Category: nitriles-buliding-blocks

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. 127667-01-0, name is 2-Fluoro-5-methoxybenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 127667-01-0

2-Fluoro-5-methoxy benzonitrile (70 mg, 0.46 mmol, 1.0 equiv.) and hydrazine monohydrate (0.3 ml, 6.0 mmol, 13.0 equiv.) were mixed in n-BuOH (2 ml) and heated the reaction mixture in a microwave oven at 180 0C for 45 mins. After it cooled to room temperature, the product indazole amine was precipitated (purified) by addition of n-hexane or n-heptane solvent. Further the precipitated solid was purified using MeOH: CH2Cl2 (1 :1) solvent. The solid was washed with little water (to remove the excess hydrazine), and was dried for couple of hours to obtain nice crystalline white solid of indazole amine (46 mg) in 60 % yield. HPLC: Shim-pack VP ODS 4.6 x 50 m column, Water: MeOH; 0.1% TFA, RT =1.38; LC-MS; M+H+ = 164.2.

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; LEXICON PHARMACEUTICALS, INC.; WO2008/89307; (2008); A2;,
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Electric Literature of 64248-64-2, The chemical industry reduces the impact on the environment during synthesis 64248-64-2, name is 2,5-Difluorobenzonitrile, I believe this compound will play a more active role in future production and life.

In a 3 L5 4-necked flask that had been evacuated and back-filled with argon, 2,5- difluorobenzonitrile (295.3 ml, 812.0 mmol) and 4-amino-3-methylphenol (100.0 g, 812.0 mmol) were dissolved in dry DMSO (2.75 M) with rapid stirring at room temperature. The solution was evacuated/backfilled with argon (3x). Potassium carbonate (185.2 g, 1340 mmol) (-325 mesh) was added. The reaction mixture was evacuated/backfilled with argon (3x) and warmed to 80 0C (internal probe) for 16 hours. TLC indicated complete conversion. The reaction mixture was cooled to room temperature and poured slowly into 2 L of ice water with rapid stirring. The residue in the round bottom flask was taken up in water repeatedly and poured into the ice water until a total volume of 3 L was achieved and all solids were in the ice water. The suspension was stirred rapidly for 2 hours as it came to room temperature. The brown solids were collected by filtration, washed with water (3 L), air dried, dried with latex dam, and dried under high vacuum at 40 0C for 44 hours to provide 194 g (99 %) of the desired product as a tan solid. MS (APCI +) m/z 243 (M+l) was detected. 1H NMR (400 MHz5 CDCl3) delta 7.38 (m, IH), 7.18 (m5 IH), 6.65-6.85 (m, 5H), 3.60 (br, 2H), 2.17 (s, 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-Difluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; GRONEBERG, Robert; BURGESS, Laurence, E.; HARVEY, Darren; LAIRD, Ellen; MUNSON, Mark; RIZZI, James; RODRIGUEZ, Martha; EARY, Charles, Todd; WATSON, Daniel; WO2007/89646; (2007); A1;,
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Electric Literature of 5414-21-1,Some common heterocyclic compound, 5414-21-1, name is 5-Bromovaleronitrile, molecular formula is C5H8BrN, 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.

Into a four-necked reactor equipped with a thermometer,In a nitrogen stream,5.0 g (30.3 mmol) of 2-hydrazinobenzothiazole was added,Was dissolved in 100 ml of DMF.To this solution were added 20.9 g (152 mmol) of potassium carbonate,5.17 g (30.3 mmol) of 5-bromovaleronitrile was added,And the mixture was stirred at 60 C. for 8 hours.After completion of the reaction,The reaction solution was cooled to 20 C.,The reaction solution was poured into 500 mL of water,And extracted with 500 ml of ethyl acetate.The ethyl acetate layer was dried over anhydrous sodium sulfate.After filtering off sodium sulfate,Ethyl acetate was distilled off under reduced pressure on a rotary evaporator to obtain a yellow solid. This yellow solid was purified by silica gel column chromatography (n-hexane: ethyl acetate = 60: 40) to obtain 3.41 g of Intermediate J (yield: 45.7 mol%) as a white solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromovaleronitrile, its application will become more common.

Reference:
Patent; ZEON CORPORATION; SAKAMOTO, KEI; OKUYAMA, KUMI; KIRIKI, SATOSHI; (84 pag.)JP2017/206504; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, 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 194853-86-6, Quality Control of 4-Fluoro-2-(trifluoromethyl)benzonitrile

4-fluoro-2-trifluorobenzonitrile (55) (994 mg),5,5-dimethylhydantoin (56) (3.37 g),Potassium carbonate (1.11 g) was added to N, N-dimethylformamide (15 mL) and stirred under nitrogen atmosphere at 45 C. for 42 hours.After returning the reaction solution to room temperature, the reaction solution was diluted with ethyl acetate and washed with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel flash column chromatography (developing solvent: chloroform: methanol = 50: 1) to give the title compound (57) (503 mg, yield 32.2%) as a white solid.

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

Reference:
Patent; Kyoto prefectural public university; Suzuki, Takasada; Ito, Yukihiro; Ota, Yosuke; (55 pag.)JP2017/71567; (2017); A;,
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Reference of 17417-09-3, These common heterocyclic compound, 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, 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.

2-Fluoro-5-nitrobenzonitrile (500 mg, 3.01 mmol), 1H-1,2,3-triazole (228.68 mg, 3.31 mmol) and potassium carbonate (832.02 mg, 6.02 mmol) were added to MeCN (10 mL) and stirred at 25 C. for 16 h. The reaction mixture was filtered and the residue was washed with EtOAc (30 mL*2). The combined organic layers were concentrated under reduced pressure to afford a crude yellow solid, which was purified by FCC (petroleum ether/ethyl acetate from 100:0 to 70:30) to afford the title compound (600 mg, 92.6%) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) 6=8.72 (d, J=2.6 Hz, 1H), 8.55 (dd, J=2.4, 9.0 Hz, 1H), 8.42 (d, J=9.3 Hz, 1H), 8.03 (s, 2H).

The synthetic route of 17417-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
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Related Products of 6952-59-6, 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. 6952-59-6 name is 3-Bromobenzonitrile, 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 stirred mixture of aryl or heteroaryl halide(Br, I) (0.5 mmol), potassium mono ethyl malonate (0.75 mmol) in THF (10 mL) taken in a 30 mL microwave vial, was added Pd(OAc)2(5 mol%), Xantphos (5 mol %), MgCl2 (0.75), Et3N ( 0.75mmol), imidazole (1 mmol) followed by Co2(CO)8 (0.15mmol). The vial was sealed immediately and microwave irradiated at 90C for 30min. The reaction mixture was concentrated and diluted with ethyl acetate and water. The ethyl acetate layer was separated, dried over sodium sulphate and concentrated. The crude product obtained was purified by column chromatography to get the pure compound.

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

Reference:
Article; Baburajan, Poongavanam; Elango, Kuppanagounder P.; Tetrahedron Letters; vol. 55; 25; (2014); p. 3525 – 3528;,
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Application of 6330-25-2, These common heterocyclic compound, 6330-25-2, name is 2-Cyano-N-methyl-acetamide, 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.

N -Methyl 2-amino-5-(2-(4-methoxyphenyl)ethyl)thiophene-3-carboxamide (TJ19). To a mixture of 4-(4-methoxyphenyl)butanal 6 (0.5 g, 2.805 mmol), 2-cyano-N- methylacetamide 8 (0.275 g, 2.805 mmol) and sulfur (0.090g, 2.805 mmol) in DMF (10 mL), NEt3(0.851 g, 8.451 mmol, 3 equiv) was added. After stirring the resulting mixture at 60C for 30 hrs, the reaction mixture was added to water (20 mL). Ethyl acetate (20 mL) was added and the organic solution was washed with distilled water (3 chi 20 mL), dried over MgS04, filtered, and then evaporated to dryness to afford the crude product mixture. Purification by column chromatography (silica, eluent CH2CI2- ethyl acetate 90-10) afforded TJ19 (0.27 g, 33%) as an off-white solid. 1H NMR (300 MHz, CDCI3) deltaEta 2.86 (m, 7H); 3.78(s, 3H); 5.57 (s, 2H); 6.64(s, 1 H); 6.81 (d, 2H); 7.06(d, 2H).

Statistics shows that 2-Cyano-N-methyl-acetamide is playing an increasingly important role. we look forward to future research findings about 6330-25-2.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; UNIVERSITA DEGLI STUDI DI FERRARA; BALZARINI, Jan; DEHAEN, Wim; THOMAS, Joice; LIEKENS, Sandra; ROMAGNOLI, Romeo; BARALDI, Pier Giovanni; WO2013/190137; (2013); A2;,
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Electric Literature of 4210-32-6, 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. 4210-32-6, name is 4-(tert-Butyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

BuLi (2.5 M in hexanes, 0.46 mL, 1.14 mmol) wasadded to dry Pri2NH(127.5 mg, 1.3 mmol) in dry THF (2.0 mL) at -78¡ãCand the mixture was stirred at -78¡ãC for 10 min. Compound 41 (200 mg, 1.1 mmol) in dry THF (2.0 mL) was added and the mixturewas stirred for 1 h at -78¡ãC. 4-(1,1-Dimethylethyl)benzonitrile (180 mg, 1.1mmol) in dry THF (2.0 mL) was added and the mixture was stirred for 1 h at-78¡ãC, then at 20¡ãC for 16 h. Water (1.0 mL) was added. The mixturewas diluted with CH2Cl2, washed thrice with brine anddried. Evaporation and washing (EtOH) gave 13c (96.5 mg, 29percent) as a whitesolid: mp 204-206¡ãC; IR nmax3295, 1642 cm-1; 1H NMR ((CD3)2SO)(COSY) d 1.33 (9 H, s, CMe3),2.55 (3 H, s, 5-Me), 6.82 (1 H, s, 4-H), 7.35 (1 H, t, J = 7.6 Hz, 7-H), 7.51 (2 H, d, J= 7.6 Hz, Ph 3,5-H2), 7.54 (1 H, d, J = 7.2 Hz, 6-H), 7.75 (2 H, d, J= 7.6 Hz, Ph 2,6-H2), 8.06 (1 H, d, J = 8.0 Hz, 8-H), 11.48 (1 H, br, NH); 13C NMR((CD3)2SO) (HSQC / HMBC) d 18.75 (Me), 30.97 (CMe3), 34.44 (CMe3),99.60 (4-C), 124.56 (8-C), 124.86 (8a-C), 125.51 (Ph 3,5-C2), 125.72(7-C), 126.56 (Ph 2,6-C2), 131.44 (Ph 1-C), 133.15 (6-C), 133.60(4a-C), 136.69 (5-C), 139.84 (3-C), 151.87 (Ph 4-C), 162.97 (1-C); MS m/z 292.1686 (M + H)+ (C20H22NOrequires 292.1703).

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

Reference:
Article; Paine, Helen A.; Nathubhai, Amit; Woon, Esther C.Y.; Sunderland, Peter T.; Wood, Pauline J.; Mahon, Mary F.; Lloyd, Matthew D.; Thompson, Andrew S.; Haikarainen, Teemu; Narwal, Mohit; Lehtioe, Lari; Threadgill, Michael D.; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5891 – 5908;,
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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. 72054-56-9, name is 4-(2-Bromoethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-(2-Bromoethyl)benzonitrile

Production Example 12 Synthesis of 4-carbamoylphenethyl bromide 4-Cyanophenethyl bromide (0.997 g) was dissolved in sulfuric acid (20 ml) and stirred at room temperature for 15 hr. Then it was poured into ice, diethyl ether was added thereto and the layers were separated. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (0.619 g) as colorless crystals (yield: 62.0%) 1H-NMR (400 MHz, CDCl3): delta(ppm) 3.23(2H, t, J=7.3Hz), 3.59(2H, t, J=7.3Hz), 7.31(2H, d, J=8.4Hz), 7.78(2H, d, J=8.4Hz).

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 72054-56-9.

Reference:
Patent; Eisai Co., Ltd.; US2002/19531; (2002); A1;,
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These common heterocyclic compound, 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, 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. COA of Formula: C8H3ClF3N

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 synthetic route of 2-Chloro-4-(trifluoromethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

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;,
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