Tag: M.W=100-200

Reference of 214759-66-7,Some common heterocyclic compound, 214759-66-7, name is Methyl 3-chloro-4-cyanobenzoate, molecular formula is C9H6ClNO2, 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 4) (0897) A mixture of the compound obtained in Step 3 (500 mg, 2.56 mmol), 4 mol/L aqueous lithium hydroxide solution (10 mL, 40.00 mmol) and THF (10 mL) was stirred at room temperature for 3 hr. The reaction mixture was washed with toluene, acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give 3-chloro-4-cyanobenzoic acid as a colorless solid (quantitative). MS (API) :180 (M-H)

The synthetic route of 214759-66-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; FUKASE, Yoshiyuki; SATO, Ayumu; KOUNO, Mitsunori; TOMATA, Yoshihide; OCHIDA, Atsuko; YONEMORI, Kazuko; ODA, Tsuneo; IMADA, Takashi; YUKAWA, Tomoya; (238 pag.)EP2975031; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 4640-66-8,Some common heterocyclic compound, 4640-66-8, name is 4-Chlorophenacylcyanide, molecular formula is C9H6ClNO, 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: Benzoyl acetonitrile (1, 0.5 mmol), cyclic 2-diazo-1,3-dicarbonyl compound (2, 1.25 mmol), [RhCp*Cl2]2 (0.025 mmol), CsOAc (0.25 mmol), Cu(OAc)2*H2O (1.0 mmol) and DCE (2 mL) were sequentially charged into a reaction tube. The tube was then sealed and the mixture was stirred at 80 C. Upon completion, it was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (10 mL * 3). The combined organic phase was dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleum ether/ethyl acetate (5:1) as eluent to afford 3.

The synthetic route of 4640-66-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Beibei; Li, Bin; Guo, Chenhao; Zhang, Xinying; Fan, Xuesen; Tetrahedron Letters; vol. 59; 32; (2018); p. 3094 – 3099;,
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

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. 626-17-5, name is 1,3-Dicyanobenzene, A new synthetic method of this compound is introduced below., Product Details of 626-17-5

EXAMPLE 1 Hydrogenation of Isophthalonitrile Into a 100-ml autoclave, were charged 3.2 g of isophthalonitrile, 10.4 g of mesitylene, 10.0 g of liquid ammonia and 2.0 g of Pd-alumina pellets (manufactured by N.E. Chemcat Corporation; Pd content = 5% by weight), and the inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of isophthalonitrile was 95.7 mol%, the yield of 3-cyanobenzylamine was 87.3 mol% and the yield of m-xylynenediamine was 7.7 mol%. The reaction solution separated from the catalyst was charged into a 100-ml autoclave together with 10.0 g of liquid ammonia and 2.0 g of Ni-diatomaceous earth pellets (manufactured by Nikki Chemical Co., Ltd.; Ni supported amount = 46% by weight). The inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of isophthalonitrile was 100 mol%, the yield of 3-cyanobenzylamine was 0.2 mol% and the yield of m-xylynenediamine was 89.4 mol% EXAMPLE 4 Hydrogenation of Isophthalonitrile Into a 100-ml autoclave, were charged 3.2 g of isophthalonitrile, 10.4 g of mesitylene, 10.0 g of liquid ammonia and 2.0 g of Pd-alumina pellets (manufactured by N.E. Chemcat Corporation; Pd content = 5% by weight), and the inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of isophthalonitrile was 95.7 mol%, the yield of 3-cyanobenzylamine was 87.3 mol% and the yield of m-xylynenediamine was 7.7 mol%. The reaction solution separated from the catalyst was charged into a 100-ml autoclave together with 10.0 g of liquid ammonia and 2.0 g of the catalyst A. The inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of isophthalonitrile was 100 mol%, the yield of 3-cyanobenzylamine was 0.0 mol% and the yield of m-xylynenediamine was 91.1 mol%.

The synthetic route of 626-17-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MITSUBISHI GAS CHEMICAL COMPANY, INC.; EP1449825; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 935-02-4, A common heterocyclic compound, 935-02-4, name is 3-Phenylpropiolonitrile, molecular formula is C9H5N, 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.

Dissolve 0.5 mmol of acetylene nitrile (1) in 2 mL of acetic acid,After addition of 0.75 mmol (62.3 mg) of lithium bromide, the reaction mixture was obtained;The reaction mixture was heated to 110C and stirred for 12 hours to give the first product;After the first product was cooled, 10 mL of water was added thereto to obtain a second product.Ethyl acetate is added to the second product and extracted twiceEach time 10 mL was added, the first organic phase product was obtained after extraction with the ethyl acetate;After washing the first organic phase product with brine for 1 time,After drying the first organic phase product over anhydrous sodium sulfate for 2 hours, a second organic phase product is obtained.The second organic phase product is distilled under reduced pressure to remove ethyl acetate to obtain a third organic phase product;Silica gel chromatography column (silicon gel particle size 200-300 mesh, eluent is a mixed solvent of petroleum ether and ethyl acetate,The volume ratio of the petroleum ether and the ethyl acetate is 200:1) to separate the third organic phase product,The product (3) is obtained,The product (3) is 3-bromo-3-aryl acrylonitrile, and the chemical reaction formula of acetylene nitrile and lithium bromide is as follows:

The synthetic route of 935-02-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huazhong Agricultural University; Shi Wei; Guan Zhipeng; Tang Jiahao; Chen Hao; (13 pag.)CN107814752; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, 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. Formula: C7H3ClFN

To an ice-cooled mixture of 23 (0.100 g, 0.485 mmol) and DMF (1.0 mL) was added NaH (60% in mineral oil, 0.023 g, 0.582 mmol), and the mixture was stirred at 0 C for 30 min. To the mixture was added 2-chloro-4-fluorobenzonitrile (0.151 g, 0.970 mmol), and the mixture was stirred at 0 C for 1 h. The mixture was mixed with saturated aqueous solution of NaHCO3 and extracted twice with EtOAc. The organic layers were combined, washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc) to afford 25 (0.088 g, 53%) as a white solid, mp 118-119 C. 1H NMR (300 MHz, CDCl3) delta: 2.13 (3H, s), 2.32 (3H, s), 6.82-6.91 (2H, m), 6.96-7.05 (2H, m), 7.55 (1 H, dd, J = 8.7 and 1.9 Hz), 7.72-7.81 (2H, m). Anal. Calcd for C18H13ClFN3O: C, 63.26; H, 3.83; N, 12.29. Found: C, 63.22; H, 3.78; N, 12.35.

The synthetic route of 60702-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yamamoto, Satoshi; Tomita, Naoki; Suzuki, Yuri; Suzaki, Tomohiko; Kaku, Tomohiro; Hara, Takahito; Yamaoka, Masuo; Kanzaki, Naoyuki; Hasuoka, Atsushi; Baba, Atsuo; Ito, Mitsuhiro; Bioorganic and Medicinal Chemistry; vol. 20; 7; (2012); p. 2338 – 2352;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 1187-42-4,Some common heterocyclic compound, 1187-42-4, name is Diaminomaleonitrile, molecular formula is C4H4N4, 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.

The compound J (0.70 g, 1.56 mmol), diaminomaleonitrile (0.20 g, 1.85 mmol), 40 mL of ethanol, 20 mL of THF, and 0.24 mL of a 12M hydrochloric acid were charged in a three-necked flask having a capacity of 300 mL, and the mixture was stirred while heating at 40 C. for 24 hours. Water was added to the resultant solution, the resultant mixture was subjected to extraction with chloroform, and then the resultant extract was dried by adding sodium sulfate thereto. Sodium sulfate hydrate was removed by conducting filtration, and the solvent was distilled off from the filtrate using an evaporator. The resultant solid was purified by silica gel column chromatography (developing solvent: toluene) to obtain a yellow solid (yield amount: 0.40 g, yield: 49%). Chemical shift values (delta) of the compound measured by 1H NMR (400 MHz, CDCl3) were as follows: delta 9.32 (d, J=8.4 Hz, 1H), 9.25 (dd, J=10.8, 2.8 Hz, 1H), 8.94 (d, J=2.0 Hz, 1H), 8.80 (d, J=8.8 Hz, 1H), 8.20-8.16 (m, 3H), 8.07 (dd, J=8.8, 2.4 Hz, 2H), 8.01 (td, J=8.8, 1.6 Hz, 1H), 7.89 (td, J=7.2, 1.2 Hz, 1H), 7.81 (dd, J=8.4, 2.0 Hz, 2H), 7.55-7.52 (m, 2H), 7.47 (dd, J=7.2, 1.2 Hz, 2H), 7.36-7.31 (m, 2H). It was confirmed by 1H NMR measurement that the obtained compound was a compound 4 (Cz-CNBQx).

The synthetic route of 1187-42-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KYUSHU UNIVERSITY, NATIONAL UNIVERSITY CORPORATION; Nippon Soda Co., Ltd.; YASUDA, Takuma; FURUE, Ryuhei; ISHIHARA, Hiroyuki; FUKUSHIMA, Yukio; (61 pag.)US2019/330162; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 915394-29-5, 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. 915394-29-5, name is 2-(3-Aminophenyl)-2-methylpropanenitrile, This compound has unique chemical properties. The synthetic route is as follows.

Example 25; l-[3-(Cyano-dimethyl-methyl)-phenyl]- 3-{4-[2-(3-hydroxy-propylamino)- pyrimidin-4-yloxy]-phenyl}-urea196 mg (1.21 mmol) l.l’-Carbonyl-diimidazol (CDI) were given to a solution of 176 mg (l.lOmmol) 3-(cyano-dimethyl-methyl)-phenylamine in 4.0 ml dichloro- methane and stirred for 12 h. A solution of 286 mg (1.10 mmol) 3-[4-(4-Amino- phenoxy)-pyrimidin-2-ylamino]-propan-l-ol in 6 ml dichloromethane was added within 30 min. and the mixture stirred for 12 h at r.t. The reaction mixture was evaporated and the residue was purified by chromatography on silica gel ( dichloromethane/ ethanol 96:4). The obtained material was leached with ether, filtered and dried. Yield 74 mg (15%) of the title compound. MS: 447.38 (ESI+), 445.32 (ESI-).eta-NMR(400Hz, [DJDMSO): delta = 1.59(br, 2H, CH2-CH2-CH2), 1.68(s, 6H, CH3), 3.2(br, 2H, CH2-NH), 3.39(br, 2H, CH2-OH), 4.38(br, IH, OH), 6.06(br, IH, 5-H- pyrimidine), 7.05(br, IH, CH2NH), 7.10(m, 3H, 3-H/5-H -Ar-NH, 4-H-Ar-C-CN),7.34(t, IH, 5-H-Ar-C-CN), 7.42(d, IH, 6-H-Ar-C-CN), 7.48(d, 2H, 2-H/6-H-Ar- NH), 7.66(s, IH, 2-H-Ar-C-CN), 8.12(d, IH, 6-H-pyrimidine), 8.72(s, IH, urea- NH), 8.84(s, IH, urea-NH).

The chemical industry reduces the impact on the environment during synthesis 2-(3-Aminophenyl)-2-methylpropanenitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/77548; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 243128-37-2, 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. 243128-37-2, name is 4-Fluoro-3-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 5-chloro-2,lambda/-dimethylbenzamide (5.0 g, 27.2 mmol) in THF (28 ml_) was cooled to -78 C and a solution of 2M lithium diisopropylamide in THF (40.8 ml_, 82 mmol) diluted with THF (68 mL) added. 4-Fluoro-3-methoxybenzonitrile (4.12 g, 27.2 mmol) in THF (28 ml_) was added and the mixture stirred at -78 C for 2.5 h. Sat. NH4CI (aq.) was added and the mixture extracted with EtOAc (2 X 50 mL). A precipitate formed in the aqueous which was collected by filtration to afford 7-chloro-3-(4-fluoro-3-methoxyphenyl)-2H-isoquinolin-1- one (3.74 g, 12.3 mmol, 45%).

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

Reference:
Patent; N.V. ORGANON; WO2008/33764; (2008); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 117482-84-5, 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 117482-84-5 as follows.

Anhydrous p-toluene sulfonic acid (10 g, 52.57 mmol) was melted at 120 C and 3-amino-4-methoxy benzoic acid methyl ester (3.88 g, 21.44 mmol) obtained in step 1 of Preparation Example 1 and 3-chloro-4-fluorobenzonitrile (5.0 g, 32.14 mol) were added thereto and stirred at 160 C for 8 hours. The resulting solution was cooled to room temperature and the reaction was stopped by adding NaHCO3 thereto. The resulting mixture was extracted with ethyl acetate, the extract was dried over MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (3.24 g, 9.62 mmol) in a yield of 45 %. 1H NMR (CDCl3): delta 7.96-7.95 (1H, m), 7.76-7.73 (2H, m), 7.60 (1H, bs), 7.17-7.11 (1H, m), 6.93 (1H, d), 3.85 (3H, s), 3.84 (3H, d) MW: 336

According to the analysis of related databases, 117482-84-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CRYSTALGENOMICS, INC.; YUYU INC.; WO2004/65370; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts