Month: July 2021

Some common heterocyclic compound, 21524-39-0, name is 2,3-Difluorobenzonitrile, molecular formula is C7H3F2N, 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. Computed Properties of C7H3F2N

2,3-difluoro-5-nitrobenzonitrile (0272) At 0 C., to a solution of 2,3-difluorobenzonitrile (20.8 g, 149.82 mmol) in sulfuric acid (100 mL) was added potassium nitrate (30.3 g, 299.59 mmol) in portions over 1 h period. The resulting solution was kept stirring for 2 h at 0 C. and then ice water (500 mL) was added. The resulting mixture was extracted with ethyl acetate (300 mL×3). The organic phases were combined, washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with ethyl acetate in hexane (0% to 10% gradient) to yield 2,3-difluoro-5-nitrobenzonitrile as brown solid (3.6 g, 13%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 21524-39-0, its application will become more common.

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; KARRA, Srinivasa; XIAO, Yufang; (407 pag.)US2016/376283; (2016); A1;,
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Synthetic Route of 654-70-6, These common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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.

At 0C,Compound 16a (25.00 g, 134.31 mmol)Liquid bromine (21.68 g, 135.66 mmol) was slowly added dropwise to a solution of methanol (200 mL).The resulting reaction solution was continuously stirred for 0.5 hours.At 0C,Saturated sodium thiosulfate solution (200 mL) was added to the reaction system to quench the reaction, then diluted with water (1000 mL), filtered, and the solid was washed with water (200 mL×3).After drying under reduced pressure, compound 16b (34.30 g) was obtained.

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

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Nanjing Mingde Drug Discovery Co., Ltd.; Yao Yuanshan; Chen Bin; Chen Yuan; Li Ao; Xu Ran; Huang Zhensheng; Tian Dongdong; Li Hongwei; Yang Chengshuai; Li Jian; Chen Shuhui; (30 pag.)CN107954995; (2018); A;,
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Related Products of 7357-70-2, 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 7357-70-2 as follows.

ferf-butyl 4-(4-(3-amino-2-cyano-3-thioxoprop-1 -enyl)-3- nitrophenyl)piperazine-1 -carboxylate1.5 g (15 mmol) of 2-cyanoethanethioamide, 60 ml of ethanol and one drop of piperidine are added respectively to 5 g (15 mmol) of tert-butyl 4-(4-formyl-3- nitrophenyl)piperazine-l -carboxylate. The reaction mixture i s sti rred at room temperature for 12 hours. The precipitate obtained is filtered to yield 5.2 g (83%) of tert-b u t y 1 4-(4-(3-amino-2-cyano-3-thioxoprop-l-enyl)-3-nitrophenyl)piperazine-l- carboxylate in the form of a yellow solid.LCMS (ESI, m/z): (M+l) 418.481H MR: 6H pm 400 MHz, DMSO: 10.10 (IH, bs, NH), 9.45 (IH, bs, NH), 8.25 (IH, CHarom), 7.95 (IH, d, CHarom), 7.60 (IH, d, CHarom), 6.35 (IH, dd, CHarom), 3.50 (8H, i 4CH2), 1.42 (9H, s, 3CH3).

According to the analysis of related databases, 7357-70-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PIERRE FABRE MEDICAMENT; RABOT, Remi; BEDJEGUELAL, Karim; KALOUN, El Bachir; SCHMITT, Philippe; RAHIER, Nicolas; MAYER, Patrice; FOURNIER, Emmanuel; WO2012/140114; (2012); A1;,
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Electric Literature of 77668-42-9, A common heterocyclic compound, 77668-42-9, name is 2,3-Dichlorobenzoyl cyanide, molecular formula is C8H3Cl2NO, 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.

In the reactor was added 40g aminoguanidine carbonate and 200ml of methanol (entrainer)30g concentrated sulfuric acid was added dropwise with stirring, the addition was completed dropwise distillation entrainer,And bring out the water, suction filtration,Solid into the reaction flask, at 80 C under reduced pressure and drained.Adding 2,3-dichlorobenzoyl cyanide solution obtained in step (1), heating to 80 C., reacting for 3 h to the end of the reaction, lowering to room temperature, and filtering by suction to obtain white sand particles;

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; Zhejiang Qicai Environment Technology Co., Ltd.; Jin Cheng; Chen Lina; Liang Wei; Zhang Tong; Chen Lei; (6 pag.)CN106083753; (2016); A;,
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Related Products of 16588-02-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To solution of 1.97 mmol (1.2 eq.) of phenol 2-8, 12-13 in 3 ml dry DMSO was added 79 mg(1.2 eq.) powdered NaOH. The mixture was heated at 50C for 20 min and to the formed clearsolution 0.300 g (1.64 mmol, 1.0 eq.) of 1 was added. The reaction mixture was heated at 80C for 8h. After cooling 40 ml water was added and extracted with DCM. The organic phase was washedwith aq. NaHCO3 and water, dried over Na2SO4, filtered and evaporated in vacuo. The crudeproducts 14-20, 24-25 were purified by column chromatography (50 g silica-gel). After column theformed solid products were powdered, washed with 3 ml hot hexane and dried in vacuo.

The synthetic route of 2-Chloro-5-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dobrikov, Georgi M.; Slavchev, Ivaylo; Nikolova, Ivanka; Stoyanova, Adelina; Nikolova, Nadya; Mukova, Lucia; Nikolova, Rosica; Shivachev, Boris; Galabov, Angel S.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 19; (2017); p. 4540 – 4543;,
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Reference of 63069-50-1, 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 63069-50-1 as follows.

Specifically, oxalyl chloride (0.72 mL, 8.36 mmol) was added over 10 min to a solution of linoleic acid (2 mL, 6.43 mmol) and DMF (3 drops) in DCM (10 mL) at 0 C, and the solution stirred at room temperature overnight. The solvent and excess oxalyl chloride was removed in vacuo and the residue redissolved in DCM (10 mL). This solution was added dropwise to a solution of 3-fluoro-4-aminobenzonitrile (0.79 g, 5.79 mmol) in DCM (10 mL) and Et3N (1 mL) that had been cooled in an ice bath. Upon complete addition, the solution was stirred at room temperature overnight. The solution was washed with saturated Na2C03 solution (3 chi 20 mL), H20 (20 mL), and brine (20 mL), and dried over MgS04. The resulting residue was subjected to column chromatography, using a gradient elution of EtOAc/petroleum spirits to afford the product as a pale yellow oil that solidified upon cooling. (0597) [00453] Yield: 0.98 g (39%). (0598) [00454] FT- 1 (ATR) Vmait crrr1 : 3328 br w, 2925 m, 2855 m, 2232 w, 1709 m, 1616 m, 1594 m, 1517 s. 1 H-NMR delta/ppm (d6-DMSO): 10.07 (1 H, s, NH) , 8.32 (1 H, m, Ar CH), 7.91 (1 H, dd, 3JH,F = 1 1 .1 Hz, 4JH,H = 1 .9 Hz, Ar CH), 7.68 (1 H, ddd, 3JH,H = 8.6 Hz, 4JH,H = 1 .9 Hz, 5JH,F = 0.9 Hz Ar CH), 5.28 – 5.43 (4 chi 1 H, 4 chi m, 4 chi olefinic CH), 2.77 (2H, m, CH2), 2.48 (2H, m, NHCOCH2), 2.00 – 2.10 (2 x 2H, 2 x m, 2 x CH2), 1 .61 (2H, m, CH2), 1 .24 – 1 .40 (7 chi 2H, 7 chi m, 7 chi CH2), 0.88 (3H, m, CH3). 13C-NMR delta/ppm (d6-DMSO): 172.4 (CONH), 151 .7 (d, 1 JC,F = 247 Hz, Ar CF), 131 .6 (d, 2JC,F = 1 1 .2 Hz, Ar C), 129.70 (olefinic CH), 129.68 (olefinic CH), 129.3 (d, 3JC,F = 3.5 Hz, Ar CH), 127.74 (olefinic CH), 127.71 (olefinic CH), 122.9 (d, 4JC,F = 2.9 Hz, Ar CH), 1 19.3 (d, 2JC,F = 23.4 Hz, Ar CH), 105.7 (d, 3JC,F = 9.3 Hz, Ar C), 1 17.9 (d, 3JC,F = 2.7 Hz, CN), 35.9 (NHCOCHs), 30.9 (CH2), 29.0 (CH2), 28.7 (CH2), 28.6 (CH2), 28.52 (CH2), 28.5 (CH2), 26.6 (CH2), (0599) 25.2 (CH2), 24.9 (CH2), 21 .9 (CH2), 13.9 (CH3).

According to the analysis of related databases, 63069-50-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CURTIN UNIVERSITY; FALASCA, Marco; MASSI, Massimiliano; SIMPSON, Peter, Vernon; (181 pag.)WO2019/40992; (2019); A1;,
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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. 3288-99-1, name is 2-(4-(tert-Butyl)phenyl)acetonitrile, A new synthetic method of this compound is introduced below., Product Details of 3288-99-1

In a 300 mL-reaction flask equipped with a rectification column and a separating tank, 11.3 g (65.2 mmol) of 4-tert-butylphenylacetonitrile, 10.8 g (59.5 mmol) of 1,3,4-trimethylpyrazol-5-carboxylic acid ethyl ester, 100 g of heptane, 10.0 g of 5-ethyl-2-picoline were added, the atmosphere was substituted with nitrogen, then azeotropic dehydration was carried out by heating at 90 to 95 C. for 1 hour. The temperature was maintained, 13.8 g (71.5 mmol) of 28% sodium methoxide methanol solution was added dropwise over 3 hours, and the resulting mixture was further reacted for 11 hours. After cooling to 30 C. or less, 108 g of water was added to separate out heptane phase and obtain an aqueous phase. A quantitative analysis of the obtained aqueous phase with liquid chromatography showed that the aqueous phase contained 15.5 g (yield 84.5%) of 3-oxo-2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl)propionitrile.

The synthetic route of 3288-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fukuda, Kenzo; Kondo, Yasuo; Tanaka, Norio; Suzuki, Hideaki; Ohnari, Masatoshi; Nishio, Koichi; US2006/178523; (2006); A1;,
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Electric Literature of 13531-48-1,Some common heterocyclic compound, 13531-48-1, name is Methyl 3-cyanobenzoate, molecular formula is C9H7NO2, 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 3-Cyanobenzoic acid methyl ester (50g, 310 mmol) in ethanol(500 mL) was added 50% aqueous hydroxylamine (41 mL, 620 mmol) at room temperature. The reaction mixture was stirred for 1 h at 100 0C and the solvents were removed under reduced pressure. The oily residue was dissolved in 20/80 ethanol/toluene (50 mL x 2) and then concentrated again. The desired ester (6 Ig, quan. yield) was obtained as a white powder with 98% purity (LC/UV). 1H-NMR (CDCl3) delta 9.76 (IH), 8.24 (IH), 7.82 (2H), 7.51 (IH), 5.92 (2H), 3.82 (3H).

The synthetic route of 13531-48-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; WO2006/110483; (2006); A1;,
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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. 6629-04-5, name is N-Cyanoacetylurethane, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

General procedure: To the mixture of substituted anilines (0.08mol), concentrated hydrochloric acid (45.0mL) and water (120.0mL), aqueous solution of NaNO2 (60.0mL, 0.11mol) was added drop-wise under stir at a rate that the temperature below 0C, and the reaction mixture was stirred for 0.5h. A mixture of ethyl (2-cyanoacetyl)carbamate (13.7g, 0.09mol) and sodium acetate (24.0g, 0.27mol) in ethanol (400.0mL) was added drop-wise to the resulting diazonium salt solution below 0C and stirred for a further 2h. The precipitate was collected by filtration and washed with water (40.0 mL×2), dried to give compounds 7a-f.

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 6629-04-5.

Reference:
Article; Zhao, Sijia; Zhang, Yu; Zhou, Hongyang; Xi, Shuancheng; Zou, Bin; Bao, Guanglong; Wang, Limei; Wang, Jiao; Zeng, Tianfang; Gong, Ping; Zhai, Xin; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 37 – 50;,
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149793-69-1, name is 3-Fluoro-5-(trifluoromethyl)benzonitrile, 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. Safety of 3-Fluoro-5-(trifluoromethyl)benzonitrile

Reference Compound 1C and ID sodium 3-(4-(pyrrolidin-l-yl)piperidin-l-yl)-5-(trifluoromethyl)benzoate and 3-(4- (pyrrolidin-l-yl)piperidin-l-yl)-5-(trifluoromethyl)anilineScheme 1: Synthesis of Reference Compound 1 (compounds 1-C and 1-D) 1-A 1-B 1 -C [0079] Reagents and conditions: (a) 4-(pyrrolidine-l-yl) piperidine, K2CO3, DMSO,800C; (b) i. 50% H2SO4, reflux; ii. NaOH, 2 steps; (c) DPPA, Et3N, DCM, rt; (d). TFA,DCM, rt.[0080] 1-B: To a stirred solution of 1-A (6.49 g, 34.2 mmol) in 50 mL of DMSO is added 4-(pyrrolidine-l-yl) piperidine (5.80 g, 37.6 mmol) and K2CO3 (5.20 g, 37.6 mmol) at room temperature. The reaction mixture is stirred at 80 0C for 1 hour. HPLC/MS test indicates the complete consumption of I- A) and a single new peak with the right mass for 1-B ([M+l] = 324).[0081] The reaction mixture is diluted with ethyl acetate and washed with water and brine. The organic solution is dried over Na2SO4 and concentrated. The crude product is used directly in the next step without further purification.

The synthetic route of 149793-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; DANA FARBER CANCER INSTITUTE; WO2009/152356; (2009); A2;,
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