Month: February 2021

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 10406-25-4,Some common heterocyclic compound, 10406-25-4, name is 4-(Aminomethyl)benzonitrile, molecular formula is C8H8N2, 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: Carborane-1-carboxylic acid (1.0 equiv) and COMU (1.1 equiv) dissolved in DMF, acetone or ethylacetate were reacted with the amine (1.2 equiv) and N,N-diisopropylethylamine (DIPEA, 2.0 equiv) dissolved in DMF, acetone or ethylacetate for 25minat room temperature and purified using the eluent ratio given below. Synthetic details of the optimized procedure in DMF and analytical data of compounds not listed below have recently been reported [33].

The synthetic route of 10406-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Scholz, Matthias S.; Wingen, Lukas M.; Brunst, Steffen; Wittmann, Sandra K.; Cardoso, Ian L.A.; Weizel, Lilia; Proschak, Ewgenij; European Journal of Medicinal Chemistry; vol. 185; (2020);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 3672-47-7, A common heterocyclic compound, 3672-47-7, name is 3-(4-Methoxyphenyl)-3-oxopropanenitrile, molecular formula is C10H9NO2, 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.

General procedure: Fresh cells and lyophilised cells of Rhodotorula rubra MIM147 were used 20gL-1 dry weight re-suspended in phosphate buffer or in tap water with 50gL-1 of glucose; then the substrates 1, 3-10 were dissolved in DMSO and added at 2gL-1 concentration. For substrate 1, biotransformations were also carried out at 4, 6 or 10gL-1 concentration.

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; Rimoldi, Isabella; Facchetti, Giorgio; Nava, Donatella; Contente, Martina Letizia; Gandolfi, Raffella; Tetrahedron Asymmetry; vol. 27; 9-10; (2016); p. 389 – 396;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 40497-11-8, name is Ethyl 2,3-dicyanopropanoate, 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 40497-11-8, Application In Synthesis of Ethyl 2,3-dicyanopropanoate

In a 250 mL round bottom three-necked flask, 0.01 mol of 2-methylaniline and a small amount of ethanol were added,3.0 mL (0.035 mol) of concentrated hydrochloric acid was added dropwise under ice-cooling with stirring.0.018 mol of sodium nitrite was dissolved in 10 mL of water,Slowly drop into the flask, drop finishedAfter reaction 0.5h yellow diazonium salt solution.0.01 mol of ethyl 2,3-dicyanopropionate was added to a three-necked flask,The prepared diazonium salt solution was dropped into the flask,After dropping the reaction for 2 h.Adding ammonia,Adjust the pH to 9-10,Reaction at room temperature for 2h.After completion of the reaction, the reaction mixture was extracted with 40 mL of dichloromethane,The organic layer was washed with water (2 x 30 mL)Washed with saturated sodium chloride solution (1 x 40 mL)Dried over anhydrous magnesium sulfate,A portion of the solvent was evaporated under reduced pressure to crystallize 1.30 g of product,Yield 66.7%

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; Nanjing University of Technology; Wan, Rong; Wu, Shaohua; Guo, Chunwei; Wang, Xinlin; Chen, Fuli; Han, Zhenyu; Fu, Xiaohuan; (13 pag.)CN105820167; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts