Category: nitriles-buliding-blocks

218632-01-0, name is 3-Fluoro-4-nitrobenzonitrile, 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. 218632-01-0

3-Fluoro-4-nitrobenzonitrile (3.50 mmol, 581 mg) in CH2Cl2 (12 mL) was added Et3N (3.85 mmol, 0.54 mL) at -15 C. The reaction solution was stirred at -15 C. for 30 min. To the reaction solution was added 3-methoxypropan-1-amine (3.50 mmole, 0.36 mL) and stirred at -15 C. for 30 min. The cooling bath was removed to let the reaction solution warm to rt and kept stirring at rt for 30 min. The reaction solution containing 3-(3-methoxypropylamino)-4-nitrobenzonitrile (41A) was concentrated in vacuo and carried directly on to the next step without further purification. ESI-MS: m/z 236.3 (M+H)+.

Statistics shows that 218632-01-0 is playing an increasingly important role. we look forward to future research findings about 3-Fluoro-4-nitrobenzonitrile.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US8138168; (2012); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

2973-50-4, 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. 2973-50-4 name is 2-(2-Aminophenyl)acetonitrile, 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.

To a suitable amount of an organic solvent (a mixture of 1-cyanopropyl-3-methylimidazolium tetrafluoroborate and ethylene glycol at a mass ratio of 1: 4)The compound of formula (I) above 100mmo 1 is added,100mmo 1 The compound of formula (II)15 mmo 1 catalyst (3.75 mmol1-diphenylphosphino-1 ‘_ (di-tert-butylphosphino) ferrocene11.25 mmol Tin iodide mixture),150 mmol of base 1,5,7-triazabicyclo [4.4.0] dec-5-ene (TBD) with16 mmol Promoter Cerium triflate (Ce(OTf) 3), then warmed to 80 C, and the reaction was stirred at this temperature for 12 hours;[0036] After completion of the reaction, deionized water was added to the reaction system and thoroughly shaken, washed, and then extracted with chloroform 2-3 times,The combined organic phases were washed again with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was passed over 300-400 meshSilica gel column chromatography eluting with a mixture of acetone and petroleum ether in a volume ratio of 1: 2 to give a compound of the above formula (III)The yield of the compound was 95.7%.

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

Reference:
Patent; Gong Xiaoqian; Bu Gonggaofamingren; (9 pag.)CN105949109; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

623-00-7, Adding a certain compound to certain chemical reactions, such as: 623-00-7, name is 4-Bromobenzonitrile, 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 623-00-7.

General procedure: after standard cycles of evacuation and back-filling with dry and pure nitrogen, an oven-dried Schlenk tube equipped with a magnetic stirring bar was charged with Pd source (see Table 1, Table 2, Table 3 and Table 4), ligand (see Table 1, Table 2, Table 3 and Table 4), N,N-dimethylpyridin-4-amine (DMAP, see Table 1, Table 2, Table 3 and Table 4), and ethyl potassium malonate (see Table 1, Table 2, Table 3 and Table 4). The tube was evacuated and backfilled with argon (this procedure was repeated three times). Under a counter flow of argon, aryl halide (see Table 1, Table 2, Table 3 and Table 4) and solvent (see Table 1, Table 2, Table 3 and Table 4) were added by syringe. The tube was sealed and stirred at room temperature for 10 min. Then the tube was connected to the Schlenk line, which was full of argon, stirred in a preheated oil bath (140-150 C) for the appointed time (20-25 h). Upon completion of the reaction, the mixture was cooled to room temperature and diluted with diethyl ether, and the yields were determined by gas chromatography using 1,3-dimethoxybenzene as the internal standard.

According to the analysis of related databases, 623-00-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Feng, Yi-Si; Wu, Wei; Xu, Zhong-Qiu; Li, Yan; Li, Ming; Xu, Hua-Jian; Tetrahedron; vol. 68; 9; (2012); p. 2113 – 2120;,
Nitrile – Wikipedia,
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170572-49-3, A common compound: 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, 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.

Intermediate 54 2- [4- (5-cyano-2-methylphenoxy)-2-methylphenoxy]-2-methylpropionic acid ethyl ester Step A . 3-fluoro-4-methyl-5-nitrobenzonitrile; Add potassium nitrate (4.51 g, 44.54 mmol) in three or four portions to 3-fluoro-4- methylbenzonitrile (6.02 g, 44.54 mmol) in concentrated H2SO4 (50 ml) at 0C and stir. Stir the deep orange solution for 2 hours at 0C and then for 1 hour at rt. Add the mixture over 800 ml of ice and extract with 150 ml of AcOEt. Allow the mixture to warm at rt and separate the organic layer. Extract again the aqueous layer with 100 ml of AcOEt. Combine the organic extracts and washed with water (50 ml) and brine (50 ml). Dry the organic layer over magnesium sulfate, filter, and concentrate under reduced pressure to give the crude product (7.64 g, 93% yield). Although the product can be used without further purification, flash chromatogapy can be performed in silica using hexane: ethyl acetate (10: 1) as eluent.

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-4-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/54176; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

3218-50-6, Adding a certain compound to certain chemical reactions, such as: 3218-50-6, name is 2,5-Dichlorobenzyl cyanide, 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 3218-50-6.

EXAMPLE 3 Preparation of 2-[1l-[(2,5-dichlorophenyl)acetyl]-4-piperidinyl]-N-methyl-N-[(1R)-1-phenylpropyl]-4-thiazolecarboxamide (Compound 110) Step A: Preparation of 2,5-dichlorobenzeneacetic acid. A mixture of 2,5-dichlorobenzyl bromide (5.4 g, 22.5 mmol) in 16 mL of ethanol and potassium cyanide (1.63 g, 25 mmol) in 4 mL of water was heated at 80 0C overnight, then cooled, and the solids were filtered and washed with ethanol to give 3.5 g of 2,5- dichlorophenylacetonitrile as a white powder melting at 89-91 C. The nitrile was suspended in 20 mL of ethanol, and 20 mL of a 25 % aqueous NaOH solution was added. The mixture was heated in a CEM Explore microwave reactor at 140 0C for 30 minutes, then cooled, poured into ice water and acidified to pH 1 with concentrated HCl to give a precipitate. The precipitate was filtered, washed with water and dried in a vacuum oven at 90 0C for 5 h to give the title compound as a white powder. 1H NMR (CDCl3) delta 3.79 (s, 2H), 7.2-7.4 (m, 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, 2,5-Dichlorobenzyl cyanide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2007/14290; (2007); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

117482-84-5, Adding a certain compound to certain chemical reactions, such as: 117482-84-5, name is 3-Chloro-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 117482-84-5.

EXAMPLE 84B 3-chloro-4-(methylamino)benzonitrile A mixture of 3-chloro-4-fluorobenzonitrile (5.2 g, 33 mmol), THF (55 mL), and 40% methylamine in water (25 mL, 290 mmol) in a sealed tube was heated to 65 C. for 1.5 hours, cooled to room temperature. The organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated. The resulting solid was dried for about 16 hours under high vacuum in the presence of P2O5 to provide 6.3 g (95%) of the desired product. MS (DCI/NH3) m/z 184, 186 (M+H+NH3)+; 1H NMR (DMSO-d6) delta7.72 (d, 1H), 7.55 (dd, 1H), 6.70 (d, 1H), 6.52 (br q, 1H), 2.80 (d, 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, 3-Chloro-4-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Claiborne, Akiyo K.; Gwaltney II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2003/87940; (2003); A1;,
Nitrile – Wikipedia,
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63069-50-1, These common heterocyclic compound, 63069-50-1, name is 4-Amino-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.

A mixture containing 6-bromo-1 -methyl-benzimidazole (2.38 mmol), 4-amino-3-fluoro-benzonitrile (3.57 mmol),XPhos (0.95 mmol), Cs2CO3 (7.14 mmol) and Pd(OAc)2 (0.71 mmol) in dry toluene (8 mE) was stirred at 1100 C. forapproximately 16 h. The mixture was diluted (EtOAc), washed (H20), dried (Na2SO4) and concentrated to yield thedesired product 3-fluoro-4-[(3-methylbenzimidazol-5-yl)amino]benzonitrile.

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 63069-50-1.

Reference:
Patent; GALAPAGOS NV; Menet, Christel Jeanne Marie; Mammoliti, Oscar; Blanc, Javier; Orsulic, Mislav; Roscic, Maja; (81 pag.)US9440929; (2016); B2;,
Nitrile – Wikipedia,
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Some common heterocyclic compound, 2042-37-7, name is 2-Bromobenzonitrile, molecular formula is C7H4BrN, 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. 2042-37-7

EXAMPLE 1 3′-(Imidazo[1,2-alpha]-pyrazin-3-yl)biphenyl-2-carbonitrile A mixture of 2-bromobenzonitrile (9.1 g, 50 mmol), 3-aminobenzeneboronic acid monohydrate (11.6 g, 75 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.73 g, 1.5 mmol) in dimethoxyethane (50 ml) and 2M sodium carbonate solution (25 ml) was heated at 80 C. for 20 h. After cooling to ambient temperature the reaction was partitioned between ethyl acetate (400 ml) and water (400 ml). The organics were washed with brine (400 ml), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel, eluding with isohexane on a gradient of ethyl acetate (0-25%) gave 3′-aminobiphenyl-2-carbonitrile as a colourless oil that solidified on standing to afford a white solid (9.5 g, 98%): deltaH (400 MHz, CDCl3) 3.79 (2H, br), 6.75 (1H, ddd, J 8, 3 and 1), 6.84 (1H, dd, J 3 and 3), 6.92 (1H, dd, J 8 and 3), 7.25 (1H, dd, J 8 and 8), 7.40 (1H, ddd, J 8, 8 and 1), 7.50 (1H, dd, J 8 and 1), 7.62 (1H, ddd, J 8, 8 and 1), 7.73 (1H, dd, J 8 and 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2042-37-7, its application will become more common.

Reference:
Patent; Goodacre, Simon Charles; Hallett, David James; Street, Leslie Joseph; US2004/19057; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 1129-35-7, name is Methyl 4-cyanobenzoate, 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 1129-35-7, 1129-35-7

A mixture of methyl 4- cyanobenzoate (5.0 g, 31.0 mmol) and Omicron,Omicron-diethyl hydrogen dithiophosphate (10.41 g, 62 mmol) in water (100 mL) was stirred at 80 C for 16 h under N2. The mixture was cooled to 20 C and filtered. The precipitate was washed with water (50 mL) and dried under vacuum to give crude methyl 4-(aminocarbothioyl)benzoate (5.93 g, 98%) as a yellow powder: mp (water) 181-184 C; 1H NMR delta 10.04 (br s, 1 H, NH2), 9.65 (br s, 1 H, NH2), 7.83-8.00 (m, 4 H, H-2, H-3, H-5, H-6), 3.88 (s, 3 H, OCH3); MS m/z 196.5 (MH+, 100%).

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, Methyl 4-cyanobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; AUCKLAND UNISERVICES LIMITED; RUGA CORPORATION; GIACCA, Amato; LAI, Edwin; RAZORENOVA, Olga; CHAN, Denise; HAY, Michael, Patrick; BONNET, Muriel; SUN, Connie; TABIBIAZAR, Ray; YUEN, Po-wai; WO2013/155338; (2013); A2;,
Nitrile – Wikipedia,
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26391-06-0, Adding some certain compound to certain chemical reactions, such as: 26391-06-0, name is 2-Cyano-N,N-diethylacetamide, 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 26391-06-0.

Example 1 Crystallographically pure (E)-N,N-Diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide Form C 3,4-Dihydroxy-5-nitrobenzaldehyde (10.0 gm, 54.6 mmol), N,N-diethyl-cyanoacetamide (15.5 gm, 11.06 mmol) and piperidine (15.0 gm, 170.3 mmol) is charged to isopropanol (200 ml). The reaction mixture is heated at reflux for 12 to 15 hours until the starting material is disappeared. After the reaction is complete, the reaction mixture is cooled to room temperature and acetic acid glacial (15 ml) is added. The reaction mixture is concentrated, followed by dilution with ethyl alcohol (50 ml). The mixture is stirred overnight and filtered. The isolated product is dried under vacuum to provide crystallographically pure Form C of crystalline (E)-N, N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide with melting point of 156-160 C. The title product is obtained as a crystalline solid in 75.5% yield. HPLC Purity=99.45% (Z-isomer 0.24%). Mass Spectra=m+1 306.1 (100%).

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 26391-06-0.

Reference:
Patent; Wockhardt Limited; US2008/4343; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts