Month: July 2021

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 4426-11-3 as follows. Safety of Cyclobutanecarbonitrile

Example 275B 1-(1-methyl-1H-benzo[d]imidazol-2-yl)cyclobutanecarbonitrile To a solution of Example 275A (1.90 g, 11.4 mmol) in toluene (30 mL) was added cyclobutanecarbonitrile (1.01 g, 12.5 mmol) and potassium hexamethyldisilazide (34.2 mL, 17.1 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was poured into 1N HCl solution (50 mL) and the aqueous layer was extracted with EtOAc (3*20 mL). The combined layers were washed with brine (100 mL), dried over MgSO4, filtered, and concentrated. The residue was purified by prep. TLC on silicagel (eluted with EtOAc: petroleum ether=1:10) to give the title compound (1.0 g, 4.69 mmol, 41.1% yield) as a white solid. MS: MS (M+H)+; 1H NMR (400 MHz, CDCl3): delta 7.80-7.78 (m, 1H), 7.36-7.30 (m, 3H), 3.83 (s, 3H), 3.13-3.05 (m, 2H), 2.99-2.92 (m, 2H), 2.48-2.41 (m, 1H), 2.24-2.18 (m, 1H).

According to the analysis of related databases, 4426-11-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AbbVie Inc.; Bayburt, Erol K.; Clapham, Bruce; Cox, Phil B.; Daanen, Jerome F.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2013/131036; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 96606-37-0,Some common heterocyclic compound, 96606-37-0, name is 2,4,6-Trifluorobenzonitrile, molecular formula is C7H2F3N, 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 analogy to GP1a, 5 g of 2,4,6-trifluorobenzonitrile (31.83 mmol, 1 eq; commercially available) and 4.45 ml of 2-((R)-2,2-Dimethyl-[1 ,3]dioxolan-4-yl)-ethanol (31.83 mmol, 1 eq; commercially available) were dissolved in 150 ml of THF, treated with 2.78 g sodium hydride (62.66 mmol; 2 eq.) and stirred at rt for 2 h. The reaction mixture was poured onto 50 ml of water and extracted three times with 100 ml of ethyl acetate each. The organic layer was washed twice with brine, dryed over sodium sulfate, filtered off to afford 5.21 g (57.79% yield, 18.39 mmol) of the desired product.1H-NMR (dbeta-DMSO; 300 MHz): 6.52 – 6.57 (m, 2 H); 4.30 – 4.36 (m, 1 H); 4.10 – 4.23 (m, 3 H); 3.67 (dd, 1 H); 2.11 – 2.20 (m, 1 H); 2.00 – 2.08 (m, 1 H); 1.42 (s, 3 H); 1.35 (s, 3 H).MS (ESI): [M+H]+ = 284.

The synthetic route of 96606-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; BAYER HEALTHCARE AG; WO2008/138639; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 33279-01-5, The chemical industry reduces the impact on the environment during synthesis 33279-01-5, name is 3-Oxopentanenitrile, I believe this compound will play a more active role in future production and life.

Example 57A; 5-ethyl-[ 1 ,2,4]triazolo[ 1 ,5-a]pyrimidin-7-amineA mixture of 3-oxopentanenitrile (1.0 g, 10.3 mmol) and 3-amino-l,2,4-triazole (0.91 g, 10.8 mmol) in 10 mL of acetic acid was heated in a pressure tube at 150 0C for 24h. The reaction mixture was allowed to cool to room temperature, and solvent was removed in vacuo. The solid was removed via filtration. The filtrate partially solidified upon standing at room temperature, and the solid was collected via filtration to give the title compound (200 mg, 12% yield).

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

Reference:
Patent; ABBOTT LABORATORIES; WO2008/134690; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 6393-40-4, name is 4-Amino-3-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 6393-40-4, category: nitriles-buliding-blocks

3-Nitro-4-aminobenzonitrile (3.00 g) was dissolved in ethanol (300 ml) and added with stannous chloride dihydrate (20.7 g) and the whole was heated to 60C. Sodium borohydride (348 mg) was gradually added thereto and the whole was stirred overnight at 60C. After completion of the reaction, the resultant was added with water (300 ml) and neutralized with a 5 mol/l sodium hydroxide aqueous solution. After ethanol was distilled off under reduced pressure, the aqueous layer was added with ethyl acetate for extraction. The organic layer was washed with a saturated saline solution and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was recrystallized, thereby obtaining the subject compound (1.11 g) as a brown crystal. MS(EI):m/z=133[M]+ 1H-NMR(500MHz,CDCl3):delta=6.68(1H,d,J=8,1Hz),6.95(1H,s),7.05(1H,d,J=8.1Hz).3-Nitro-4-amino-benzonitrile (4.38 g) was dissolved in ethanol (600 ml) and added with stannous chloride dihydrate (34.6 g) and the whole was heated to 60C. Sodium borohydride (366 mg) was gradually added thereto and the whole was stirred overnight at 60C. After completion of the reaction, the resultant was filtrated through Celite and the filtrate was subjected to distillation of the solvent under reduced pressure. The residue was dissolved in chloroform, washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution, and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was allowed to recrystallize (hexane/ethyl acetate), thereby obtaining the subject compound (2.56 g) as a brown crystal. MS (EI) :m/z=133[M]+ 1H-NMR(500MHz,CDCl3):delta=6.68(1H,d,J=8.1Hz),6.95(1H,s),7.05(1H, d,J=8.1Hz).An ethanol solution (300 ml) containing 4-amino-3-nitrobenzonitrile (3.00 g) was added with stannous chloride dihydrate (20.7 g) and then added with sodium borohydride (348 mg) . The whole was stirred overnight at 60C. After that, the resultant was subjected to distillation until the amount of the solution became about 100 ml. The resultant was added with water (100 ml) and a large amount of solid component was generated. The resultant was added with a 5 mol/l sodium hydroxide aqueous solution (42 ml) to adjust to pH 7. The solvent was distilled off. The solid component was filtrated out through Celite and washed with methanol and ethyl acetate in the stated order. The filtrate was again filtrated through Celite and only organic solvent was distilled off under reduced pressure. The remaining aqueous layer was subjected to extraction with ethyl acetate and dried with anhydrous magnesium sulfate , and the solvent was distilled off, thereby obtaining the subject compound (2.29 g) as a khaki crystal.

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-Amino-3-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kureha Corporation; EP1724263; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 332-25-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 332-25-2 name is 4-(Trifluoromethoxy)benzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 2:; To a stirred solution of N,N-diethyl-4-methoxy-2-methyl-benzamide (10.0 g, 45.2 mmol) in THF (150 mL) at -78° C. under nitrogen atmosphere was added t-BuLi (29.2 mL of 1.7M in pentane, 49.7 mmol) dropwise. The resulting red solution was kept at this temperature for additional 10 min before dropwise addition of 4-(trifluoromethoxy)-benzonitrile (9.49 g, 49.7 mmol). The brown solution was stirred at -78° C. for 2 h; tests by LCMS showed incomplete reaction. Thus to the mixture was added an additional amount of 4-(trifluoromethoxy)-benzonitrile (3.38 g, 18.1 mmol) and the resulting mixture was stirred for an additional 1 h. The mixture was then allowed to warm to rt and was quenched by pouring into aqueous 1.0M HCl (50 mL). EtOAc (100 mL) was added and the mixture was shaken and phases were separated. A precipitate occurred within the EtOAc phase which was isolated by filtration and allowed to dry (3.0 g). This 3.0 g of isolated solid was determined to be impure product and was set aside for later purification. The EtOAc filtrate was set aside. The aqueous acid washes were combined and extracted with DCM (3.x.100 mL). The DCM extracts were combined, washed with brine, dried over MgSO4, filtered and concentrated in vacuo. This residue was combined with the original EtOAc filtrate and the combined organics were concentrated to a slurry. A solid was isolated by filtration to give the desired product (8.84 g, 58.0percent yield). LC-MS, MS m/z 336 (M++H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Trifluoromethoxy)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/119461; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, 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 621-50-1, Recommanded Product: 2-(3-Nitrophenyl)acetonitrile

A. (3-Amino-phenyl)-acetonitrile A mixture of (3-nitro-phenyl)-acetonitrile (2.00 g, 12.35 mmol), iron dust (2.07 g, 37.03 mmol) and ammonia chloride (1.96 g, 37.03 mmol) in EtOH (20 mL) and water (4 mL) was refluxed at 85 C. for 1 h. The reaction mixture was filtered through cellite and rinsed with EtOH. The combined filtrate was concentrated and the residue was purified by silica gel column chromatography (20% ethyl acetate in petroleum ether) to afford the title compound (1.57 g, 11.89 mmol, 96% yield) as a pale-yellow solid. MS (ESI) m/z 133.1 [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-(3-Nitrophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Papa, Patrick; Cathers, Brian Edwin; CALABRESE, Andrew Antony; WHITEFIELD, Brandon Wade; BENNETT, Brydon; CASHION, Daniel; MORTENSEN, Deborah; HUANG, Dehua; TORRES, Eduardo; PARNES, Jason; SAPIENZA, John; HANSEN, Joshua; LEFTHERIS, Katerina; CORREA, Matthew; DELGADO, Maria Mercedes; RAHEJA, Neil; BAHMANYAR, Sami; HEGDE, Sayee; NORRIS, Stephen; PLANTEVIN-KRENITSKY, Veronique; US2015/175557; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 501-00-8,Some common heterocyclic compound, 501-00-8, name is 2-(3-Fluorophenyl)acetonitrile, molecular formula is C8H6FN, 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. 3-Fluoro-phenyl-piperidin-4-ylidene-acetonitrile.; To a mixture of 3-fluoro-phenyl-acetonitrile (3.2 g, 24 mmol) and 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (4.0 g, 20 mmol) in THF (100 mL) was added NaHMDS (1.0 M in THF, 24 mL). The mixture was stirred at rt for 16 h, then was diluted with MeOH (16 mL) and concentrated. The residue was diluted with TFA (40 mL) and stirred at rt for 16 h. The mixture was concentrated and the residue was diluted with satd. aq. NaHCO3 (160 mL) and extracted with EtOAc (3×80 mL). The combined organic layers were filtered and concentrated to provide the crude title compound.

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

Reference:
Patent; Bonaventure, Pascal; Carruthers, Nicholas I.; Chai, Wenying; Dvorak, Curt A.; Jablonowski, Jill A.; Rudolph, Dale A.; Seierstad, Mark; Shah, Chandravadan R.; Swanson, Devin M.; Wong, Victoria D.; US2007/100141; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 103146-25-4, 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. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Experiment 33; Experiment 11 was repeated except that a mixture of 1-propanol and acetonitrile (15:85) was used as the solvent in stead of 1-propanol in a total volume of 4.5 V, 0.5 eq of (+)-O,O’-di-p-toluoyl-(S,S)-tartaric acid was used, and the holding time before filtration was 0.5 h.Molar yield: 25.9%, enantiomeric purity: 99.2% S.; Experiment 34; Experiment 11 was repeated except that a mixture of 1-propanol and acetonitrile (85:15) was used as the solvent in stead of 1-propanol in a total volume of 4.5 V, 0.5 eq of (+)-O,O’-di-p-toluoyl-(S,S)-tartaric acid was used, and the holding time before filtration was overnight.Molar yield: 18.5%, enantiomeric purity: 99.4% S.; Experiment 35; Experiment 11 was repeated except that a mixture of 1-propanol and acetonitrile (90:10) was used as the solvent in stead of 1-propanol in a total volume of 4.5 V, 0.5 eq of (+)-O,O’-di-p-toluoyl-(S,S)-tartaric acid was used, and the holding time before filtration was overnight.Molar yield: 29.9%, enantiomeric purity: 99.3% S.

The synthetic route of 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. Lundbeck A/S; US2009/69582; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, 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 63069-50-1, HPLC of Formula: C7H5FN2

3-bromo-5-fluoro-4-nitrobenzonitrile Step 1 : 4-amino-3-bromo-5-fluorobenzonitrile To a solution of 4-amino-3-fluorobenzonitrile (15.0 g, 1 10 mmol) in acetic acid (200 mL) was added a solution of bromine (5.68 mL, 1 10 mmol) in 15 mL of acetic acid. The reaction was stirred at rt overnight. The mixture was concentrated and repeatedly diluted with hexanes and concentrated to azeotropically remove the trace acetic acid. The crude product was suspended in saturated sodium thiosulfate solution and 2 N NaOH. The mixture was stirred for 10 min. The product was then extracted into EtOAc. The combined organics were dried over Na2S04, filtered, and concentrated to provide the crude title comound (19.8 g, 83 % crude yield) as a yellow solid. MS (m/z) 215.0, 217.0 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-3-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl; CHEUNG, Mui; EIDAM, Hilary, Schenck; GOODMAN, Krista, B.; HAMMOND, Marlys; HILFIKER, Mark, A.; PATTERSON, Jaclyn, R.; STOY, Patrick; YE, Guosen; WO2012/174342; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 330792-69-3, 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. 330792-69-3, name is 2-(Methoxy(4-phenoxyphenyl)methylene)malononitrile, This compound has unique chemical properties. The synthetic route is as follows.

80% Hydrazine hydrate (32.5 ml) was added to a mixture of 2-(methoxy(4- phenoxyphenyl)methylene)malononitrile (48 gms) and methanol (192 ml) at 25-30C and stirred for 2 brs at the same temperature. Water was added to the reaction mixture at 25-30C. Cooled the reaction mixture to 0-5C and stirred for 60 mins at the same temperature.Filtered the precipitated solid, washed with water and dried to get the title compound.Yield: 46 gms; Melting range: 172-176C; purity: 96.89%

The chemical industry reduces the impact on the environment during synthesis 2-(Methoxy(4-phenoxyphenyl)methylene)malononitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MSN LABORATORIES PRIVATE LIMITED; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; MADHUSUDHAN, Gutta; SEETHA RAMA SARMA, Peri; (69 pag.)WO2016/170545; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts