Month: August 2021

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. 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, A new synthetic method of this compound is introduced below., Safety of 4-(Hydroxymethyl)benzonitrile

General procedure: To 16 mL of acetonitrile/water (1:1 v/v) mixture was added 0.5-1.2 mmol of the starting compound. The contents were heated at reflux with introduction of oxone (cf. entries for each case) incrementally over the entire duration of the reaction. For secondary benzyl halides, the reactions were run at room temperature. The progress of the reaction in each case was monitored by TLC analysis. After completion of the reaction, the reaction mixture was cooled to room temperature and the organic matter was extracted with ethyl acetate. The combined organic extract was dried over anhyd Na2SO4 and concentrated in vacuo. Short pad silica gel column chromatography of the residue led to isolation of the pure product.

The synthetic route of 874-89-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Parida, Keshaba Nanda; Jhulki, Samik; Mandal, Susovan; Moorthy, Jarugu Narasimha; Tetrahedron; vol. 68; 47; (2012); p. 9763 – 9768,6;; ; Article; Parida, Keshaba Nanda; Jhulki, Samik; Mandal, Susovan; Moorthy, Jarugu Narasimha; Tetrahedron; vol. 68; 47; (2012); p. 9763 – 9768;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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.

A mixture of t-butylhydrazine hydrochloride (4.67 g, 53 mmol) and triethylamine (5.35 g, 53 mmol) in anhydrous ethanol (250 ml) was stirred and ethoxymethylene malononitrile (6.47 g, 53 mmol) was slowly added in portions. The mixture was heated at reflux for 3 hr. The solvent was removed in vacuo and the product was crystallized from ethyl acetate – hexane followed by ether to afford 5-amino-l-tert-butyl-lH-pyrazole-4-carbonitrile as light pale brown crystals (5.6 g, 34.1 mmol); LC/MS, API-ES, Neg, (M-H)”, 163.0.

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, Ethoxymethylenemalononitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FOLDRX PHARMACEUTICALS, INC.; WO2009/62118; (2009); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 1093951-76-8,Some common heterocyclic compound, 1093951-76-8, name is 2-Amino-3-bromo-4-fluorobenzonitrile, molecular formula is C7H4BrFN2, 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: 9-Amino-4-X-5-bromo-2-(alkyl)-2,3-dihydropyrrolo[3,4-b]quinolin-1-one (X = H or F).A white slurry of 4-X-3-bromo-2-[1-(alkyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino]-benzonitrile (1.0 equiv) in t-butanol (0.08-1.00 M) was warmed to 45 C and treated with sodium t-butoxide (1.2 equiv). The resulting green solution was heated at 45 C for 3 h. The reaction was cooled to room temperature, partitioned between methylene chloride and water and the organic layer was washed with saturated aqueous sodium bicarbonate and the combined aqueous layers were extracted with methylene chloride. The organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a light tan solid in greater than 80% yield, which was used without further purification.The intermediate compounds were prepared as follows:4-X-3-Bromo-2-[1-(alkyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino]-benzonitrile (X = H or F).2-Amino-3-bromo-4-X-benzonitrile (1.0 equiv) and 1-(alkyl)-4-methoxy-1H-pyrrol-2(5H)-one (2.0 equiv) were combined in acetic acid (0.5-0.8 M benzonitrile in HOAc) and heated to 80 C. Methanesulfonic acid (2.5 equiv) was dissolved in acetic acid (10 M) and added dropwise via syringe over 15 min. The reaction was stirred for 1 h at 80 C and then cooled to rt and placed on a rotary evaporator under high vacuum for 15 min at 55 C to remove the acetic acid. The resulting oil was dissolved in methylene chloride and slowly added dropwise over 20 min to a solution of saturated aqueous sodium bicarbonate at 0-5 C, maintaining the pH value above 8. The resultant precipitate from the biphasic system was separated, washed with water twice and then with hexane once, and was dried at 50 C under high-vacuum to give a tan solid as the title compound in 70-85% yield, which was used without further purification (see Table 8).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-3-bromo-4-fluorobenzonitrile, its application will become more common.

Reference:
Article; Alhambra, Cristobal; Becker, Chris; Blake, Timothy; Chang, Amy; Damewood Jr., James R.; Daniels, Thalia; Dembofsky, Bruce T.; Gurley, David A.; Hall, James E.; Herzog, Keith J.; Horchler, Carey L.; Ohnmacht, Cyrus J.; Schmiesing, Richard Jon; Dudley, Adam; Ribadeneira, Maria D.; Knappenberger, Katherine S.; MacIag, Carla; Stein, Mark M.; Chopra, Maninder; Liu, Xiaodong F.; Christian, Edward P.; Arriza, Jeffrey L.; Chapdelaine, Marc J.; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 2927 – 2938;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 194853-86-6, 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 194853-86-6 as follows.

Potassium carbonate (304 mg, 2 .2 mmol) was dissolved in a minimum amount of water. Next, 4-fluoro-2-trifluoromethylbenzonitrile (378 mg, 2.0 mmol) and trans-4- aminocyclohexanol (460 mg, 4.0 mmol) dissolved in acetonitrile (10 mL) were added. The resulting mixture was then heated at 80C for 3 days. After cooling at room temperature, the mixture was concentrated under vacuum, taken up in ethyl acetate (15 mL), washed with saturated aqueous ammonium chloride (2×10 mL), and washed with water (10 mL). The organic phase was collected and dried over sodium sulfate, filtered, and concentrated under vacuum. The desired product was isolated as a colorless solid (456 mg, 80% yield).

According to the analysis of related databases, 194853-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INTERVET INTERNATIONAL B.V.; WO2009/77527; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 6306-60-1,Some common heterocyclic compound, 6306-60-1, name is 2-(2,4-Dichlorophenyl)acetonitrile, molecular formula is C8H5Cl2N, 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.

Preparation of alpha-(2,4-dichlorophenyl)-alpha-hydroxymethylene acetonitrile 0.6 g of metal sodium was added to dry ethanol to obtain an ethanol solution of sodium ethoxide. Then, a mixed liquid comprising 37.2 g of 2,4-dichlorophenyl acetonitrile and 22.2 g of ethyl formate, was added thereto under heating to 70 C. After the addition, the mixture was further heated and refluxed for 2 hours and then, left to stand for 1 day. The reaction solution was cooled to 0 C. and then subjected to filtration. After washing with diethyl ether, the sodium salt collected by filtration was added to 130 ml of distilled water, and 9 ml of acetic acid was dropwise added thereto under cooling at 0 C. After the dropwise addition, the mixture was stirred at room temperature for about 30 minutes. Then, the formed precipitate was collected by filtration and washed with water. It was dried to obtain 31.7 g (yield: 74%) of the desired product. Melting point: 162-163 C.

The synthetic route of 6306-60-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US6048823; (2000); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 218632-01-0, name is 3-Fluoro-4-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 218632-01-0, name: 3-Fluoro-4-nitrobenzonitrile

Synthesis of 3-((3,4-dimethylphenyl)amino)-4-nitrobenzonitrile To 3,4-dimethylaniline (4.4 g, 35.9 mmol) in THF (100 mL) was added sodium hydride (95% in mineral oil, 1.34 g, 55.8 mmol) and stirred for 1 hour. 3-Fluoro-4-nitrobenzonitrile (5.0 g, 30.1 mmol) was added and the reaction mixture was heated to reflux for 8 hours. Reaction mixture was cooled to room temperature, water was added and filtered through silica gel, washed with 5% THF in hexane and concentrated in vacuo. The crude mixture was purified by flash column chromatography with 5-10% THF in hexane to give 3-((3,4-dimethylphenyl)amino)-4-nitrobenzonitrile (3.4 g, 36% yield) as an orange powder.

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

Reference:
Patent; Universal Display Corporation; KWONG, Raymond; LAM, Sze Kui; LAM, Siu Tung; TSANG, Kit Yee; LEE, Chi Hang; SZIGETHY, Geza; (159 pag.)US2016/218303; (2016); A1;,
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. 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 1009-35-4

[0222] To a solution of 4-fluoro-3-nitrobenzonitrile (0.100 g, 0.600 mmol) and l-(2-chloro~6- fluorobenzyl)piperazine (0.102 g, 0.446 mmol) in ACN (1 mL) was added K2CO3 (0.185 g, 1.338 rnmol). The reaction mixture was heated to 80°C for 3 hours and then diluted with water (3 mL). Tlie liquid phase was decanted and tlie solid phase was washed with water and dried in a vacuum oven at 70°C for 4 hours to give the title compound, which was used without further purification.

The synthetic route of 1009-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 64829-31-8, A common heterocyclic compound, 64829-31-8, name is 3-Methoxy-4-methylphenylacetonitrile, molecular formula is C10H11NO, 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.

Step A: Preparation of 2-(3-Hydroxy-4-methylphenyl)acetonitrile: To a stirred solution of 2-(3-methoxy-4-methylphenyl)acetonitrite (5 g, 31 mmol) in dry CH2Cl2 (20 ml) was added drop wise BBr3 (1M in CH2Cl2, 10.02 g, 40 mmol) at-78C under argon. The reaction mixture was stirred at the same temperature for 2 hours and then at 0C for 5 hours or until all the starting material is consumed, quenched with ice, extracted with EtOAc (30 ml X 3), the combined organic layer was washed carefully with sat NaHCO3, brine and dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: methyl acetate 4:1?CH2Cl2: hex 1:1) to give the title compound as an off white 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:
Patent; Wellstat Therapeutics Corporation; O’NEIL, James, Dennen; SHARMA, Shalini; ARUDCHANDRAN, Ramachandran; EP2282736; (2015); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 134227-45-5, These common heterocyclic compound, 134227-45-5, name is 3,4,5-Trifluorobenzonitrile, 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.

To a solution of 2-(4-(1H-pyrazol-1-yl)benzyl)-7-hydroxyisoindolin-1-one (0.20 g) obtained in Reference Example 14 in DMF (2 mL) was added potassium carbonate (0.27 g), and the mixture was stirred under an argon atmosphere at room temperature for 5 min. To the reaction solution was added 3,4,5-trifluorobenzonitrile (0.11 g) in DMF (2 mL), and the mixture was stirred at 90C overnight. The reaction mixture was diluted with water and ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by NH silica gel chromatography (hexane-ethyl acetate), and solidified with hexane-ethyl acetate to give the title compound (0.014 g). MS: [M+H]+ 443.1 1H NMR (300 MHz, CDCl3) delta 4.29 (2H, s), 4.77 (2H, s), 6.45-6.49 (1H, m), 6.83 (1H, d, J = 8.3 Hz), 7.17 (1H, d, J = 7.5 Hz), 7.34 (2H, d, J = 7.2 Hz), 7.37-7.48 (3H, m), 7.64-7.70 (2H, m), 7.72 (1H, d, J = 1.9 Hz), 7.91 (1H, d, J = 2.3 Hz).

The synthetic route of 134227-45-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; SUZUKI, Shinkichi; YAMADA, Masami; KAMATA, Makoto; KOJIMA, Takuto; FUJIMORI, Ikuo; SHIMOKAWA, Kenichiro; EP2921480; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 114344-60-4, name is 2-Amino-3-bromobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Amino-3-bromobenzonitrile

General procedure: 9-Amino-4-X-5-bromo-2-(alkyl)-2,3-dihydropyrrolo[3,4-b]quinolin-1-one (X = H or F).A white slurry of 4-X-3-bromo-2-[1-(alkyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino]-benzonitrile (1.0 equiv) in t-butanol (0.08-1.00 M) was warmed to 45 C and treated with sodium t-butoxide (1.2 equiv). The resulting green solution was heated at 45 C for 3 h. The reaction was cooled to room temperature, partitioned between methylene chloride and water and the organic layer was washed with saturated aqueous sodium bicarbonate and the combined aqueous layers were extracted with methylene chloride. The organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a light tan solid in greater than 80% yield, which was used without further purification.The intermediate compounds were prepared as follows:4-X-3-Bromo-2-[1-(alkyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino]-benzonitrile (X = H or F).2-Amino-3-bromo-4-X-benzonitrile (1.0 equiv) and 1-(alkyl)-4-methoxy-1H-pyrrol-2(5H)-one (2.0 equiv) were combined in acetic acid (0.5-0.8 M benzonitrile in HOAc) and heated to 80 C. Methanesulfonic acid (2.5 equiv) was dissolved in acetic acid (10 M) and added dropwise via syringe over 15 min. The reaction was stirred for 1 h at 80 C and then cooled to rt and placed on a rotary evaporator under high vacuum for 15 min at 55 C to remove the acetic acid. The resulting oil was dissolved in methylene chloride and slowly added dropwise over 20 min to a solution of saturated aqueous sodium bicarbonate at 0-5 C, maintaining the pH value above 8. The resultant precipitate from the biphasic system was separated, washed with water twice and then with hexane once, and was dried at 50 C under high-vacuum to give a tan solid as the title compound in 70-85% yield, which was used without further purification (see Table 8).

The synthetic route of 114344-60-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alhambra, Cristobal; Becker, Chris; Blake, Timothy; Chang, Amy; Damewood Jr., James R.; Daniels, Thalia; Dembofsky, Bruce T.; Gurley, David A.; Hall, James E.; Herzog, Keith J.; Horchler, Carey L.; Ohnmacht, Cyrus J.; Schmiesing, Richard Jon; Dudley, Adam; Ribadeneira, Maria D.; Knappenberger, Katherine S.; MacIag, Carla; Stein, Mark M.; Chopra, Maninder; Liu, Xiaodong F.; Christian, Edward P.; Arriza, Jeffrey L.; Chapdelaine, Marc J.; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 2927 – 2938;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts