Tag: M.W=200-300

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. Recommanded Product: Diphenyl N-cyanocarbonimidate

A solution of 4-aminopidine (0.612 g, 6.5 mmol), diphenyl N-cyanocarbonimidate (1.540 g, 6.5 mmol) and triethylamine (1.0 mL, 6.5 mmol) in acetonitrile (15 mL) was stirred at 80 C for 2h and illowed to stir at room temperature for 12 h. The reactionmixture was concentrated under reduced pressure to give a residue. The residue was diluted with ethyl acetate, washed with water. The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography on silica gel (methanoll dichloromethane = 10/90) to give titled compound (0.700 g, 47 %) as green thickmass.LCMS: mlz 239.10 [M+H] .

The synthetic route of Diphenyl N-cyanocarbonimidate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; PANIGRAHI, Sunil Kumar; WO2014/111871; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 499983-13-0,Some common heterocyclic compound, 499983-13-0, name is 4-Bromo-3-fluorophenylacetonitrile, molecular formula is C8H5BrFN, 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.

Example 3Preparation of 4-bromo-3-fluorophenylcyclopropanenitrile (V)A solution of 4-bromo-3-fluorophenylacetonitrile (1 g, 4.6 mmoles) in toluene (4 ml) is mixed with 0.6 ml (7 mmoles) of 1,2-dibromoethane, a 50% NaOH aqueous solution (4 ml), and tetrabutylammonium bromide (0.32 g, 1 mmoles). The mixture is kept under stirring at room temperature for 4 hours, then diluted with water and extracted with ethyl acetate. The organic phase is recovered, and the solvent is eliminated under vacuum to give a brown solid, which is subjected to silica gel chromatography purification, to afford an orange to yellow product in the solid form (1 g, yield 90%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-3-fluorophenylacetonitrile, its application will become more common.

Reference:
Patent; Chiesi Farmaceutici S.p.A.; US2011/39934; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 1503-49-7, The chemical industry reduces the impact on the environment during synthesis 1503-49-7, name is 4-Benzoylbenzonitrile, I believe this compound will play a more active role in future production and life.

General procedure: 2-Furonitrile 1m (186 mg, 2 mmol), NaN3 (260 mg, 4 mmol), BiCl3 (126 mg, 0.4 mmol), and 8 mL of a 3:1 isopropanol/water mixture were added to a 30-mL Pyrex microwave vessel, which was then capped. The microwave vessel was then placed in a Milestone Start Synth microwave reactor. The reaction was magnetically stirred and heated for 1 h at 150C. The reaction was monitored by thin-layer chromatography (TLC) using an ether/hexane mixture (typically 50/50) for development. The reaction mixture was then diluted with saturated aqueous sodium bicarbonate (20 mL) and was hed with ethyl acetate (2¡Á15 mL). The aqueous sodium bicarbonate layer was cooled with ice and acidified to a pH of 2 or less with concentrated hydrochloric acid, which was added dropwise. The precipitate formed was extracted with ethyl acetate (3¡Á15 mL). The combined organic layers were dried with anhydrous sodium sulfate and decanted into a tared round-bottom flask. The organic layer was concentrated under reduced pressure by rotary evaporation at 40C and then under high vacuum. The tetrazole product was recrystallized from ethyl acetate and hexane.

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

Reference:
Article; Coca, Adiel; Feinn, Liana; Dudley, Joshua; Synthetic Communications; vol. 45; 8; (2015); p. 1023 – 1030;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 52133-67-2, A common heterocyclic compound, 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate, molecular formula is C11H19NO4, 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 sodium ethoxide (210 mL, 563 mmol; 21 percent in EtOH) in absolute EtOH (290 mL) were added ethyl-2-cyano-4,4-diethoxybutanoate (45 g, 281 mmol) and 2,2- dimethyl-propionamidine (59 g, 256 mmol) and heated to reflux for 12 h. The mixture was concentrated, the residue was diluted with water (100 mL) and acidified (pH 6-7) with aqueous 2N HC1 solution. The precipitate was filtered, dried under vacuum and dissolved in EtOH (100 mL). H2S04 (10 mL) was added at 0 ¡ãC and the mixture was heated to reflux for 2 h. After cooling to 25 ¡ãC the solution was made basic (pH~8-9) with NH3 aq.. The precipitate was filtered and dried under vacuum to yield 2-tert-butyl-l, 7-dihydro-pyrrolo [2,3-d]pyrimidin-4-one (18 g, 47percent) as white solid which was used in the next step without further purification. MS(m/e): 192 (M+H).

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GRETHER, Uwe; KIMBARA, Atsushi; NETTEKOVEN, Matthias; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; WO2014/177527; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 105942-08-3, 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. 105942-08-3 name is 4-Bromo-2-fluorobenzonitrile, 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.

Step 1: Preparation of the starting material: 4-bromo-2-methoxy-benzonitrile. A mixture of 4-bromo-2-fluoro-benzonitrile (15.0 g, 75.0 mmol), methanol (30.4 mL, 350 mmol) and potassium carbonate (31. Ig, 225 mmol) in DMF (150 mL) was stirred under argon at 55 0C overnight. At this point TLC (100percent methylene chloride) revealed no starting material, and the reaction mixture was poured into ether (300 mL) and water (150 mL). The layers were separated, and the organic layer was washed with water (150 mL) and brine (50 mL), dried over Mg2SO4, filtrated, and concentrated under reduced pressure, providing (15.2 g, 95.5percent) of 4-bromo-2- methoxy-benzonitrile as a white solid. 1H-NMR (CDCl3) 7.41 (d, J = 8.1 Hz, IH), 7.16 (dd, J = 8.1, 1,6 Hz, IH), 7.13 (d, J = 1,6 Hz, IH), 3.93 (s, 3H); MS GC-MS (M+ = 211; RT= 6.15 min).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BAYER HEALTHCARE AG; WO2008/25509; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 425379-16-4, These common heterocyclic compound, 425379-16-4, name is 2-Bromo-3-fluorobenzonitrile, 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.

The product of Example 12 step a) (1.00 g, 4.57 mmol) and 2-BROMO- 3-FLUOROBENZONITRILE (0.91 g, 4.57 mmol) were suspended in 1, 2- dimethoxyethane (20 ml) and 2 N sodium carbonate (10 ml) and the mixture degassed with nitrogen for 30 min. TETRAKIS-TRIPHENYLPHOSPHINE palladium (0) (211 mg, 0.18 mmol) was added and the mixture was heated at 80C for 18 h. The mixture was allowed to cool to ambient temperature, DILUTED WITH ETHYL ACETATE (100 ML) AND WASHED WITH 2 N SODIUM HYDROXIDE solution (75 ml), water (50 ml) and brine (50 ml), dried over anhydrous sodium sulfate, filtered and evaporated to give a pale yellow oil. The oil was purified by flash column chromatography on silica eluting with 0-15% ETOAC/ISOHEXANE to give 0.39 g (29%) of the title compound as a colourless oil which solidified on standing: ON (400 MHz, CDCL3) 7.19 (1 H, ddd, J 8.0, 8.0, 1.0), 7.34-7. 38 (1 H, m), 7.44 (1 H, td, J9.0, 1.4), 7.50-7. 56 (1 H, m), 7.61 (1 H, ddd, J7. 8, 1.0, 0.6), 7. 68-7. 72 (1 H, m).

The synthetic route of 425379-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/65388; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C7H3BrFN

5-Bromo-2-fluorobenzonitrile (53) (500 mg, 2.54 mmol) was coupled to phenylboronic acid (335 mg, 2.75 mmol) with Cs2CO3 (1.63 g, 5.00 mmol) in toluene (4 mL) in a microwave at 140 C. for 30 minutes. Water was added and the organics extracted several times with EtOAc, dried (MgSO4), filtered and the solvent concentrated in vacuo. The crude product was purified by Flash Master Jones Chromatography using a 25 g silica cartridge and eluting with 10% EtOAc in heptane to yield the title compound. Yield: 375 mg, 76%; LC-MS 41.63 min; HPLC Purity: 97%; MS (ES+) m/z not detectable (M+H)

The synthetic route of 179897-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTERAND UK LIMITED; US2010/130556; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-5-fluorobenzonitrile

General procedure: To a solution of 5 (500 mg, 2.55 mmol) in 10 mL of DMF was successively added Et3N (1.42 mL, 10.2mmol), 9a (579 mg, 2.55 mmol), CuI (48 mg, 0.25 mmol), and trans-dichlorobis(triphenylphosphine)palladium (177 mg, 0.25 mmol). The resulting solution was warmed to 60 oC, and TBAF 1M in THF (2.8 ml, 2.80mmol) was added dropwise. After 2h at this temperature the mixture was hydrolyzed with 50 mL of H2O and, extracted with AcOEt (4 X 30 mL). The organic layer was washed with saturated NaCl (3 X 30 mL), dry over anhydrous Na2SO4, and concentrated on a rotary evaporator. Purification of the residue by column chromatography (hexane/AcOEt 8/2) yielded 439 mg (64 %) of 1a as an off white solid. 1H NMR (CDCl3), d = 2.67 (s, 3H, CH3); 7.46 (s, 1H, CHAr); 8.00 (t, 1H, J= 1.6 Hz, CHAr); 8.35 (t, 1H, J=1.6 Hz, CHAr); 8.47 (t, 1H, J=1.6 Hz, CHAr). 13C NMR (CDCl3), d = 19.6 (1C, CH3); 84.6 (1C, C?C); 89.1 (1C, C?C); 114.8 (1C, Cq); 116.3 (1C, Cq); 125.5 (1C, CHAr); 126.5 (1C, CHAr); 126.6 (1C, CHAr); 130.4 (1C, CHAr); 135.4 (1C, Cq); 140.1 (1C, CHAr); 148.6 (1C, Cq); 166.9 (1C, Cq). Anal (C13H7N3O2S, HCl) C, H, N.

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; Alagille, David; Dacosta, Herve; Chen, Yelin; Hemstapat, Kamondanai; Rodriguez, Alice; Baldwin, Ronald M.; Conn, Jeffrey P.; Tamagnan, Gilles D.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 11; (2011); p. 3243 – 3247;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 846023-24-3,Some common heterocyclic compound, 846023-24-3, name is 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide, molecular formula is C10H8Cl2N2O2, 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.

Isopropanol (80 ml) was added to the reaction flask, and 2-cyano-N- (2,4-dichloro-5-methoxyphenyl) acetamide (10.0 g) and triethyl orthoformate ( 12.03g).The temperature was raised to 80 C, and a solution of isopropylamine (2.4 g) in isopropyl alcohol (60 ml) was added dropwise.Keep stirring for 24h.The system was cooled to room temperature, centrifuged, the solid was dissolved in dichloromethane (130 ml), and separated by column chromatography (n-hexane / ethyl acetate (v / v) = 3: 1) to obtain an off-white solid impurity (I-iPr). .Yield: 94.7%, purity: 99.9%.

The synthetic route of 846023-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hangzhou China-USA East China Pharmaceutical Co., Ltd.; Wu Yao; Zhou Ting; Jiang Dongdong; Jin Yanfen; Yang Yong; Chen Yu; (16 pag.)CN110372539; (2019); A;,
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. 97165-77-0, name is 3,5-Dibromobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H3Br2N

Compound II – 2 (2.61 g, 10 mmol), compound III (2.06 g, 10 mmol), Pd (OAc)2(0.22 G, 1 mmol), BINAP (2, 2 ‘- bi-phenyl diphenylphosphino – 1, 1’ – binaphthyl, 0.62 g, 1 mmol) and t – BuOK (2.24 g, 20 mmol) is added to the 50 ml dry 1, 2 – dimethoxy ethane (DME), the reaction mixture is stirred under a nitrogen atmosphere overnight, detected in the TLC reaction is completed.The reaction mixture carefully dumped into 200 ml ice water, stirring, for 50 ml ¡Á 3 CH2Cl2Extraction, the combined extraction phase, for sequentially 1% dilute hydrochloric acid and salt is washed with water, dried with anhydrous sodium sulfate. Oil filtration to remove the drying agent, the filtrate on a rotary evaporator to dryness, the residue using silica gel column chromatography purification, to obtain compound IV – 2

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 97165-77-0.

Reference:
Patent; Guangdong Sai Bo Technology Co., Ltd.; Guo Huijun; (8 pag.)CN107903271; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts