Category: nitriles-buliding-blocks

Some common heterocyclic compound, 114344-60-4, name is 2-Amino-3-bromobenzonitrile, molecular formula is C7H5BrN2, 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. name: 2-Amino-3-bromobenzonitrile

3-Bromo-2-[1-(4-methoxybenzyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino]-benzonitrileThe 4-methoxy-1-(4-methoxybenzyl)-1,5-dihydro-pyrrol-2-one (11.19 g, 48.0 mmol), 2-amino-3-bromobenzonitrile (11.83 g, 60.1 mmol), and p-toluene sulfonic acid (8.22 g, 43.2 mmol) were mixed together, ground to fine powder and transferred to a round-bottomed flask. The flask was placed in a preheated 130 C. oil bath and the reaction stirred for 40 minutes. The reaction mixture was removed from the bath, cooled, and dissolved in methylene chloride. The solution was washed with sodium bicarbonate (saturated aqueous solution) and the organic layer dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford a brown solid (19.5 g). The crude material was purified by flash chromatography on silica gel eluting with a gradient of 20 to 40% ethyl acetate in methylene chloride to afford the desired compound (6.58 g, 34%). 1H NMR (300.132 MHz, DMSO) delta 9.10 (s, 1H), 8.07 (dd, J=8.1, 1.3 Hz, 1H), 7.92 (dd, J=7.7, 1.2 Hz, 1H), 7.40 (t, J=8.0 Hz, 1H), 7.15 (dt, J=8.6, 2.3 Hz, 2H), 6.91 (dt, J=8.9, 2.3 Hz, 2H), 4.44-4.37 (m, 3H), 3.88 (s, 2H), 3.74 (s, 3H). MS APCI, m/z=398/400 (M+H). HPLC 1.94 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 114344-60-4, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; US2008/318943; (2008); A1;,
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. 925672-88-4, name is 5-Bromo-2-cyanobenzeneacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 5-Bromo-2-cyanobenzeneacetonitrile

1 ,6-Dibromoisoquinolin-3-amine. 4-Bromo-2-(cyanomethyl)benzonitrile(75 g, 339 mmol) was added to 2,2-dichloroacetic acid (150 mL, 339 mmol). The resulting solution was cooled to 0C in an ice-water bath. HBr (27.5 g, 339 mmol) was bubbled through the cold solution until a yellow precipitate crashed out of solution, resulting in a yellow slurry. HBr was bubbled through the slurry for an additional 5 minutes. The solution was allowed to warm to room temperature over 1 hour. The slurry was then cooled to 0C in an ice-water bath and diethyl ether (200 mL) was added. The mixture was stirred for 20 minutes at 5C. The product was recovered as a yellow solid by filtration (42 g, 41 %). LCMS (API-ES) m/z: 303 (M-^H+).

According to the analysis of related databases, 925672-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; WO2009/11871; (2009); A2;,
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. 6136-93-2, name is 2,2-Diethoxyacetonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C6H11NO2

EXAMPLE II PREPARATION OF 2-ETHYLIDENE-6-METHYL-CIS-3-HEPTENAL A solution of 5.40 g of isobutylacetylene in 50 ml of diethyl ether is treated with 30 ml of 2.2 N n-butyl-lithium in hexane at -20 C, and after several minutes the resulting solution is treated with 8.50 g of diethoxy-acetonitrile and then warmed solwly to room temperature. After about 1.5 hours the dark mixture is cooled and brought to a pH of about 2 with 10% sulfuric acid. The layers are then separated and the organic layer is washed successively with water and saturated aqueous sodium bicarbonate solution and then dried over sodium sulfate. Evaporation of the solvent provides 4.6 g of a dark oil, shown by IR and NMR to contain 1,1-diethoxy-6-methyl-3-heptyn-2-one.

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; International Flavors & Fragrances Inc.; US4107217; (1978); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

185147-07-3, name is 2-Fluoro-3-methylbenzonitrile, 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: C8H6FN

Step 1 K2CO3 (8.18 g, 59.2 mmol) was added to a RT solution of 2-fluoro-3-methylbenzonitrile (4.0 g, 29.6 mmol) and 1H-1,2,3-triazole (1.72 mL, 29.6 mmol) in DMF (80 mL) and the resulting suspension was heated to 120 C. for 4 h. The reaction mixture was cooled to RT and quenched with water before being extracted with EtOAc (3*). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo to give the crude product that was purified by flash chromatography (eluting with a gradient of 33% to 50% EtOAc in hexane) to give 3-methyl-2-(2H-1,2,3-triazol-2-yl)benzonitrile as a white solid. LC-MS B: tR=0.62 min; [M+H]+=185.16.

The synthetic route of 185147-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD.; Bolli, Martin; Boss, Christoph; Brotschi, Christine; Heidmann, Bibia; Sifferlen, Thierry; Williams, Jodi T.; US2015/158855; (2015); A1;,
Nitrile – Wikipedia,
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3939-09-1, name is 2,4-Difluorobenzonitrile, 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. Product Details of 3939-09-1

A solution of 2,4-difluorobenzonitrile (7.07 g, 50.8 mmol) and 3-methyl-1H-1,2,4-triazole (4.22 g, 50.8 mmol) in N,N-dimethylformamide (45 ml) was treated with powdered anhydrous potassium carbonate (10 g) and the resulting mixture was stirred at 22 C. for 18 h. The solid was then filtered and the filtrate was concentrated in vacuo. The residue was diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated. The mixture containing the 2 and 4-triazolyl-benzonitriles was purified by a combination of chromatography on silica gel (elution gradient of ethyl acetate in hexane) and on reversed phase silica gel to give 1.86 g (18% yield) of Intermediate 5 and 0.526 g (5% yield) of Intermediate 6. Intermediate 5 4-Fluoro-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile: White crystals (ethyl acetate/hexanes); mp 117-118 C. 1H NMR (400 MHz, CDCl3) delta: 8.82 (1H, s), 7.84 (1H, dd, J=5.6, 8.6 Hz), 7.62 (1H, dd, J=2.5, 9.1 Hz), 7.24 (1H, m), 2.54 (3H, s). Anal. Calcd for C10H7FN4: C, 59.40; H, 3.49; N, 27.71. found: C, 59.25; H, 3.32; N, 27.81. Intermediate 6 4-fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrile: White crystals (ethyl acetate-hexane); mp 120-121 C. 1H NMR (400 MHz, CDCl3) delta: 8.06 (1H, s), 7.91 (1H, dd, J=5.5, 8.6 Hz), 7.39 (1H, m), 7.30 (1H, dd, J=2.5, 8.1 Hz), 2.56 (3H, s). Anal. Calcd for C10H7FN4: C, 59.4; H, 3.49; N, 27.71. found: C, 59.35; H, 3.70; N, 27.77.

The synthetic route of 3939-09-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/112190; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 21524-39-0, These common heterocyclic compound, 21524-39-0, name is 2,3-Difluorobenzonitrile, 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.

Step A: 2-Azido-5-fluorobenzonitrile (1q): A mixture of NaN3 (1.17 g, 1.8 mmol) and difluorobenzonitrile (0.5 g, 3.6 mmol) in DMA (60 mL) was heated at 100 C. for 30 minutes. The mixture was next diluted with water (300 mL) and ether (300 mL). The organic layer was washed three times with water and brine. The organic layer was dried (MgSO4) and concentrated. The crude product was purified by flash column chromatography using ether:hexane (1:5) as eluent to give the desired product (1q) as white crystals (0.3 g, 53% isolated yield). 1H NMR (400 MHz, CDCl3) delta 7.38-7.31 (m, 2H), 7.27-7.18 (m, 1H).

The synthetic route of 21524-39-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Munson, Mark; Kim, Youngboo; Groneberg, Robert D.; Rizzi, James; Rodriguez, Martha; Kim, Ganghyeok; Vigers, Guy; Rao, Chang; Balachari, Devan; US2004/180896; (2004); A1;,
Nitrile – Wikipedia,
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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. 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, A new synthetic method of this compound is introduced below., Safety of 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile

General procedure: A mixture of an aromatic or heteroaromatic aldehyde(10.00 mmol) and an active methylene compound (10.0mmol) in acetic anhydride (15 mL) was stirred underexclusion of moisture in a water bath at 90C for 8 h.Under consumption of the starting material a deeply colouredsolution was observed and by the time a crystallineprecipitate was formed. After cooling to 0C the precipitatewas filtered off by suction, washed exhaustively withmethanol (100-200 mL) until the filtrate showed thecolour of the desired product in solution and then dried inair at room temperature.The following compounds were so prepared.

The synthetic route of 1080-74-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Heichert, Christoph; Hartmann, Horst; Zeitschrift fur Naturforschung, B: Chemical Sciences; vol. 71; 6; (2016); p. 651 – 658;,
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Synthetic Route of 20249-16-5, 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. 20249-16-5 name is 3-Oxocyclobutanecarbonitrile, 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.

A solution of 3-oxocyclobutane-1-carbonitrile* (CAS: 20249-16-5, 14.5 g, 152 mmol) in THF (250 mL) was added to a mixture of (EtO)2P(O)CH2CN (31.1 g, 175 mmol), LiBr (19.9 g, 229 mmol) and TEA (30.9 g, 305 mmol) in THF (300 mL) at about 25 C. After about 16 hrs, the mixture was filtered and the filtrate was concentrated. The residue was purified by chromatography to afford the title compound as a light yellow oil (16.01 g, 89%).1H NMR (400 MHz, CD3CN) delta: 5.38 (s, 1H), 3.30-3.43 (m, 2H), 3.16-3.30 (m, 3H).LCMS m/z=119.1 [MH]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Oxocyclobutanecarbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc.; BROWN, Matthew Frank; DERMENCI, Alpay; FENSOME, Andrew; GERSTENBERGER, Brian Stephen; HAYWARD, Matthew Merrill; OWEN, Dafydd Rhys; WRIGHT, Stephen Wayne; XING, Li Huang; YANG, Xiaojing; (67 pag.)US2017/240552; (2017); A1;,
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Electric Literature of 654-70-6,Some common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, molecular formula is C8H5F3N2, 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.

20L three-necked flask by adding 5.94L water, 270mL thiophosgene, the temperature control in the 20 ~ 30C ,457 g of 4-amino-2- (trifluoromethyl) benzonitrile was added portionwise under stirring,After the addition, the reaction was continued for 1 h. The reaction was complete by TLC method, extracted with dichloromethane (1 L x 3)The organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated, added with petroleum ether beating,Through liquid nitrogen crystallization, filtration, drying, the product 500g, yield 89.3%.

The synthetic route of 654-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai DingYa Pharmaceutical Chemicals Co.,Ltd; Ruan, Shiwen; Yan, Haiyan; Xia, Hongfei; Xu, LiPing; (6 pag.)CN104016924; (2016); B;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 555-21-5, name is 4-Nitrophenylacetonitrile, 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 555-21-5, Formula: C8H6N2O2

A mixture of (4-nitrorhohenyl)-acetonitrile (4.33 g5 27 mmol), NaOH (3.24 g, 81 mmol), iodomethane (5.5 mL, 88 mmol), and tetrabutylammonium iodide (0.56 g, 1.5 mmol) was stirred in water (35 mL) and dichloromethane (35 mL) for 24 hrs at about 25C, extracted with dichloromethane, dried (MgSO4), and concentrated. The residue was dissolved in diethyl ether, filtered through Celite, concentrated, re-filtered through Celite with dichloromethane, and concentrated. This product was dissolved in ethyl acetate, treated with SnCl2 (20 g, 106 mmol). The mixture was stirred overnight at 7O0C, concentrated, and partitioned between ethyl acetate and IN aqueous NaOH. The organic layer was isolated, EPO washed with brine, dried (Na2SO4), and concentrated to afford the title compound (3.69 g). 1H NMR (300 MHz, CDCl3) delta 7.24 (d, 2H), 6.68 (d, 2H), 1.68 (s, 6H).

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

Reference:
Patent; ABBOTT LABORATORIES; WO2006/65646; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts