Month: June 2021

Synthetic Route of 20099-89-2,Some common heterocyclic compound, 20099-89-2, name is 4-(2-Bromoacetyl)benzonitrile, molecular formula is C9H6BrNO, 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-I: 4-(2-amino-4-hydroxy-7H-pyrrolo [2, 3-d] pyrimidin-6-yl) benzonitrile (XI- 10- I): A mixture of 2, 6-diaminopyrimidin-4-oI ( 1 g, 7.93 mmol) and NaOAc (0.846 g, 10.31 mmol) in water (180 mL) was heated to 100 C for 20 minutes. To this was added a suspension of 4-(2-bromoacetyl) benzonitrile (2.2 gm, 8.73 mmol) [prepared according to procedure mentioned in J.Med. Chem, 201 1 , 54(12), 4042-4056] in MeOH (25 mL) and heated overnight at 100 C. After completion of reaction, the reaction mixture was cooled to 0 C. Resultant solid product was filtered off and dried under reduced pressure to provide title compound Chi-10-Iota (1.2 g, 100%). LCMS: mlz 252 (M+l )+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(2-Bromoacetyl)benzonitrile, its application will become more common.

Reference:
Patent; ADVINUS THERAPEUTICS LIMITED; THAKKAR, Mahesh; KOUL, Summon; BHUNIYA, Debnath; MOOKHTIAR, Kasim; KURHADE, Santosh; MUNOT, Yogesh; WO2013/157022; (2013); A1;,
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Application of 145689-34-5, 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. 145689-34-5, name is 2-(2,3-Difluorophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of (2,3-difluorophenyl)acetonitrile (40.5 g, 265 mmol), ethyl acrylate (24 mL, 221 mmol), and hydroquinone (50 mg, 0.45 mmol) was added KOH (2 M in MeOH, 2.0 mL, 4.0 mmol) and the resulting mixture was heated at 160 C for 16 h and then allowed to cool to ambient temperature. The crude mixture was purified by silica gel chromatography, eluting with a gradient of hexanes:EtOAc – 100:0 to 50:50, to give the title compound. MS: mlz = 207.9 (M – OEt).

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-(2,3-Difluorophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BELL, Ian, M.; FRALEY, Mark, E.; GALLICHO, Steven, N.; MITCHELL, Helen, J.; WANG, Chang; WO2012/129014; (2012); A1;,
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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. 6629-04-5, name is N-Cyanoacetylurethane, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: N-Cyanoacetylurethane

General procedure: To the mixture of substituted anilines (0.08mol), concentrated hydrochloric acid (45.0mL) and water (120.0mL), aqueous solution of NaNO2 (60.0mL, 0.11mol) was added drop-wise under stir at a rate that the temperature below 0C, and the reaction mixture was stirred for 0.5h. A mixture of ethyl (2-cyanoacetyl)carbamate (13.7g, 0.09mol) and sodium acetate (24.0g, 0.27mol) in ethanol (400.0mL) was added drop-wise to the resulting diazonium salt solution below 0C and stirred for a further 2h. The precipitate was collected by filtration and washed with water (40.0 mL×2), dried to give compounds 7a-f.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 6629-04-5.

Reference:
Article; Zhao, Sijia; Zhang, Yu; Zhou, Hongyang; Xi, Shuancheng; Zou, Bin; Bao, Guanglong; Wang, Limei; Wang, Jiao; Zeng, Tianfang; Gong, Ping; Zhai, Xin; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 37 – 50;,
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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. 3672-47-7, name is 3-(4-Methoxyphenyl)-3-oxopropanenitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H9NO2

General procedure: Benzoyl acetonitrile (1, 0.5 mmol), cyclic 2-diazo-1,3-dicarbonyl compound (2, 1.25 mmol), [RhCp*Cl2]2 (0.025 mmol), CsOAc (0.25 mmol), Cu(OAc)2*H2O (1.0 mmol) and DCE (2 mL) were sequentially charged into a reaction tube. The tube was then sealed and the mixture was stirred at 80 C. Upon completion, it was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (10 mL * 3). The combined organic phase was dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleum ether/ethyl acetate (5:1) as eluent to afford 3.

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; Zhang, Beibei; Li, Bin; Guo, Chenhao; Zhang, Xinying; Fan, Xuesen; Tetrahedron Letters; vol. 59; 32; (2018); p. 3094 – 3099;,
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Reference of 243128-37-2, The chemical industry reduces the impact on the environment during synthesis 243128-37-2, name is 4-Fluoro-3-methoxybenzonitrile, I believe this compound will play a more active role in future production and life.

To a stirred solution of 51 (16.0 g, 105.8 mmol) in dry diethyl ether (1000 mL) at -78 C was added Ti (O?Pr)4 (35.1 mL, 116.3 mmol). EtMgBr (3M soln. in Et20, 70.5 mL, 211.6 mmol) was added dropwise under nitrogen atmosphere to the reaction mixture and stirred at room temperature at for 1 h. BF3.OEt2 (26.5 mL, 211.6 mmol) was added dropwise to the reaction mixture and stirred at room temperature for 1.5 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with iN HC1 and stirred for 10 mm. The reaction mixture was neutralized with aqueous NaOH and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 52. Yield: 8.0 g, 41%. ?HNMR (400 IVIFIz, DMSO-d6) 0.87 -0.92 (m, 4H), 2.33 (br s, 2H) 3.83 (s, 3H), 6.76-6.80 (m, 1 H), 7.02 -7.09 (m, 1H), 7.13 (d, J= 7.83 Hz, 1H).

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-Fluoro-3-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; LEWIS, Michael; (300 pag.)WO2018/98204; (2018); A1;,
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Synthetic Route of 94088-46-7, These common heterocyclic compound, 94088-46-7, name is 2-Fluoro-6-methoxybenzonitrile, 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.

In a round bottom flask, 5 cm3 water,0.453 g of 2-fluoro-6-methoxybenzonitrile (0.003 mol), 0.621 g of 1-(4-nitrophenyl)piperazine (0.003 mol), 0.387 gof DIPEA (0.003 mol), 0.096 g of TBAB (0.0003 mol), and 0.318 g of Na2CO3(0.003 mol) was taken. Reaction was carried out at reflux for 3 h. Then reaction mixture was cooled and extracted with ethyl acetate. The product was purified by flash chromatography on silica using hexane-ethyl acetate mobile phase to afford 0.42 g 16 (42%). M.p.:160-164 C; 1H NMR (400 MHz, CDCl3):delta = 3.939 (s, 4H),3.649 (s, 4H), 3.953 (s, 3H), 6.630 (d, J = 4 Hz, 2H), 6.893(d, J = 8 Hz, 2H), 7.460 (t, J = 8 Hz, 1H), 8.165 (d, J = 8 Hz,2H) ppm; 13C NMR (100 MHz, CDCl3):delta = 46.1 (CH2), 46.8(CH2), 47.2 (CH2), 50.9 (CH2), 56.1 (OCH3), 104.8 (CCN),110.5 (CH), 112.9 (CH), 115.7 (CN), 129.9 (CH), 134.4(CH), 138.8 (CNO2), 154.7 (C), 156.6 (C), 163.0 (CO) ppm; IR (KBr): =nu 2886, 2215, 1594, 1480, 1322, 1600, 1508,1458, 1266 cm-1; ESI-MS: m/z = 339 (MH+).

The synthetic route of 94088-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ghorpade, RamaRao; Kumar, Deo; Nayak, Sabita; Acharya, Badri Narayan; Monatshefte fur Chemie; vol. 150; 7; (2019); p. 1335 – 1347;,
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Application of 612-24-8, 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. 612-24-8, name is 2-Nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Nitro aromatic (1.0 mmol), B2(OH)4 (5.0 equiv, 5.0 mmol), and H2O (3.0 mL) were added in a10 mL tube. The reaction mixture was stirred at 80 C for 8 h. When the reaction was completemonitored by TLC, the mixture was cooled to room temperature, extracted with ethyl acetate (3 ×20 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, andconcentrated under reduced pressure. The residue was purified by silica gel columnchromatography.

The synthetic route of 2-Nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Danyi; Zhou, Yanmei; Zhou, Haifeng; Liu, Sensheng; Liu, Qixing; Zhang, Kaili; Uozumi, Yasuhiro; Synlett; vol. 29; 13; (2018); p. 1765 – 1768;,
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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. 3939-09-1, name is 2,4-Difluorobenzonitrile, A new synthetic method of this compound is introduced below., name: 2,4-Difluorobenzonitrile

To a solution of lH-l,2,3-triazole (3.5 g, 50.7 mmol) in tetrahydrofuran (10 mL) and dimethylformamide (20 mL) was added, portionwise, NaH (1.3 g, 51 mmol, 95%). The mixture was stirred at room temp for 30 min. 2,4-Difluorobenzonitrile (7.6 g, 55 mmol) was added and the mixture stirred at 85 C for 3 h. The white mixture was concentrated and purified by flash chromatography eluting with 0% to 10% ethyl acetate/hexanes to give intermediates 77 and 78.Intermediate 774-Fluoro-2-l,2,3-triazol-2-yl-benzonitrile. White needles (0.34 g, 3% yield).IH-NMR (300 MHz, CDCl3) delta ppm: 7.92 (2H, s), 7.88-7.79 (2H, m), 7.19-7.12 (IH, m). LCMS [M+H]+ calcd for C9H6N4F: 189.05; found: 189.12. Intermediate 782-Fluoro-4-l,2,3-triazol-2-yl-benzonitrile. White solid (0.097 g, 1% yield).1H-NMR (300 MHz, CDCl3) delta ppm: 8.03-7.95 (2H, m), 7.86 (2H, s), 7.74-7.69 (IH, m).

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; BRISTOL-MYERS SQUIBB COMPANY; WO2007/64316; (2007); A1;,
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Related Products of 77326-36-4,Some common heterocyclic compound, 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, molecular formula is C7H5FN2, 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.

Add 2-amino-6-fluorobenzonitrile (136 mg, 1 mmol), benzyl alcohol (108 mg, 1 mmol),Fe (NO3) 3 · 9H2O (40.4 mg, 0.10 mmol), TEMPO (15.6 mg, 0.10 mmol),t-BuOK (224mg, 2equiv) and 2mL of toluene were sequentially added to a 25mL reaction tube, and the reaction mixture was reacted under reflux for 12h and cooled to room temperature;Ethyl acetate was added to dilute the reaction solution, and then washed three times with water, and then the organic phase was separated.After drying over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product;The crude product was purified by column chromatography with petroleum ether / ethyl acetate, yielding 78%.

The synthetic route of 77326-36-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing University of Science and Technology; Li Bindong; Hu Yongke; (12 pag.)CN110357823; (2019); A;,
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Electric Literature of 120315-65-3, 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. 120315-65-3, name is 4-Bromo-3-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 0.17 mmol lnt2.1 in 1.33 mL NMP was combined with 0.44 mmol 4-Bromo-3-methoxybenzonitrile (48.6 mg, 2.6 eq), 0.04 mmol Pd2(dba)3 (36.6 mg, 0.23 eq), 0.12 mmol rac-BINAP (74.7 mg, 0.7 eq) and 0.25 mmol NaOtBu (24.03 mg, 1.5 eq) in a sealed vial and heated at 170 C under microwave irradiation for 2 h. After cooling, the solution was filtered and subjected to preparative HPLC to give 4.7 mg of the title compound. UPLC-MS: RT = 1.15 min; m/z (ES+) 400.5 [MH+]; required MW = 399.5.

The synthetic route of 4-Bromo-3-methoxybenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Schering Pharma AG; EP2343297; (2011); A1;,
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