Month: August 2021

Electric Literature of 50670-64-9, The chemical industry reduces the impact on the environment during synthesis 50670-64-9, name is 5-Amino-2-methylbenzonitrile, I believe this compound will play a more active role in future production and life.

The 2,4-dicyanobenzyl bromide (melting point 106) can be obtained by bromination of 2,4-dicyanotoluene (melting point 142-143) with bromine in chlorobenzene with ultra-violet irradiation. The 2,4-dicyanotoluene can be formed from 3-cyano-4-methyl-1-aminobenzene by the Sandmeyer reaction.

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, 5-Amino-2-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sandoz Ltd.; US4032558; (1977); A;,
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Reference of 6136-93-2, The chemical industry reduces the impact on the environment during synthesis 6136-93-2, name is 2,2-Diethoxyacetonitrile, I believe this compound will play a more active role in future production and life.

To a stirred solution of 2,2-diethoxyacetonitrile (XIX) (0.33 g, 2.52 mmol) in a vial containing MeOH (2.52 mE) was added MeONa (0.23 mE, 0.25 mmol) dropwise. The reaction was stirred at 22 C. for 20 h. HOAc was added (14.4 tE, 0.25 mmol) (checked that the pH is 7-8 using pH strips) followed by (4-bromo-3-methyl-phenyl)methan- amine (XXV) (0.5 g, 2.52 mmol). The mixture was stirred at 40 C. for 40 h. The solvent was removed under vacuum. Sulthric Acid (4.09 mE, 75.49 mmol) was then added and stirred at 40 C. for 16 h. NH4OH (33.4 mE, 78 mmol) was added at 0 C. The reaction was filtered through Celite and purified by C18 silica gel (240 g) [0-30% H20/MeCN (0.1% Formic acid)] to produce a 1:1 mixture (by NMR) of 6-bromo-7-methylisoquinolin-3-amine (XXVI) and6-bromo-5-methylisoquinolin-3-amine (XXVII) (378 mg,1.59 mmol, 63.4% yield). ?H NMR (499 MHz, DMSO-d5)0 ppm 2.40 (3H, s), 2.52 (3H, s), 5.96 (2H, s), 6.12 (1H, s),6.54 (1H, s), 6.71 (1H, s), 7.27 (1H, d, J=8.78 Hz), 7.58 (1H, d, J=8.78 Hz), 7.73 (1H, s), 7.86 (1H, s), 8.74 (1H, s), 8.79 (1H, s); ESIMS found for C,0H9BrN2 mlz 237.0 (79BrM+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, 2,2-Diethoxyacetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Mak, Chi Ching; Hofilena, Brian Joseph; Mittapalli, Gopi Kumar; Eastman, Brian Walter; Cao, Jianguo; Bollu, Venkataiah; Chiruta, Chandramouli; (149 pag.)US2019/125740; (2019); A1;,
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Related Products of 330792-69-3, These common heterocyclic compound, 330792-69-3, name is 2-(Methoxy(4-phenoxyphenyl)methylene)malononitrile, 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.

1,1-Dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene (22.5 g) and 1,1-dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene oil (15g) are treated with a solution of hydrazine hydrate (18 mL) in ethanol (25 mL) and heated on the steambath for 1 hour. Ethanol (15 mL) is added followed by water (10 mL). The precipitated solid is collected and washed with ethanol:water (4:1) and then dried in air to give 3-amino-4-cyano-5-(4-phenoxyphenyl)pyrazole as a pale orange solid.

The synthetic route of 330792-69-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmacyclics, Inc.; Buggy, Joseph J.; Chang, Betty Y.; US2013/178483; (2013); A1;,
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Some common heterocyclic compound, 330793-38-9, name is 4-Bromo-2-methoxybenzonitrile, molecular formula is C8H6BrNO, 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. Product Details of 330793-38-9

b 4-Bromo-2-methoxybenzoic acid 4-Bromo-2-methoxybenzonitrile (7.35 g, 35 mmol) was dissolved in dioxane (400 mL). Sodium hydroxide (2.0 N, 200 mL) was added and the suspension was heated at 100° C. for 16hours. Organic solvent was removed under reduced pressure and the aqueous mixture was filtered and washed with water. The filtrate was neutralized with hydrochloric acid (5.0N) to pH 1. The solid was collected by filtration to give 4-bromo-2-methoxybenzoic acid (3 g, 37percent). 1H NMR (DMSO-d6) delta 3.84(s, 3H), 7.21 (d, J=8.25 Hz, 1H), 7.33 (s, 1H), 7.58 (d, J=8.23 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 330793-38-9, its application will become more common.

Reference:
Patent; Abbott Laboratories; US2002/156081; (2002); A1;,
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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. 194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Fluoro-2-(trifluoromethyl)benzonitrile

General procedure: Sixty per cent NaH in oil was washed with hexane and then added to a stirred solution of phenothiazine 5 or phenoxazine 6 derivative (10.0mmol) in dry THF (15mL) under a nitrogen atmosphere at room temperature. After stirring for 30min, 4-fluoro-2-(fluoromethyl)-benzonitrile 7 was added. (0007) The reaction mixture was quenched with water (30mL). The organic phase was separated, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue obtained was purified by column chromatography using a mixture of hexane/ethyl acetate (3:1) as eluent.

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 194853-86-6.

Reference:
Article; Baraket, Faiza; Pedras, Bruno; Torres, Erica; Brites, Maria Joao; Dammak, Mohamed; Berberan-Santos, Mario N.; Dyes and Pigments; vol. 175; (2020);,
Nitrile – Wikipedia,
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Electric Literature of 64248-62-0, 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. 64248-62-0, name is 3,4-Difluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of terf-butyl-(S)-3-hydroxypyrrolidine-l-carboxylate (4.44 g, 23.7 mmol) in N,N- dimethylformamide (40 mL), sodium hydride (1.72 g, 43.1 mmol) was added under nitrogen atmosphere at 0 C and stirred for 30 min. To the resulting reaction mixture, 3,4-difluorobenzonitrile (3 g, 21.6 mmol) in /V, /V-di methylformam ide (10 mL) was added slowly at 0 C and stirred at 25 C for 2 h. The reaction mixture was quenched with ammonium chloride solution and diluted with ethyl acetate (100 mL). The dichloromethane layer was collected and washed twice with water (80 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by flash column chromatography on silica gel by eluent 50% ethyl acetate in hexane to obtain tert- butyl (S)-3-(4-cyano-2-fluorophenoxy)pyrrolidine-l-carboxylate (5.3 g, 17.3 mmol, 80% yield).

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

Reference:
Patent; PI INDUSTRIES LTD.; BHUJADE, Paras Raybhan; NAIK, Maruti N; PAWAR, Rajesh; TRIVEDI, Pooja; DENGALE, Rohit Arvind; KULKARNI, Shantanu Ganesh; TEMBHARE, Nitin Ramesh; AUTKAR, Santosh Shridhar; GARG, Ruchi; VENKATESHA, Hagalavadi M; KLAUSENER, Alexander G.M.; (172 pag.)WO2020/70610; (2020); A1;,
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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. 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Fluoro-5-nitrobenzonitrile

General procedure: General procedure: 3-Hydroxy oxetane (370 mg, 5 mmol, 2 equiv) in THF (15 ml) under argon gas, was cooled to 0 C. Potassium tert-butoxide (617 mg, 5.5 mmol, 2.2 equiv) was added in one portion, and the reaction mixture was stirred for 20 minutes at 0 C. Then 2-fluoro-5-nitrobenzonitrile (415 mg, 2.5 mmol, 1 equiv) was added in one portion, and the reaction mixture was stirred for 10 minutes at 0 C and allowed to warm up to ambient temperature over 1 hour. The reaction mixture was concentrated, and the residue was taken in DCM and water. The layers were separated, and the organic layer was washed with water (x2), dried over Na2S04, filtered, and concentrated to provide 5-nitro-2-(oxetan- 3-yloxy)benzonitrile (495 mg, 90%) as a brown-yellow solid that was used without further purification. [00576] 1H NMR (300 MHz; 6-DMSO) delta 8.74-8.75 (m, 1H), 8.42-8.47 (m, 1H), 7.09- 7.12 (dd, 1H, J = 0.9Hz, J = 9.3Hz), 5.56-5.63 (m, 1H), 4.96-5.00 (m, 2H), 4.59-4.63 (m, 2H); m/z = 221 (M+H)+.

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 17417-09-3.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; SINGH, Rajinder; DUNCTON, Matthew; ZHANG, Jing; ALVAREZ, Salvador; TSO, Kin; HOLLAND, Sacha; YEN, Rose; KOLLURI, Rao; HECKRODT, Thilo; CHEN, Yan; MASUDA, Esteban; LI, Hui; PAYAN, Donald G.; KELLEY, Ryan; WO2013/152198; (2013); A1;,
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Application of 7357-70-2, 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. 7357-70-2, name is 2-Cyanothioacetamide belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 12A (S)-2-Amino-4-{4-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]phenyl}-6-mercaptopyridine-3,5-dicarbonitrile 1.52 g (6.43 mmol) of the compound from Example 11A, 1.29 g (12.9 mmol) of cyanothioacetamide and 1.3 g (12.9 mmol) of 4-methylmorpholine are dissolved in 15 ml of ethanol, and the mixture is stirred under reflux for 3 h. The mixture is then stirred at RT for 18 h. The reaction solution is concentrated using a rotary evaporator, and the residue is chromatographed on silica gel 60 (mobile phase: dichloromethane/ethanol 10:1). Yield: 1.06 g (43% of theory) LC-MS (Method 3): Rt=1.75 min; MS (ESIpos): m/z=383 [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-Cyanothioacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer HealthCare AG; US2008/269300; (2008); A1;,
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Synthetic Route of 1897-52-5,Some common heterocyclic compound, 1897-52-5, name is 2,6-Difluorobenzonitrile, molecular formula is C7H3F2N, 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.

4-(2-Cyano-3-fluorophenyl)piperazine-l-carboxylic acid tert-butyl ester. In a round bottom flask, sodium hydride (60%) (2.40 g; 60 mmol) was suspended in DMF (25 mL) and cooled in an ice water bath under nitrogen. 1-Boc- Piperazine (9.53 g; 50.6 mmol) was added in small portions to the reaction mixture at 0 C over 30 minutes. The mixture was allowed to stir at room temperature for 3 hours and the recooled to 0 C. 2,6-Difluorobenzonitrile (8.57 g; 60 mmol) was added to the reaction mixture in DMF (10 mL) over 45 minutes. The mixture was stirred at room temperature for 16 hours. The reaction mixture was poured in ice water (250 mL) and stirred. The solid was collected by vacuum filtration and washed with water. And then dried under vacuum to yield the title compound (11.65 g; 75% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Difluorobenzonitrile, its application will become more common.

Reference:
Patent; deCODE Chemistry, Inc.; WO2008/16973; (2008); A1;,
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24973-49-7, name is [1,1′-Biphenyl]-2-carbonitrile, 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. category: nitriles-buliding-blocks

General procedure: A stirring suspension of lithium aluminum hydride (1.1equiv) in anhydrous THF was treated dropwise under N2 with a solution of aluminum chloride (0.9equiv) in THF. The reaction mixture was maintained at room temperature during the addition by means of a water bath. After addition was complete, the reaction mixture was stirred vigorously for 20min and then cooled to 0C before adding dropwise a solution of biphenyl-2-carbonitrile 4 (1.0equiv) in THF. After complete addition, stirring was continued for 2h and the reaction was quenched by slowly adding methanol followed by water. The mixture was concentrated under reduced pressure, and the residue was extracted with 1N HCl. The aqueous phase were combined, washed with EtOAc and neutralized by addition of 10N NaOH. The mixture was extracted with CH2Cl2, the organic phase was combined, washed with water, dried over Na2SO4 and evaporated under reduced pressure. The residue was filtered through a pad of silica gel, and the filtrate was evaporated and dried to give the product 5 in 60-75% yields. 4.3.1 Biphenyl-2-ylmethanamine (5-1) The reaction of lithium aluminum hydride (2.15 ml, 2.15 mmol) in anhydrous THF, aluminum chloride (234 mg, 1.76 mmol), and biphenyl-2-carbonitrile (350 mg, 1.95 mmol) in THF (5 ml) gave the title compound 5-1 (256 mg, 1.40 mmol, 72% yield). 1H NMR (400 MHz, CDCl3) delta 7.46 (d, J = 7.5 Hz, 1H), 7.41-7.40 (m, 2H), 7.37-7.32 (m, 3H), 7.30 (td, J = 7.5, 1.3 Hz, 1H), 7.24 (dd, J = 8.1, 2.1 Hz, 1H), 3.81 (s, 2H), 1.34 (s, 2H).

The synthetic route of 24973-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kim, Youngjae; Tae, Jinsung; Lee, Kangho; Rhim, Hyewhon; Choo, Il Han; Cho, Heeyeong; Park, Woo-Kyu; Keum, Gyochang; Choo, Hyunah; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4587 – 4596;,
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