Month: November 2020

Some common heterocyclic compound, 17420-30-3, name is 2-Amino-5-nitrobenzonitrile, molecular formula is C7H5N3O2, 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. 17420-30-3

a. 2,5-Diaminobenzonitrile To a solution of 80 grams (0.356 mole) of stannous chloride dihydrate in 200 ml. of concentrated hydrochloric acid is added in portions over the course of about 5 minutes, 16.314 grams (0.1 mole) of 5-nitroanthranilonitrile. Water cooling is used and the internal temperature rises to about 50. Stirring is continued for 4 hours and the mixture is allowed to stand overnight. The reaction mixture is cooled to 5 in an ice-bath and a cold 50% solution of sodium hydroxide added until the mixture is strongly basic. The mixture is extracted with methylene chloride. The methylene chloride extracts are washed with water and the solvent removed by distillation. There is obtained 11.51 grams (86.5%) of material melting at 85-87. Recrystallization from benzene-skellysolve B gives material melting at 86-7. The infrared spectrum is in agreement.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17420-30-3, its application will become more common.

Reference:
Patent; The Upjohn Company; US4067995; (1978); A;,
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 123-06-8 as follows. 123-06-8

In tert-butylhydrazine hydrochloride (8.67 g, 69.6 mmol)Was added triethylamine (9.7 mL, 69.6 mmol)After adding anhydrous ethanol (460 mL), the mixture was stirred and dissolved at room temperature,Ethoxymethylenemalononitrile (8.5 g, 69.6 mmol) was added in small portions.After heating the solution to reflux for 3 hours,After cooling, the solvent was evaporated to give an orange solid.And extracted with ethyl acetate (0.5 L) and water (0.25 L)After drying by adding magnesium sulfate,The organic layer was evaporated to give an orange-yellow solid.The resulting solid was continuously washed with a 10% ethyl acetate in cyclohexane solution to give a crystalline solid5-amino-1-tert-butyl hydrogen – pyrazol-4-cyano 9.54g(Yield: 83%).

According to the analysis of related databases, 123-06-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; West China Hospital, Sichuan University; He, Yang; Li, Weimin; Zhang, Li; (20 pag.)CN106008527; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A common compound: 939-80-0, name is 4-Chloro-3-nitrobenzonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 939-80-0

TO a mixture of 4-chloro-3-nitro-benzonitrile (24.0 g, 131 mmol) and 3,5-dichloro-phenol (32.0 g, 197 mmol) in dry THF (150 ml) was added NaH (6.84 g, 171 mmol) in portions and the mixture was refluxed for 1 hour. After cooled to room temperature, the solvent was evaporated, and 100 ml of ice water and 20 ml of 4N NAOH aq. were added to the residue. The precipitate was collected by filtration, washed with 0.5 N NAOH aq. and water, dried in vacuo to give the 5-cyano-2- (3, 5-dichlorophenoxy) nitrobenzene (40.0 g, 98.4%) as slight yellow solid.

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, 939-80-0, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER HEALTHCARE AG; WO2004/84898; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A common compound: 194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 194853-86-6

Procedure for synthesis of cyano-nilutamide (1) (Cogan, P. S.; Koch, T. H. Rational Design and Synthesis of Androgen Receptor-Targeted Nonsteroidal Anti-Androgen Ligands for the Tumor-Specific Delivery of a Doxorubicin-Formaldehyde Conjugate. J Med. Chem. 2003, 46, 5258-5270) 4-Fluoro-2-(trifluoromethyl)benzonitrile (4.02 g, 21.3 mmol) was added to Hydantoin (13.6 g, 106.3 mmol) and Potassium Carbonate (4.40 g, 31.9 mmol) in 60 mL DMF and stirred at 45C under argon for 48 hours. Reaction mixture was then diluted in ethyl acetate and washed three times with water. Organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. Column chromatography (eluent 30: 1 DCM/Methanol) gave 1 as a white solid (4.62 g, 74%). 1H NMR (400 MHz, (CD3)2-CO) delta 1.54 (6H, s), 7.80 (1H, s), 8.13 (1H, dd, J = 1.8 Hz, J = 8.4 Hz), 8.20 (1H, d, J = 8.4 Hz), 8.26 (1H, d, J = 1.8 Hz)

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, 194853-86-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GEORGIA TECH RESEARCH CORPORATION; OYELERE, Adegboyega; GRYDER, Berkley; WO2012/50868; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

2042-37-7, Adding some certain compound to certain chemical reactions, such as: 2042-37-7, name is 2-Bromobenzonitrile, 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 2042-37-7.

K3PO4 (212 mg, 1 mmol),aryl halides (0.5mmol) and phenylboronicacid (0.75 mmol) were added successively into a dried Schlenk tubewith a magnetic bar under nitrogen. Then a N,N-dimethylacetamide (DMA 0.05 mL) solution of tetraphosphine TPPDA (0.0005 mmol) andPdCl2 (0.0005 mmol), which was reacted at 100 C for 1 h prior to use,was added into the mixture. Afterwards, o-xylene (3 ml) was addedwith syringe. After being stirred for the required time in the preset con-ditions, the reaction mixture was cooled to room temperature. The mix-ture solution was extracted with ethyl acetate (3 5 mL). Combinedorganic phase was washed with brine (3 5 mL) and dried over anhy-drous MgSO4. The dried solution was ltered and puried by silica gelchromatography (petroleum ether 60-90 C) to give a correspondingproduct. Reaction condition: aryl halides 0.5 mmol, phenylboronic acid 0.75 mmol, K3PO4 1.0mmol, o-xylene 3 mL, catalyst PdCl2/TPPDA = 1/1, 90 C, under nitrogen, GC yields.

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 2042-37-7.

Reference:
Article; Guo, Fei-Chen; Zhou, Rong; Jiang, Zhi-Jie; Wang, Wei; Fu, Hai-Yan; Zheng, Xue-Li; Chen, Hua; Li, Rui-Xiang; Catalysis Communications; vol. 66; (2015); p. 87 – 90;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

127946-77-4, A common heterocyclic compound, 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, molecular formula is C4H7ClN2, 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.

Boc-L-phenylalanine (1) (3.77 mmol, 1 Eq), HATU (1.3 Eq) and 1-Amino-1-cyclopropanecarbonitrile hydrochloride (2) (1.3 Eq.) in DMF(5 mL), under argon atmosphere. The resulting solution was stirred at room temperature for 16 h. The reaction mixture was diluted with ethylacetate (10 mL) and washed with a saturated NaHCO3 solution(3¡Á20 mL) and brine (3¡Á20 mL). The organic phase was dried over MgSO4 and evaporated to give a crude residue that was purified by chromatographic column on Flash Silica using ethyl acetate: n-hexane(7:3) as the mobile phase to give a white solid with a good yield.Yield 92%. White solid. Rf=0.9 (Ethyl Acetate: n-Hexane; 7:3). MP.146-147 C. 1H NMR (500 MHz, CDCl3) delta 7.27-7.04 (m, 5H), 4.58 (m,1H), 3.19 (dd, J=13.8, 5.0 Hz, 1H), 2.88 (dd, J=9.5, 5.0 Hz, 1H),1.31 (s, 9H), 1.25 (m, 2H), 1.04 (m, 2H).13C NMR. (125 MHz, CDCl3) delta 142.88, 131.04, 127.69, 126.21,120.81, 107.59, 37.36

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

Reference:
Article; Cianni, Lorenzo; Sartori, Geraldo; Rosini, Fabiana; De Vita, Daniela; Pires, Gabriel; Lopes, Bianca Rebelo; Leitao, Andrei; Burtoloso, Antonio C.B.; Montanari, Carlos A.; Bioorganic Chemistry; vol. 79; (2018); p. 285 – 292;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

145689-34-5, Adding a certain compound to certain chemical reactions, such as: 145689-34-5, name is 2-(2,3-Difluorophenyl)acetonitrile, 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 145689-34-5.

To a solution of 2,3-difluorophenylacetonitrile (5.00 g, 32.7 mmol) in dry tetrahydrofuran (70mL) sodium hydride (1.70 g, 42.4 mmol; 60% in mineral oil) was added portion wise at 000.Reaction mixture was allowed to warm to room temperature. After stirring for 1 h diethylcarbonate (4.63 g, 39.2 mmol, 4.8 mL) was slowly added. After stirring for 18 h. the reactionmixture was quenched by the addition of hydrochloric acid (1.0 M; 200 mL) and was extracted with ethyl acetate (2×150 mL). The combined organic layers were washed with brine, dried with sodium sulfate and concentrated in vacuo. Purification by flash column chromatography (Method L7; 120 g; heptane, 2%-15% ethyl acetate) afforded 6.96 g (30.2 mmol; 92% oftheory) of the title compound.LC-MS (Method Li): R1 = 1 .95 mm; mlz = 224 (M-H)1H NMR (400 MHz, Chloroform-d, Method M2) 6 7.33 – 7.14 (m, 3H), 5.03 (s, 1H), 4.30 (m, 2H), 1.32 (t, J = 7.1 Hz, 3H).

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; BAYER ANIMAL HEALTH GMBH; KOeHLER, Adeline; WELZ, Claudia; BOeRNGEN, Kirsten; KULKE, Daniel; ILG, Thomas; KOeBBERLING, Johannes; HUeBSCH, Walter; SCHWARZ, Hans-Georg; GOeRGENS, Ulrich; EBBINGHAUS-KINTSCHER, Ulrich; HINK, Maike; NENNSTIEL, Dirk; RAMING, Klaus; ADAMCZEWSKI, Martin; BOeHM, Claudia; (269 pag.)WO2017/178416; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

939-80-0, A common compound: 939-80-0, name is 4-Chloro-3-nitrobenzonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Step 5 4-(Cyclohexylcarbamoylmethylamino)-3-nitrobenzonitrile Cyclohexylcarbamoylmethylcarbamic acid benzyl ester (16.359 g) was hydrogenated using 7.5% palladium carbon (3.24 g) in ethanol (164 ml) solution at atmospheric pressure over 8 hours. After completion of the reaction, the reaction mixture was filtered through celite, and the solvent was evaporated. The obtained residue was dissolved in a mixture of ethanol (50 ml) and isopropanol (50 ml). Thereto were added 4-chloro-3-nitrobenzonitrile (8.23 g) and triethylamine (7.1 ml), and the stirred under reflux for 6 hours. After completion of the reaction, water was added under reflux and the mixture was ice-cooled. The resultant solid was collected by filtration and washed successively with water and diisopropyl ether to give the title compound (10.211 g). 1H-NMR (delta ppm, CDCl3) 1.13 (m, 3H), 1.38 (m, 2H), 1.70 (m, 3H), 1.91 (m, 2H), 3.84 (m, 1H), 4.01 (d, J=5.4 Hz, 2H), 5.76 (brd, 1H), 6.81 (d, J=8.7 Hz, 1H), 7.65 (dd, J=2.1, 8.7 Hz, 1H), 8.54 (d, J=2.1 Hz, 1H), 8.81 (brtr, 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-Chloro-3-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Japan Tobacco Inc.; US6562828; (2003); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

6136-68-1, Adding a certain compound to certain chemical reactions, such as: 6136-68-1, name is 3-Acetylbenzonitrile, 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 6136-68-1.

Step l :OSodium hydride (60% dispersion in oil, 8.27 g, 207 mmol, 3.00 equiv) was added to a solution of 3-acetylbenzonitrile (10.0 g, 68.9 mmol, 1 equiv) in tetrahydrofuran (300 mL). The reaction mixture was stirred at 60 C, and a solution of diethyl carbonate (12.5 mL, 103 mmol, 1.50 equiv) in tetrahydrofuran (60 mL) was added over 45 minutes. The light orange reaction mixture was stirred at 60 C for an additional 2 h, then was cooled to 22 C. Saturated aqueous ammonium chloride solution was added, and the mixture was concentrated to -1/2 volume by rotary evaporation. The resulting residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride solution, and the washed solution was dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated to afford ethyl 3-(3-cyanophenyl)-3-oxopropanoate (15 g, 100%) as a white solid. The crude reaction product was taken into the next step without further purification. Calcd(M+l)+: 218.1, Found: 218.0.

According to the analysis of related databases, 6136-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BROWN, William, Colby; HEIDEBRECHT, Richard, W.; BRUBAKER, Jason; FISCHER, Christian; HENDRIX, John, T.; KELLEY, Elizabeth, H.; MACCOSS, Rachel, N.; METHOT, Joey, L.; MILLER, Thomas; OTTE, Karin, M.; SILIPHAIVANH, Phieng; REGER, Thomas; WILLIAMS, Peter, D.; WISCOUNT, Catherine, M.; WO2011/46774; (2011); 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. 6136-68-1, name is 3-Acetylbenzonitrile, A new synthetic method of this compound is introduced below., 6136-68-1

Example 15; Ar-(4-(3-cyanophenyl)-5-(4-(trifluoromethy])phenoxy)thiazol-2-y])-2-(4- (ethylsulfonyl)phenyI)acetamide; Step 1:; To a solution of 3-acetylbenzonitrile (8 g) in chloroform (50 mL) and ethyl acetate (50 mL) was added copper(II) bromide (25.9 g). The reaction mixture was refluxed overnight. Solid was removed by filtration, and the filtrate was washed with sat. ammonium chloride and brine, dried, and concentrated to give 3-(2-bromoacetyl)benzonitrile (13 g) as a yellow oil. MS(ES?) m/z 225 (MH?).

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; GLAXO GROUP LIMITED; WANG, Yonghui; YANG, Ting; WO2012/100734; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts