Category: nitriles-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 36282-26-5, name is 2-Bromo-4-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 36282-26-5, HPLC of Formula: C7H3BrFN

To a solution of 2-bromo-4-fluorobenzonitrile (0.5 g, 2.50 mmol) and phenol (0.25 g, 2.62 mmol) in DMSO (2 mL), at RT, K2C03 (0.69 g, 5 mmol) was added and the reaction mixture was stirred at RT overnight. Water and Et20 were added to the reaction mixture, the organic phase was washed withwater and saturated NaHCO3, dried and the solvent removed under reduced pressure. Crude materialwas purified by FC on silica gel (eluent: Cy/EA from 100/0 to 90/10) to give 2-bromo-4-phenoxybenzonitrile (p21, 220 mg, y= 32%).1H NMR (CHLOROFORM-d): 6 ppm 7.60 (d, 1 H) 7.42 – 7.51 (m, 2 H) 7.26 – 7.33 (m, 1 H) 7.23 (d, 1 H)7.09 (d, 2 H) 6.98 (dd, 1 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-Bromo-4-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SHIRE INTERNATIONAL GMBH; CREMONESI, Susanna; LUKER, Tim; SEMERARO, Teresa; MICHELI, Fabrizio; (257 pag.)WO2016/42452; (2016); A1;,
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Application of 6575-11-7,Some common heterocyclic compound, 6575-11-7, name is 2-Amino-6-chlorobenzonitrile, molecular formula is C7H5ClN2, 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.

The reaction mixture composed of 5 g of 2-amino-6-chlorobenzonitrile (32.77 mmol), 30% potassium hydroxide (50 mL), and 30% hydrogen peroxide aqueous solution (3 mL) was heat-refluxed for 12 hours, which was then cooled down at room temperature. The aqueous layer was separated by using diethyl ether and then acidized with 12 N HCl (pH: 3-4) to separate an organic layer. The organic layer was washed with saturated brine and then separated, dried (Na2SO4), filtered, and concentrated under reduced pressure. As a result, 5.31 g of the target compound 2-amino-6-chlorobenzoic acid was obtained as a yellow solid (30.95 mmol, yield: 94%). 1H NMR(300 MHz, DMSO-d6) delta 8.24 (s, 2H), 7.00-7.06 (t, J=7.5 Hz, 1H), 6.64 (d, J=8.4 Hz, 1H), 6.56 (d, J=7.8 Hz, 1H).

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-6-chlorobenzonitrile, its application will become more common.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; Lee, Ge Hyeong; Lim, Hee-Jong; Cho, Heeyeong; Park, Woo Kyu; Kim, Seong Hwan; Choi, Jung Hwan; (148 pag.)US2018/105527; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 868-54-2, name is 2-Aminoprop-1-ene-1,1,3-tricarbonitrile, 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 868-54-2, Formula: C6H4N4

General procedure: A mixture of 0.085 g (1 mmol) of piperidine, 0.182 g (1 mmol) of enaminoketone 2, 0.132 g (1 mmol) of 2-aminoprop-1-ene-1,1,3-tricarbonitrile, and 0.106 g (1 mmol) of benzaldehyde in 5 mL of ethanol was stirred at 30-40 for 30 min. On the completion of the reaction (TLC monitoring) the mixture was cooled, the separated precipitate was filtered off, washed with a little 2-propanol.

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-Aminoprop-1-ene-1,1,3-tricarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Alekseeva, A. Yu.; Bardasov; Mikhailov; Ershov; Russian Journal of Organic Chemistry; vol. 53; 8; (2017); p. 1243 – 1248; Zh. Org. Khim.; vol. 53; 8; (2017); p. 1227 – 1232,6;,
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Adding a certain compound to certain chemical reactions, such as: 1000339-52-5, name is 3-Fluoro-2-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 1000339-52-5, Quality Control of 3-Fluoro-2-nitrobenzonitrile

A solution of 3-fluoro-2-nitrobenzonitrile (300 mg, 1 .806 mmol), 2-(tert-butoxy)ethan-1 – amine (233 mg, 1 .987 mmol), and N,N-diisopropylethylamine (0.379 mL, 2.167 mmol) in DMF (20mL) was stirred for 16 hours. The reaction was concentrated, and the resulting residue was purified via silica gel chromatography (0% to 40% EtOAc/hexanes) to afford 3- ((2-(tert-butoxy)ethyl)amino)-2-nitrobenzonitrile (450 mg) as a orange solid. LC-MS (ES) m/z = 264 [M+H]+. NMR (400 MHz, CDCI3): delta 8.39 (br. s., 1 H), 7.49 (dd, J = 7.1 , 8.9 Hz, 1 H), 7.19 (dd, J = 1 .0, 8.9 Hz, 1 H), 7.14 (dd, J = 1 .1 , 7.2 Hz, 1 H), 3.63 – 3.82 (m, 2H), 3.48 (q, J = 5.1 Hz, 2H), 1 .29 (s, 9H).

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-2-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; MEDINA, Jesus Raul; TIAN, Xinrong; NG DI MARCO, Christina; GRAYBILL, Todd L.; HEERDING, Dirk A.; LI, William Hoi Hong; MANGATT, Biju; MARTYR, Cuthbert D.; RIVERO, Raphael Anthony; (570 pag.)WO2019/49061; (2019); A1;,
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Reference of 6609-57-0, These common heterocyclic compound, 6609-57-0, name is 2-Ethoxybenzonitrile, 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-ethoxybenzonitrile (2, 10 g, 68 mmol) in toluene (150 mL) was added AICH3CINH2 (1 eq). The methylchloroaluminum amide was freshly prepared, in-situ; NH4CI (0.535 g, 10 mmol) was dissolved in dry toluene (10 mL) at 000 and trimethylaluminum (2 M in toluene, 5.0 mL, 10 mmol) was added and the reaction was warmed to r.t. and stirred for 1 hour to give theAICH3CINH2, which was used directly. The mixture was stirred at 80 00 for 6 hours. The reaction mixture was concentrated under vacuo to give crude I24a (8.42 g, 75.4% yield). ESI-MS (Mi-i): 165 calc. for 09H12N20: 164.2.

Statistics shows that 2-Ethoxybenzonitrile is playing an increasingly important role. we look forward to future research findings about 6609-57-0.

Reference:
Patent; FUNDACION PARA LA INVESTIGACION MEDICA APLICADA; CUADRADO TEJEDOR, Maria Del Mar; FRANCO FERNANDEZ, Rafael; GARCIA OSTA, Ana Maria; OYARZABAL SANTAMARINA, Julen; RABAL GRACIA, Maria Obdulia; WO2014/131855; (2014); A1;,
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Electric Literature of 5414-21-1,Some common heterocyclic compound, 5414-21-1, name is 5-Bromovaleronitrile, molecular formula is C5H8BrN, 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 5-hydroxy-7-((2-methyl-[l,r-biphenyl]-3-yl)methoxy)-2,3- cli hydro- 1 /7-indene-4-carbaldehyde (0.50 g, 1.39 mmol) in DMF (10 mL), potassium carbonate (0.288 g, 2.08 mmol) and 5-bromopentanenitrile (0.25 g, 1.53 mmol) were added and stirred the mixture at room temperature for 5 h. After completion, the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (3 x 30 mL). The combined organic layer was dried over sodium sulfate and concentrated. The resulting crude was purified by flash chromatography (silica gel, 12 g cartridge) using 20% EtOAc in hexanes as eluent to obtain 5-((4-formyl-7-((2-methyl-[l,l’-biphenyl]-3-yl)methoxy)- 2,3-dihydro- lH-inden-5-yl)oxy)pentanenitrile (Yield: 0.425 g, 69%) as white solid. LCMS (ES) m/z = 440.51 [M+H]+; NMR (400 MHz, DMSO-d6) d ppm: 1.74-1.80 (m, 2H), 1.86-1.90 (m, 2H), 1.97-2.01 (m, 2H), 2.21 (s, 3H), 2.59 (m, 2H), 2.69 (m, 2H), 3.11 (m, 2H), 4.20 (m, 2H), 5.31 (s, 2H), 6.79 (s, 1H), 7.22 (d, 7 = 7.6 Hz, 1H), 7.28-7.40 (m, 4H), 7.44-7.48 (m, 3H), 10.34 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromovaleronitrile, its application will become more common.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VENKATESHAPPA, Chandregowda; D A, Jeyaraj; PENDYALA, Muralidhar; SIVANANDHAN, Dhanalakshmi; RAJAGOPAL, Sridharan; (233 pag.)WO2019/175897; (2019); A1;,
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Synthetic Route of 1953-99-7,Some common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, molecular formula is C8Cl4N2, 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.

3,4,5,6-tetrachlorophthalonitrile of 6 g (3 eq), KF of 1.8 g (3.1 eq), CaCO3 of 0.5 g (0.5 eq) and 1,2 ethanol of 2.5 g (4 eq) are put in acetone of about 30 ml to about 50 ml (30 eq), and reaction proceeds at room temperature overnight. When the completion of the reaction is verified by thin later chromatography (TLC), work-up is carried out. Subsequently, a resultant product is separated and purified by column chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, its application will become more common.

Reference:
Patent; Samsung Display Co., Ltd.; Kim, Hyunjin; Kang, Sunwoo; Lee, Daewon; Huh, Chul; (14 pag.)US2016/327709; (2016); A1;,
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Synthetic Route of 2469-99-0, The chemical industry reduces the impact on the environment during synthesis 2469-99-0, name is 3-Oxobutanenitrile, I believe this compound will play a more active role in future production and life.

Under nitrogen atmosphere, to a 500 mL of round bottom flask were added 2-cyanoacetone (8 g, 0.096mol) and 200 mL of anhydrous ethanol. 2-cyanoacetone was dissolved with stirring at room temperature. Methylhydrazine (4.43 g, 0.096 mol) was added to obtain a resultant mixture. The mixture was slowly warmed and refluxed. After reacting for 3 hr, the solvent was rotary-evaporated to obtain a product as oil. The product was purified by column chromatography to give 4.2 g of the title compound. MS (ESI): m/z 112 (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, 3-Oxobutanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hande Starlake Bioscience Co., Ltd.; Hande Pharma Limited; LI, Chenxi; SHEN, Weisheng; FANG, Yang; LE, Xiaoyong; EP2578587; (2013); A1;,
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Synthetic Route of 6621-59-6,Some common heterocyclic compound, 6621-59-6, name is 6-Bromohexanenitrile, molecular formula is C6H10BrN, 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 2 (200mg, 0.34mmol), 6-bromohexanenitrile (180mg, 1.0mmol) and powdered NaH (95%; 17mg, 0.67mmol) in dry DMF (2.0mL) was stirred at room temperature under nitrogen for 2.5h. Saturated Na2CO3 buffer (6mL) was added, and the mixture extracted with ethyl acetate (25mL). The organic layer was washed with buffer (4×5mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using cyclohexane: ethyl acetate (1:1) containing 1% Et3N to give 133mg (57%) of 6 as a white foam: 1H NMR (CDCl3): delta 7.83 (d, J=7.2Hz, 2H, H-2?, H-6?), 7.38 (d, J=7.8Hz, 2H, H-3?, H-5?), 6.69 (d, J=8.1Hz, 1H, H-1), 6.54 (d, J=8.1Hz, 1H, H-2), 4.35 (s, 1H, H-5), 4.05-3.85 (m, 1H, H-1?), 3.80-3.57 (m, 1H, H-1?), 3.05 (d, J=6.3Hz, 1H, H-9), 3.03 (d, J=12Hz, 1H, H-10), 2.98-2.79 (m, 1H, H-8), 2.69 (dd, J=11.7Hz, J=4.8Hz, 1H, H-16), 2.52 (s, 3H, H-7?), 2.40 (t, J=7.2Hz, 2H, H-5?), 2.32-2.17 (m, 4H, H-10, H-16, H-22), 2.15-2.00 (m, 1H, H-15), 1.98-1.50 (m, 9H, H-7, H-15, H-18, H-2?, H-4?), 1.43 (s, 3H, H-21), 1.33-1.28 (m, 2H, H-3?), 1.23 (s, 3H, H-20), 1.18-1.00 (m, 2H, H-8, H-17), 0.93-0.79 (m, 1H, H-23), 0.78-0.62 (m, 1H, H-17), 0.61-0.46 (m, 2H, H-24, H-25), 0.2-0.07 (m, 2H, H-24, H-25); HRMS m/z calcd for [M+H]+ 661.3306, found 661.3328; Anal. Calcd for C38H48N2O6S: C, 69.06; H, 7.32; N, 4.24; found: C, 69.32; H, 7.20; N, 4.34.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromohexanenitrile, its application will become more common.

Reference:
Article; Srivastava, Shefali; Fergason-Cantrell, Emily A.; Nahas, Roger I.; Lever, John R.; Tetrahedron; vol. 72; 40; (2016); p. 6127 – 6135;,
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Adding a certain compound to certain chemical reactions, such as: 1122-85-6, name is Phenyl Cyanate, 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 1122-85-6, Quality Control of Phenyl Cyanate

EXAMPLE 4 Preparation of 4-(p-Chlorophenyl)-4-methyl-2-pentynenitrile STR15 A solution of 1,1-dibromo-3-(p-chlorophenyl)-3-methyl-1-butene (38.5 g, 0.113 mol) in tetrahydrofuran is treated with n-butyllithium (0.25 mol, 100 mL of a 2.5M solution in hexane) under nitrogen over 45 minutes while maintaining the temperature below -65 C., stirred overnight at dry ice/acetone bath temperature, treated dropwise with a solution of phenyl cyanate (14.89 g, 0.125 mol) in tetrahydrofuran over 30 minutes at -65 C. to -70 C., allowed to warm to 10 C., and diluted with ethyl acetate and 5% sodium hydroxide solution. The resultant mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with 5% sodium hydroxide solution and water, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. The residue is distilled to give the title product as an oil (18.7 g, bp 110-113 C./0.9 mm Hg, 80.7% yield) Using essentially the same procedure, but substituting 1-(2,2-dibromovinyl)-1-(p-chlorophenyl)-cyclopropane for 1,1-dibromo-3-(p-chlorophenyl)-3-methyl-1-butene, 3-[1-(p-chlorophenyl)cyclopropyl]-2-propyne-1-carbonitrile is obtained as a yellow solid, mp 62-64 C.

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; American Cyanamid Company; US5849958; (1998); A;,
Nitrile – Wikipedia,
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