Tag: M.W=200-300

These common heterocyclic compound, 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, 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. 75344-77-3

Step 1: 4-Bromo-3,5-dimethylbenzonitrile (0.5 g, 2.38 mmol) was dissolved in THF (12 ml). The solution was cooled in a dry ice/diethyl ether bath. N-butyllithium (1.05 ml 2.50M solution in hexanes, 2.62 mmol) was added slowly over 30 m. Dry N,Ndimethylformamide (0,26 ml, 3.3 mmol) was then added slowly and the reaction allowed to warm slowly. After 1 h the reaction appeared complete (LC/MS, TLC) and by 2 h with the temperature at -30 C, the reaction was neutralized by addition of an aqueous saturated sodium chloride solution. The mixture was taken up in ethyl acetate and water, the phaseswere separated, the aqueous phase was extracted once more with ethyl acetate, and the combined organics were washed with more saturated sodium chloride solution. After drying over sodium sulfate, flhration and evaporation, the residue was purified by silica gel chromatography (ethyl acetate/hexanes gradient) to give 4-formyl-3,5 -dimethylbenzonitrile as a white solid (0.18 g, 47%).

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 75344-77-3.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; LI, Zhe; ZANCANELLA, Manuel; YU, Chul; SETTI, Lina; SHAM, Hing; XU, Qing; YEE, Calvin; YU, Ming; (402 pag.)WO2016/201052; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, molecular formula is C8Cl4N2, 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. 1953-99-7.

[formula c] 0.0375 mol, [formula a]0.0125 mol, zinc bromide 0.015 mol and1,8- diazabicyclo [5.4.0] undec -7-ene 0.05 mol were added to amylalcohol 66 g and stirred. The reaction temperature was raised to 130 and the reaction was carried out for 8 hours. After thereaction was complete, the reaction solution was cooled down and concentratedunder reduced pressure to remove the solvent by 2/3. The addition of methanolwas followed by to crystalize the solution. The crystals were filtered underreduce pressure and was dispersedly filtered in the mixed solution of methanol50g for 1 hour. The crystals were suction filtered and vacuum dried at 60 to obtain phthalocyanine compound 7.9g.

The synthetic route of 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyung-In Synthetic Corporation; Park, Soon Hyeon; Kim, Jeong Ki; Kim, Jeong Rok; Lee, Yun Ah; Lee, Do kyeong; Lee, Min Jeong; Lee, Hui Jae; (16 pag.)KR2016/7024; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

79463-77-7,Some common heterocyclic compound, 79463-77-7, name is Diphenyl N-cyanocarbonimidate, molecular formula is C14H10N2O2, 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 solution of (R)-3-tert-butoxycarbonylaminopipiridine (154.0 g, 0.769 mol) in iPrOH (3.0 L) was added diphenyl cyanocarbonimidate (183.2 g, 0.769 mol). The mixture was stirred at room temperature for 2.5 h. To the reaction mixture was added glycine ethyl ester¡¤hydrochloride (536.7 g, 3.85 mol) at 0 C, and the mixture was stirred at 80 C for 6 h. After cooling to room temperature, the reaction mixture was diluted with AcOEt (1.4 L) and the precipitate was removed by filtration through a Celite pad. The filtrate was concentrated in vacuo, and the residue was diluted with 5% sodium carbonate solution and extracted with CHCl3 three times. The combined organic layers were dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica-gel column chromatography to give 7 (249.2 g, yield 92%) as a pale yellow oil. 1H NMR (300 MHz, CDCl3) delta 5.68 (br s, 1H), 4.66 (br s, 1H), 4.28-4.19 (m, 4H), 3.81-3.34 (m, 5H), 2.05-1.51 (m, 4H), 1.45 (s, 9H), 1.30 (t, J=7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3) delta 169.6, 160.0, 155.5, 117.1, 80.1, 61.8, 51.2, 47.3, 45.4, 44.6, 29.8, 28.3, 22.8, 14.1; HRMS (ESI) [M+H]+ calcd for C16H28N5O4 354.2136, found 354.2128; IR (ATR): 1743, 1685, 1575, 1531, 1440, 1390, 1365, 1309, 1243, 1197, 1162, 1051, 1031, 1018 cm-1.

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

Reference:
Article; Ikuma, Yohei; Nakahira, Hiroyuki; Tetrahedron; vol. 67; 49; (2011); p. 9509 – 9517;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 114897-91-5, name is 2-(4-Bromo-2-fluorophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., 114897-91-5

MeOH (16MMOL, 0.81 ml), TMSCI (20mmol, 2. 13g) and (4-bromo-2-fluorophenyl) acetonitrile (10MMOL, 2. 13g) were sequentially added to a dry flask under a nitrogen atmosphere at room temperature. The reaction mixture was heated at 50 C for 4 hours. After being cooled to room temperature, water (20MMOL, 0. 36MOI) was added to the mixture, followed by the addition of NA2CO3 (10mmol, 1. 06g) and CH2Cl2 (10ml). Drying over MGSO4 and concentrating at low pressure afforded product (0.85 g, 35% YIELD). H NMR (300 MHz, CDC13) No. : 3.57 (s, 2 H), 3.65 (s, 3H), 7.08 (t, J=8.3 Hz, 1H), 7.16-7. 21 (m, 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; PFIZER INC.; WO2004/74270; (2004); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

1813-33-8, The chemical industry reduces the impact on the environment during synthesis 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol) and appropriate thiol (RSH, 3.00 mmol),18-crown-6-ether (cat.) and potassium carbonate (2.00 mmol)were dissolved in acetonitrile (3 ml). The mixture was refluxedfor 12 h and then cooled to ambient temperature. The mixturewas quenched by adding water and extracted with EtOAc.Extracted organic compound was dried over MgSO4, filtered, andconcentrated in vacuo. The residue was purified by flash columnchromatography on silica gel using EtOAc/hexane (1:4) eluantcondition. (RSH = CH3CO2(CH2)2SH for 42).

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

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

114897-91-5, A common heterocyclic compound, 114897-91-5, name is 2-(4-Bromo-2-fluorophenyl)acetonitrile, molecular formula is C8H5BrFN, 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.

(11-2) According to a method similar to Example (8-1), from (4-bromo-2-fluorophenyl)acetonitrile (3.0 g, 14 mmol) obtained in Example (11-1) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (3.45 g, 14 mmol), (3-fluoro-4′-hydroxy-1,1′-biphenyl-4-yl)acetonitrile was obtained as a colorless solid (2.9 g, yield: 91%). 1H-NMR (400MHz, MeOH-d4): delta 7.50-7.34 (5H, m), 6.87 (2H, d, J=8.8Hz), 3.92 (2H, s).

The synthetic route of 114897-91-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP1806332; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

17216-62-5, 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. 17216-62-5, name is Diethyl 2-(2-cyanoethyl)malonate, A new synthetic method of this compound is introduced below.

EXAMPLE 9 1,4,8,11-Tetraaza-6-(2-cyanoethyl)-5,7-dioxoundecane, 8 Diethyl 2-(2-cyanoethyl)malonate 7 (5.0 g, 23.5 mmole–Aldrich Chemical Company) was added dropwise over a one hour period to a stirred portion of freshly distilled ethylene diamine (15 g, 0.25 mole) which was maintained under nitrogen at O C. The stirred solution was allowed to warm to room temperature (25 C.) and stirring was continued over a four day period. At this point, the excess ethylene diamine was removed in vacuo with care to avoid heating over 40 C. The crude clear oil which resulted was subjected to flash chromatography using Solvent System 3 as the eluent to give 2.3 g (8.81 mmole) of 1,4,8,11-tetraaza-6-(2-cyanoethyl)-5,7-dioxoundecane as a clear viscous oil in 37 percent yield (Rf =0.39/Solvent System 3): 1 H NMR (CDCl3) delta 7.59 (t, 2H, amide H), 3.29 (m, 5H, methine H and alpha-amido CH2), 2.82 (dt, 4H), beta-amido CH2) 2.48 (t, 2H, alpha-nitrile CH2) 2.21 (q, 2H, beta-nitrile CH2),1.39 (s, 4H, amino NH); 13 C NMR (CDCl3) delta 169.6 (amide carbonyl), 118.9 (nitrile), 52.9, 42.3, 41.2, 27.1, 15.4.

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; The Dow Chemical Company; US5489425; (1996); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding some certain compound to certain chemical reactions, such as: 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, 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 179898-34-1. 179898-34-1

Example 15 1,1-Dimethylethyl[(3-bromo-5-fluorophenyl)methyl]carbamate NaBH4 (1.99 g, 52.5 mmol) was cautiously added to a solution of NiCl2 (1.36 g, 10.5 mmol), Boc2O (4.58 g, 21.0 mmol) and 3-bromo-5-fluorobenzonitrile (2.10 g, 10.5 mmol) in absolute ethanol (30 mL) at 0 C. (vigorous reaction with the formation of a black precipitate). Once the reaction had subsided the mixture was left to stir at room temperature for 30 min. Ethanol was removed under reduced pressure and the precipitate was dissolved in EtOAc, filtered and repeatedly washed with EtOAc. The combined organic phases were washed with saturated NaHCO3, and dried (Na2SO4). After removing the solvent, the product, was purified by flash column chomatography to yield 1,1-dimethylethyl[(3-bromo-5-fluorophenyl)methyl]carbamate (2.20 g, 69%). 1H NMR (400 MHz, CDCl3) delta 1.46 (S, 9H), 4.28-4.32 (m, 2H), 4.87 (br, 1H), 6.93-7.29 (m, 3H); 13C NMR (100 MHz, CDCl3) delta 20.3, 43.6, 44.1, 79.7, 80.0, 113.0, 114.0, 117.7, 122.5, 126.0, 123.0, 141.7, 155.9, 161.5, 164.0.

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 3-Bromo-5-fluorobenzonitrile.

Reference:
Patent; Glaxo Group Limited; US2009/203677; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 328-87-0 as follows. 328-87-0

Step A: Preparation of 2-(p-methoxybenzylthio)-5-trifluoromethylbenzoic acid A solution of p-methoxybenzylmercaptan (20.0 g, 0.13 mol) and sodium methoxide (7.0 g) in N,N-dimethylformamide (55 ml) was added dropwise with stirring under a nitrogen atmosphere to a solution of 4-chloro-3-cyanobenzotrifluoride (26.7 g, 0.13 mol) in N,N-dimethylformamide (35 ml) cooled in an ice bath. After stirring for 2 hours at room temperature, the reaction mixture was poured into ice-water and extracted several times with dichloromethane. The combined organic extracts were dried (sodium sulfate) and evaporated to afford in essentially quantitative yield, 2-(4′-methoxybenzylthio)-5-trifluoromethylbenzonitrile as an oil; 60 MHZ NMR spectrum in chloroform-d was in accord with the desired structure.

According to the analysis of related databases, 328-87-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck & Co., Inc.; US4663344; (1987); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 79463-77-7, name is Diphenyl N-cyanocarbonimidate, 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. 79463-77-7

To a stirred suspension of rac-allyl [3-(3,4-dichlorophenyl)-4,5-dihydro-lH-pyrazol-4-yl]carbamate (intermediate 7), 50.0 g (0.159 mol) in 2-propanol (860 mL) was added diphenyl N- cyanocarbonimidate, 38.0 g (0.159 mol). The reaction mixture was heated to reflux at which point the suspension dissolved into solution after a further 10 minutes at reflux a white precipitate formed. The reaction mixture was stirred at reflux for a further 1 hour before allowing to slowly cool to room temperature overnight. The precipitate was filtered, washing with diethyl ether (2 x 250 mL) and the resulting white solid was allowed to dry to yield rac-phenyl 4-{ [(allyloxy)carbonyl]amino}-N-cyano- 3-(3,4-dichlorophenyl)-4,5-dihydro-lH-pyrazole-l-carboximidate as a white solid, 48.6 g (67 %). NMR (400 MHz, DMSO-d6): delta [ppm] = 4.13 (apparent d, IH), 4.47 (m, 3H), 5.14 (dd, 2H), 5.51- 5.63 (m, IH), 5.79-5.90 (m, IH), 7.23 (d, 2H), 7.30 (t, IH), 7.45 (t, 2H), 7.79 (br m, 2H), 7.97 (br s, IH), 8.19 (d, IH). LCMS (method 3): Rt 1.75 min MS (ESI): [M + H]+ = 458.0

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 79463-77-7.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; MOWAT, Jeffrey Stuart; STELLFELD, Timo; STRESEMANN, Carlo; HILLIG, Roman; KOeHR, Silke; STOeCKIGT, Detlef; WEISKE, Joerg; BRUMBY, Thomas; BARACK, Naomi; CHRIST, Clara; TER LAAK, Antonius; BADOCK, Volker; CRAMPTON, Rosemary Helen; STEFANUTI, Ian; (186 pag.)WO2016/91845; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts