Category: nitriles-buliding-blocks

Electric Literature of 6621-59-6, A common heterocyclic compound, 6621-59-6, name is 6-Bromohexanenitrile, molecular formula is C6H10BrN, 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.

6-Bromocapronitrile (1.19ml, 9.00mmol) and 3-buten-1-ol (946ul, H .Ommol) were added to a stirred solution of potassium hydroxide (6.16g, 110mmol) and tetra-butylammonium bromide (434mg, 1.35mmol) in water (6ml) and dichloromethane (2ml). The reaction was stirred at room temperature for 4 days and then washed with diethyl ether (2x50ml). The combined organics were washed with water (3x30ml), dried (magnesium sulphate) and the solvent removed in vacuo to furnish the title compound as a colourless oil, 1.48g. LRMS: m/z 168 [M+H]+.

The synthetic route of 6621-59-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; WO2007/107828; (2007); A2;,
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Adding a certain compound to certain chemical reactions, such as: 1503-49-7, name is 4-Benzoylbenzonitrile, 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 1503-49-7, Quality Control of 4-Benzoylbenzonitrile

To a vial containing 4-benzoylbenzonitrile (0.181 g, 0.873 mmol; prepared according to the procedure described by L.J. omicronomicronbetaepsiloneta and K. Ghosh, Angew. Chem. Int. Ed. 2001, 40, 3458), NBS (0.171 g, 0.961 mmol), p-toluenesulfonic acid monohydrate (0.083 g, 0.437 mmol) and palladium (II) acetate (0.020 g, 0.087 mmol), was added DCE (10 mL). The vial was briefly purged with N2 and then it was sealed and the mixture was stirred at 80C (block temperature) overnight. The cooled mixture was evaporated and the residue was taken up in a minimum volume of DCM and then adsorbed on a silica gel pre-column. Flash chromatography (ISCO/ 0-50% EtOAc-hexane) gave 4-benzoyl-2- bromobenzonitrile (0.138 g, 55.2% yield) as a white crystalline solid. LC-MS (Method J): 1.272 min, [M + H]+ = no ion observed; H NMR (400 MHz, OMSO-d6) delta ppm 8.11 (d, J= 7.8 Hz, 1H), 8.09 (d, J= 1.2 Hz, 1H), 7.81 (dd, J= 1.6, 7.8 Hz, 1H), 7.76 (d, J= 7.4 Hz, 2H), 7.72 (t, /= 7.4 Hz, 1H), 7.58 (t, /= 7.6 Hz, 2H).

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; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
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57381-56-3, name is 2-Chloro-5-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. COA of Formula: C7H3ClFN

Preparation 13: 1-[2-ChIoro-5-(4-methyI-piperazin-1-yl)-phenyl]-ethanone; STEP A; A mixture of 2-chloro-5-fluoro-benzonitrile (1 g, 6.43 mmol), K2CO3 (2.66 g, 19.3 mmol) and 1-methyl-piperazine (1.02 g, 10.26 mmol) in DMSO (14 ml) was stirred at 1000C overnight and then further 1-methyl-piperazine (1.02 g, 10.26 mmol) was added. The mixture was stirred at 1000C overnight and then partitioned between water and Et2O. The organic phase was extracted with 1 M HCI and the aqueous layer was brought to basic conditions with NH4OH and extracted with DCM. The organic phase was dried over Na2SO4 and evaporated in vacuo to give 1 g of 2- chloro-5-(4-methyl-piperazin-1-yl)-benzonitrile. Y= 66%

The synthetic route of 57381-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAC S.R.L.; WO2007/113249; (2007); A2;,
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Synthetic Route of 151-18-8, The chemical industry reduces the impact on the environment during synthesis 151-18-8, name is 3-Aminopropanenitrile, I believe this compound will play a more active role in future production and life.

Example 386 N-(3-(((2-cyanoethyl)amino)carbonyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-6-methylpyridine-2-carboxamide 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 186-187 C. 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; Tsukamoto, Tetsuya; Yamamoto, Takeshi; Tokunoh, Ryosuke; Kawamoto, Tomohiro; Okura, Masahiro; Kori, Masakumi; Murase, Katsuhito; US2009/156582; (2009); A1;,
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Related Products of 16932-49-3, 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. 16932-49-3 name is 2,6-Dimethoxybenzonitrile, 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.

General procedure: :2,6-dimethoxybenzonitrile (501 mg, 3.07 mmol) and4-amino-7-chloroquinoline (548 mg, 3.07 mmol) were dissolved together in 20 mLof anhydrous tetrahydrofuran. The vesselwas swept with nitrogen and chilled in an ice-water bath. Ethereal 3.0 M ethyl magnesium bromide (2.05 mL,6.14 mmol) was added dropwise over 3 min.After briefly forming an off-white solid suspended in a yellow solution,within minutes the mixture became a dark amber homogenous solution with someoff-white solid material remaining. Thevessel was placed in a 75 C oil bath for 21 h before diluting with 60 mL ofwater. The pH was decreased to ca. 14 byaddition of 4 pellets of NaOH. Themixture was then extracted with 60 mL of ethyl acetate, using solid NaCl tofacilitate partitioning. The organicswere dried over MgSO4 and concentrated to 1.27 g of a crude brownoily paste containing mostly unreacted starting materials. Flash chromatography (150 mL silica gel, 50%ethyl acetate / hexane, then neat ethyl acetate, then 10% methanol in ethylacetate) returned 100 mg (9.6%) ofN-(7-chloroquinolin-4-yl)-2,6-dimethoxybenzimidamide (G).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dimethoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Hershberger, Paul M.; Hedrick, Michael P.; Peddibhotla, Satyamaheshwar; Mangravita-Novo, Arianna; Gosalia, Palak; Li, Yujie; Gray, Wilson; Vicchiarelli, Michael; Smith, Layton H.; Chung, Thomas D.Y.; Thomas, James B.; Caron, Marc G.; Pinkerton, Anthony B.; Barak, Lawrence S.; Roth, Gregory P.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 262 – 267;,
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Reference of 4640-66-8, 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. 4640-66-8, name is 4-Chlorophenacylcyanide belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a 0.5-2.0ml vial with 1 mmol ketone (1 eq) issolved in 2-pentanol (1.66 M) was added 1.1 eq of aromatic aldehyde and catalytic piperidine (0.08 eq), stirring vigorously. After heating under muWave for 15min at 120 C, the reaction was cooled to r.t. and precipitate was vacuum filtered and washed with minimal, cold hexanes. After drying under vacuum, solid was analyzed via NMR, IR, and mp.

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

Reference:
Article; Deshpande, Shyam J.; Leger, Paul R.; Sieck, Stephen R.; Tetrahedron Letters; vol. 53; 14; (2012); p. 1772 – 1775;,
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Adding a certain compound to certain chemical reactions, such as: 905710-66-9, name is 4-Bromo-3-(hydroxymethyl)benzonitrile, 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 905710-66-9, Formula: C8H6BrNO

To a solution of 4-bromo-3-(l -hydroxy ethyl)benzonitrile (0.95 g, 0.0045 mol) in dichloromethane (CH2CI2; 10 mL) at 0 C were added NN-diisopropylethylamine (DIPEA; 2.0 g, 0.0157 mol) and methyl chloromethyl ether (MOMCl; 0.72 g, 0.009 mol) slowly. The resulting mixture was stirred at room temperature overnight. The reaction mass was quenched with H2O and extracted with CH2CI2. The organic layer was washed with H2O and brine, dried over Na2S04 and concentrated to provide the crude product. Purification by flash column chromatography (S1O2; gradient of 0-15 % EtOAc in hexane) gave the title compound as a colorless oil (1 g, 90%).

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-Bromo-3-(hydroxymethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DOW AGROSCIENCES LLC; BRAVO-ALTAMIRANO, Karla; CASTELLO, Olena; GRUBER, Joseph M.; MARKLEY, Lowell; RIAR, Dilpreet S.; ROTH, Joshua; YAP, Maurice C.; (62 pag.)WO2018/156554; (2018); A1;,
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Synthetic Route of 78881-21-7, These common heterocyclic compound, 78881-21-7, name is 4-Amino-3-methylbenzonitrile, 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.

A mixture of [6-CHLORO-4-ISOPROPYL-N- (TETRAHYDRO-PYRAN-4-YLMETHYL)-NICOTINAMIDE] (Description 8) (100mg), 4-amino-3-methyl benzonitrile (2eq), cesium carbonate (168mg), tris [(DIBENZYLIDENEACETONE)] palladium (0) (Pd2 (dba) [3)] (3.4mg), 4,5-bis (diphenylphosphino)- 9, 9-dimethylxanthene (Xantphos) (2.3mg) in 1,4-dioxane [(1ML)] was irradiated under microwave conditions at [150C] for 30 minutes. Further quantities of cesium carbonate (168mg), Pd2 (dba) 3 (3.4mg) and Xantphos (2.3mg) were added and the mixture was again subjected to microwave conditions at [150C] for 30 minutes. Ethyl acetate was added and the mixture was washed with water. The ethyl acetate layer was dried (sodium sulphate) and the solvent was removed under reduced pressure. The residue was purified using MDAP to give the title compound (20mg) NMR [(MEOD)] [8] 1.25 (6H, d), 1.29-1. 43 (2H, m), 1.70 (2H, d), 1.81-1. 93 [(1 H,] m), 2.3393H, s), 3.21-3. 50 (5H, m), 3.98 (2H, dd), 7.01 (1 H, s), 7.49 (1 H, dd), 7.55 (1 H, bs), 8.02 (1 H, d), 8.09 [(1H,] s) LC/MS, t = 2.89 min, Molecular ion observed [[MH+]] = 393 consistent with the molecular formula [C23H28N402]

The synthetic route of 78881-21-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/29026; (2004); A1;,
Nitrile – Wikipedia,
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Synthetic Route of 868-54-2,Some common heterocyclic compound, 868-54-2, name is 2-Aminoprop-1-ene-1,1,3-tricarbonitrile, molecular formula is C6H4N4, 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: Heterocyclic ketene aminals (1 mmol), aryl aldehydes (1.2 mmol), malononitriledimer (1.5 mmol), acetic acid (1 mmol), piperidine (1 mmol) and ethanol (10 mL)were stirred at refluxing for 1 h. After completion of the reaction (confirmed by TLC),the reaction mixture was filtered to afford the crude product, which was furtherwashed with 95% ethanol to give pure product 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Aminoprop-1-ene-1,1,3-tricarbonitrile, its application will become more common.

Reference:
Article; Sun, Feilong; Zhu, Fengjuan; Shao, Xusheng; Li, Zhong; Synlett; vol. 26; 16; (2015); p. 2306 – 2312;,
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These common heterocyclic compound, 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, 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. Recommanded Product: 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile

Experiment 4; The general procedure of Experiment 2 was applied. To the 4-[4-(dimethylamino)-1-(4′-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)-benzonitrile free base solution in 1-propanol was added 0.05 V of water. No toluene or acetic acid was present in the system.An exemplary batch gave molar yield: 29.3%; 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