Month: November 2020

A common heterocyclic compound, 151-18-8, name is 3-Aminopropanenitrile, molecular formula is C3H6N2, 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. 151-18-8.

EXAMPLE 2 To 59.5 parts of sodium methylate is added 300 parts by volume of tetrahydrofuran, and the mixture is cooled at -5C and then to the mixture is added dropwise 70 parts of beta-aminopropionitrile. Into the mixture is introduced carbon monoxide at 50 kg/cm2 G at 70C for 4 hours to allow the reaction to take place. After completion of the reaction, the solvent is removed and the crystals are recovered by filtration and washed with tetrahydrofuran, whereby 116 parts of alpha-sodioformylbeta-formylaminopropionitrile is obtained. Melting point: 178C(decomp.) Purity: 79 %. Yield: 62 %.

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

Reference:
Patent; Takeda Chemical Industries, Ltd.; US3954756; (1976); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 3556-60-3, name is 3-Methoxy-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., 3556-60-3

A mixture of 3-methoxy-4-methylbenzonitrile (3.5 g, 24 mmol), NBS (4.4 g, 25 mmol), and AIBN (0.39 g, 2.4 mmol) in benzene (240 mL) under nitrogen was heated at 85 C for 18 h, then cooled and concentrated. The residue was purified by silica gel chromatography (hexanes initially, grading to 50% EtOAc in hexanes) to give the title compound. MS: mlz = 226.0 [M+l]+.

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; MERCK SHARP & DOHME CORP.; CROWLEY, Brendan; FRALEY, Mark; POTTEIGER, Craig; LIM, John; SHERER, Ed; YU, Younong; MITCHELL, Helen; BIFTU, Tesfaye; NAIR, Anilkumar; WANG, Cheng; YANG, De-Yi; ZHU, Cheng; KAR, Nam Fung; HUANG, Xianhai; CHEN, Lei; ZHOU, Wei; PARK, Min, K.; CAI, Jiaqiang; WO2015/161014; (2015); A1;,
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127946-77-4, 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. 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, A new synthetic method of this compound is introduced below.

To a solution of Compound 42 (301 mg, 0.854 mmol) in dimethylformamide (4 ml) were successively added 1-aminocyclopropanecarbonitrile hydrochloride (304 mg, 2.56 mmol), triethylamine (0.8 mL, 6.7 mmol) and HATU (812 mg, 2.14 mmol) under nitrogen atmosphere, then the reaction mixture was stirred at room temperature for 2 hours. To the reaction solution was added 10% aqueous sodium bicarbonate solution, then the reaction solution was extracted with ethyl acetate. The extraction was washed with brine, then dried over sodium sulfate. The solvent was removed under reduced pressure. The obtained residue was purified by column chromatography to give Compound (I-3-1) (220 mg, 62%) as a white solid.Compound (I-3-1); 1H-NMR (DMSO-d6) delta: 1.14 (dd, J=8.36, 5.32 Hz, 2H), 1.49 (dd, J=8.11, 5.58 Hz, 2H), 3.91 (s, 2H), 4.97 (s, 2H), 7.37-7.40 (m, 1H), 7.93 (td, J=7.73, 1.69 Hz, 1H), 8.07 (dd, J=8.62, 2.03 Hz, 2H), 8.27 (dd, J=8.62, 2.03 Hz, 1H), 8.70 (d, J=4.56 Hz, 1H), 8.85 (d, J=1.52 Hz, 1H), 9.23 (s, 1H).

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; Shionogi & Co., Ltd.; US2012/253040; (2012); A1;,
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151-18-8, Adding a certain compound to certain chemical reactions, such as: 151-18-8, name is 3-Aminopropanenitrile, 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 151-18-8.

To a solution of 4-(((6-methylpyridin-2-yl)carbonyl)amino)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylic acid obtained in Reference Example 47 (0.66 g, 2.0 mmol) and 3-aminopropionitrile (0.18 mL, 2.4 mmol) in DMF (15 mL), WSC (0.41 g, 2.4 mmol) and HOBt (0.32 g, 2.4 mmol) were added, and the mixture was stirred at room temperature for 6 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate 1:1) to give the title compound (0.75 g, yield 92%) as crystals. melting point 186-187C. 1H-NMR (CDCl3) :delta 1.60-1.80(3H, m), 2.00-2.15 (2H, m), 2.15-2.30 (1H, m), 2.70(3H, s), 2.76(2H, t, J=6.6 Hz), 3.75(2H, t, J=6.6 Hz), 3.65-3.80 (1H, m), 4.00-4.55 (1H, m), 5.36 (1H, d, J=7.2 Hz), 7.20-7.30 (1H, m), 7.32 (1H, d, J=7.2 Hz), 7.75 (1H, t, J=7.7 Hz), 8.03 (1H, d, J=6.9 Hz), 8.58 (1H, s), 11.53 (1H, s).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1847531; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

94087-40-8,Some common heterocyclic compound, 94087-40-8, name is 3-Chloro-2-fluorobenzonitrile, molecular formula is C7H3ClFN, 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.

Intermediate 52: (3-chloro-2-(piperidin- -yl)phenyl)methanamine Step 1: To a solution of 3-chloro-2-fluorobenzonitrile (CAS 94087-40-8) (2.3 mmol) and piperidine (2.8 mmol) in 10 mL of DMF was added K2CO3 (4.6 mmol). The reaction was stirred at RT for 12 h, then the reaction mixture was extracted with water and EtOAc, washed with brine, dried over Na2S04, then concentrated in vacuo to provide 3-chloro-2-(piperidin-l- yl)benzonitrile as a yellow solid which was used in Step 2 without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-2-fluorobenzonitrile, its application will become more common.

Reference:
Patent; KAROS PHARMACEUTICALS, INC.; DE LOMBAERT, Stephane; GOLDBERG, Daniel R.; BRAMELD, Kenneth Albert; SJOGREN, Eric Brian; WO2015/89137; (2015); A1;,
Nitrile – Wikipedia,
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332-25-2, 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. 332-25-2, name is 4-(Trifluoromethoxy)benzonitrile, A new synthetic method of this compound is introduced below.

Step A: Anhydrous CeCl3 (0.84 g, 3.4 mmol) was stirred in dry THF (10 mL), at room temperature, under a N2 atmosphere for 2 h. Then, the solution was cooled at -78 ¡ãC, followed by dropwise addition of MeLi (2.2 mL, 3.4 mmol, 1.6 M), and allowed to stir for 30 min at -78 ¡ãC. Then, a solution of 4-methoxybenzonitrile (0.15 g, 1.1 mmol) in dry THF (5 mL) was added dropwise to the above solution. The crude reaction was stirred at room temperature overnight, quenched by adding 1.5 mL of concentrated NH4OH, and allowed to stir for 1 h at room temperature. The organic layer was filtered, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was used for next reaction without further purification.

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; Gallardo-Macias, Ricardo; Kumar, Pradeep; Jaskowski, Mark; Richmann, Todd; Shrestha, Riju; Russo, Riccardo; Singleton, Eric; Zimmerman, Matthew D.; Ho, Hsin Pin; Dartois, Veronique; Connell, Nancy; Alland, David; Freundlich, Joel S.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 4; (2019); p. 601 – 606;,
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6136-68-1, 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. 6136-68-1, name is 3-Acetylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred mixture of SeO2 (20 mmol, 2.2 g) in dioxane (20 mL) was added water (2 mL) and heated toreflux until SeO2 was dissolved. Compound 1a (10 mmol, 1.45 g) was added and the mixture wasstirred at reflux overnight. After completion, the mixture was filtered through a pad of celite. Thefiltrate was concentrated in vacuo. Compound 3-(2-oxoacetyl)benzonitrile was obtained and useddirectly in next step without further purification. To a suspension of alpha-aminoacetamide hydrochloride(1.5 g, 14 mmol) in MeOH (12.5 mL)-water (3.1 mL) was added 12.5 M aqueous NaOH (1.65 mL, 20mmol) solution at -30 C, and then a solution of NaOH (543 mg, 14 mmol) in MeOH (6.1 mL) wasadded to the mixture. A solution of 3-(2-oxoacetyl)benzonitrile in MeOH (11.1 mL) was added to themixture at -20C, and then the resulting suspension was stirred for 2h at same temperature, and thestirring continued for 1 h at room temperature. After cooling with ice water, the mixture was acidifiedwith AcOH. Collection of the resulting precipitates by filtration gave 2a (52%) as a red solid:

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; Zhang, Niu-niu; An, Bai-jiao; Zhou, Yan; Li, Xing-shu; Yan, Ming; Molecules; vol. 24; 6; (2019);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

25808-30-4, 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. 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, A new synthetic method of this compound is introduced below.

EXAMPLE 8 3-Amino-1,4,5-trimethyl-1H-pyrrole-2-carbonitrile 10.3 ml (0.74 mole) of triethylamine, 7.2 g (0.74 mole) of 3-cyanobutan-2-one and 0.5 g of p-toluenesulfonic acid are successively added to a suspension of 7.8 g (0.74 mole) of N-methylaminoacetonitrile hydrochloride in 70 ml of chloroform, and the mixture is boiled for 5 hours, using a water separator. After it has been boiled, the mixture is washed twice with 10 ml of water each time and dried over sodium sulfate; the solvent is then stripped off in vacuo. In order to remove all of the chloroform, the residue is twice taken up in 100 ml (each time) of dry ethanol, and the mixture concentrated each time in vacuo. The resulting oil is warmed (bath temperature of 50¡ã C.) in 100 ml of 1 N sodium ethylate/ethanol for 2 hours; some of the ethanol is removed. The mixture is then taken up in 100 ml of water and extracted several times with methylene chloride. After being dried over sodium sulfate and concentrated on a rotary evaporator, the extracts yield a solid residue, which is recrystallized from diisopropyl ether.

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; BYK Gulden Lomberg Chemische Fabrik Gesellschaft mit beschrankter Haftung; US4363816; (1982); A;,
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Nitriles – Chemistry LibreTexts

4110-35-4, 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. 4110-35-4, name is 3,5-Dinitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1.1.62: 5-(aminomethyl)-Nl, N l,N3,N3-tetramethylbenzene- 1,3 -diamine; 20% Pd(OH)2 (0.13 g) was added to a stirred suspension of 3,5-dinitrobenzonitrile (0.50 g, 2.59 mmol, 1 eq, Aldrich) in 10 ml EtOH. A H2 balloon was added. After stirring over the weekend the mixture was filtered through Celite. The filter cake was rinsed with EtOH (x3). The organics were removed in vacuo. The residue was stirred in CHCl3 and the resulting mixture was filtered (x3). The CHCl3 fractions were combined, and the solvent was removed in vacuo to yield crude 3,5-diaminobenzonitrile.

The synthetic route of 4110-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COMENTIS, INC.; PURDUE RESEARCH FOUNDATION; WO2009/42694; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, 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. 1835-65-0

General procedure: In the synthesis of Example 1 (1) The compound (4-1), except that a beta-naphthol(compound (a-1)), a 2,4,6-trimethyl-thiophenol (Compound (a-2)) It is to obtain a compound (4-2) in the same manner (yield: 68.1percent).

Statistics shows that 1835-65-0 is playing an increasingly important role. we look forward to future research findings about 3,4,5,6-Tetrafluorophthalonitrile.

Reference:
Patent; Yamada Kagaku Kogyo Corporation; Satoshi, Hayashi; Yosuke, Manabe; (47 pag.)KR2016/40133; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts