 g.) and 4-chloro-3-cyano-benzotrifluoride (8.2 g., 0.04 mole) is added. Gas-liquid chromotography shows the reaction to be complete after stirring at 110 C. for 41/2 hours and 135 C. for 21/2hours. The reaction mixture is cooled and poured into deionized water and the precipitate which forms is filtered off and air dried. Recrystallization from isopropanol yields 2-cyano-alpha,alpha,alpha -trifluoro-p-tolyl-3-ethoxy-4-nitrophenyl ether (7.4 g. 53%) m.p. 143-145 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 328-87-0, its application will become more common.

Reference:
Patent; Rohm and Haas Company; US4046798; (1977); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts