Month: December 2020

Electric Literature of 214623-57-1,Some common heterocyclic compound, 214623-57-1, name is 5-Amino-2-methoxybenzonitrile, molecular formula is C8H8N2O, 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 2-Methoxyl-5-N-[[4-morpholino]carbonyl]amino benzonitrile To a stirred mixture of 2-methoxyl-5-aminobenzonitrile (2 g, 12.34 mmol), and pyridine (1.28 g, 16.2 mmol) in dried CH2Cl2 (20 mL) was added 4-morpholinecarbonyl chloride (2.42 g, 16.2 mmol). After stirring at RT for 24 h, the mixture was diluted with CH2Cl2 and washed with H2O, brine, dried over MgSO4, concentrated to give an orange solid (3.04 g, 86%) 1H NMR: (400MHz, DMSO-d6): d 3.23 (t, J=4.9 Hz, 4H), 3.47 (t, J=4.9 Hz, 4H), 3.9 (s, 3H), 6.89 (d, J=9 Hz, 1H), 7.3 (d, J=9 Hz, 1H), 8.01 (s, 1H).

The synthetic route of 214623-57-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham Corporation; US6294531; (2001); B1;,
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Related Products of 628-20-6, 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. 628-20-6, name is 4-Chlorobutyronitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under nitrogen protection, 0.5 L of tetrahydrofuran, 103.5 g (1 mol) of 4-chlorobutyronitrile, 2.52 g (0.02 mol) of anhydrous manganese chloride, 387 g (3 mol) of dimethyldichlorosilane,0.31 g of dibromoethane was added to the reactor, stirred and heated to 65 C.0.514g of magnesium turnings were added for the first time. After the reaction was initiated, 25.17g of magnesium turnings were added again for 2 hours. After the reaction was completed, the reaction product was subjected to solid-liquid separation, and the liquid phase was subjected to rectification, and the fraction was collected at a suitable temperature to obtain a cyano group. Organosilicon compound monomer (ie 3-cyanopropyldimethylchlorosilane). The yield of the obtained cyano group-containing organosilicon compound monomer was 96.1%, and the purity was 99.6%.

The synthetic route of 4-Chlorobutyronitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Dongyue Silicone Materials Co., Ltd.; Yi Gang; Hu Qingchao; Wang Chunxiao; Liu Hailong; Guo Jianqiang; Li Yunjie; Sun Jiang; Xiao Yueling; (6 pag.)CN109879902; (2019); A;,
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Application of 1527-89-5, 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. 1527-89-5 name is 3-Methoxybenzonitrile, 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.

General procedure: To an oven-dried 15 mL sealed tube were added 2-aminophenylmethanol 1 (0.425 mmol), benzonitrile 2(0.25 mmol), Ru cat. b (1.94 mg, 1 mol%), and KOtBu (14.02 mg, 0.5equiv) intamyl alcohol (1 mL) under an air atmosphere. The sealedtube was capped and heated at 130C for 2 h. The reaction mixturewas cooled down to room temperature and directly concentratedunder vacuum. The crude mixture was puried by preparative thin-layer-chromatography (petroleum ether/ethyl acetate 20/1) togive the desired product 3 or 4.

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

Reference:
Article; Wan, Xiao-Min; Liu, Zi-Lin; Liu, Wan-Qing; Cao, Xiao-Niu; Zhu, Xinju; Zhao, Xue-Mei; Song, Bing; Hao, Xin-Qi; Liu, Guoji; Tetrahedron; vol. 75; 18; (2019); p. 2697 – 2705;,
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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. 134227-45-5, name is 3,4,5-Trifluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3,4,5-Trifluorobenzonitrile

A solution of l,3-dimethyl-4-(2,4,6-trifluorophenyl)-lH-pyrazol-5-ol (i.e. the product of Step C) (104 mg, 0.43 mmol) in anhydrous N,N-dimethylformamide (2.5 mL) was cooled in an ice-water bath under a nitrogen atmosphere, and sodium hydride (60% suspension in mineral oil, 20 mg, 0.46 mmol) was added in one portion. After 15 minutes, 3,4,5- trifluorobenzonitrile (101 mg, 0.64 mmol) was added in one portion. The reaction mixture was allowed to reach ambient temperature, and then it was heated at 40 C for 2.5 h. Water (~10 mL) was added, and the mixture was extracted with ethyl acetate (2 x ~10 mL). The combined ethyl acetate extracts were sequentially washed with water (3 x 10 mL) and brine, dried (MgS04), and concentrated under reduced pressure. Chromatography on silica gel (5 g), eluting with a 2: 1 mixture of hexanes-ethyl acetate, afforded a product (51 mg) containing the title compound in a 92:8 mixture with its regioisomer..H NMR delta 7.1 (m, 2H), 6.5-6.6 (m, 2H), 3.85 (s, 3H), 2.05 (s, 3H). MS: 380 amu (AP+).

The synthetic route of 134227-45-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; LONG, Jeffrey, Keith; GREGORY, Vann; GUTTERIDGE, Steven; TAGGI, Andrew, Edmund; BEREZNAK, James, Francis; WO2012/31061; (2012); A2;,
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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. 67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., Formula: C8H3F4N

General Procedure A: A solution of an appropriate substituted benzaldehyde (1.65 g, 10.86 mmol) and aryl fluoride (10.26 mmol) in DMF (15 ml_) was treated with K2CO3 (2.83 g, 21.72 mmol), and the mixture was heated in an oil bath at 80 0C for 12 h. The reaction was cooled to RT and partitioned between EtOAc and H2O. The organic phase was washed with water (3x), dried over Na2SO4 and concentrated in vacuo. Silica gel chromtagraphy (EtOAc/hexanes) afforded the pure product.Example 1; 4-r4-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-2-methoxy-phenoxy1-3- trifluoromethvl-benzonitrileA. 4-(4-Formyl-2-methoxy-phenoxy)-3-trifluoromethyl-benzonitrile was prepared from vanillin and 4-fluoro-3-trifluoromethylbenzonitrile following General Procedure A. 1H NMR (400 Hz, CDCI3) ?10.00 (s, 1 H), 8.00 (m, 1 H), 7.68 (dd, 1 H), 7.58-7.53 (m, 2H), 7.29 (d, 1 H), 6.75 (d, 1 H), 3.83 (s, 3H); LC/MS (m/z) [M+1]+ 322.1 (calculated for CI6HH F3NO3, 322.06).

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; JANSSEN PHARMACEUTICA N.V.; WO2008/109727; (2008); A1;,
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Reference of 36282-26-5,Some common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

Sodium hydride (168 mg, 7.02 mmol, 1.0 eq. ) was added to a solution of 6, 6-dimethyl-3-trifluoromethyl-1, 5, 6, 7- tetrahydro-indazol-4-one (1.63 g, 7.02 mmol, 1.0 eq. ) in 35 mL of anhydrous dimethyl sulfoxide. After 15 min 2-bromo-4- fluorobenzonitrile (2.25 g, 11.23 mmol, 1.6 eq. ) was added as a solid. The reaction mixture was heated at 45 0C. After 23 h the reaction mixture was cooled to ambient temperature and quenched with 10 mL of saturated aqueous ammonium chloride. The mixture was diluted with water and extracted with ethyl acetate (4x) . The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified on a Biotage (SiO2, hexanes-ethyl acetate) to afford 2-bromo-4- (6, 6-dimethyl-4- oxo-3-trifluoromethyl-4, 5,6, 7-tetrahydro-indazol-l-yl) – benzonitrile (1.83 g, 63%) as an off-white powder, LC/MS: (M+H) = 412.0.

The synthetic route of 36282-26-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SERENEX, INC.; WO2006/91963; (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. 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 63069-50-1

A mixture of 4-amino-3-fluorobenzonitrile (184 mmol) and NCS (276 mmol) in AcOH (300 mE) was stirred at 70 C. for approximately 16 h. The mixture was concentrated. H20 was added to the residue and the solid product was filtered oil and washed (sat. NaHCO3 and H20). To eliminate H20, THF was added and removed under reduced pressure to yield the desired product.

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;,
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Electric Literature of 328-87-0, A common heterocyclic compound, 328-87-0, name is 2-Chloro-5-trifluoromethylbenzonitrile, molecular formula is C8H3ClF3N, 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.

EXAMPLE I Into 100 ml. of ethanol is added 12.4 g. (0.10 moles) of benzylmercaptan. While nitrogen is bubbled into the solution, 100 ml. of a 1 molar sodium ethoxide in ethanol solution is added. The solvent is evaporated and 100 ml. of anhydrous dimethylformamide is added to the crude solid sodium mercaptide. To the resulting solution is then added 21 g. (0.10 moles) of 4-chloro-3-cyanobenzotrifluoride. The reaction mixture is stirred under nitrogen at room temperature for 1/2 hour and then poured into about 800 ml. of ice-water. After stirring this mixture for 5 minutes, it is extracted with four 200 ml.-portions of ether. The extracts are combined, dried over anhydrous sodium sulfate and evaporated to provide, after drying under high vacuum, a pale yellow oil that crystallizes to a solid upon standing. The yield of crude 2-benzylthio-5-trifluoromethylbenzonitrile is 27.4 g. (94 percent).

The synthetic route of 328-87-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US3954994; (1976); A;,
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Related Products of 7153-22-2, 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. 7153-22-2, name is Ethyl 4-cyanobenzoate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Hydrogenation of 1 mmol of hexyl hexanoate under 20 bar at 100C in toluene, resulted in 99% yield of hexanol (Entry 1). Under the same conditions ethyl butyrate was hydrogenated to give 98% yield of butanol and 91 % yield of ethanol after 50 hours (Entry 2). When the reaction was performed at shorter reaction time (22 hours, Entry 2bis), small amounts of ethyl acetate and butyl butanoate were also formed, attributed to a transesterification reaction with the formed ethanol and butanol. Cyclohexylmethyl acetate gave 99% yield of cyclohexylmethanol and 60% yield of ethanol (Entry 3), and no transesterification products were observed. Hydrogenation of the secondary aliphatic ester heptan-2-yl acetate resulted in 98% yield of heptane-2-ol and 57% yield of ethanol (Entry 4). Ethyl 3-phenylpropanoate was smoothly hydrogenated, rendering 99% yield of 3-phenylpropan-l-ol and 70% yield of ethanol after 21 hours (Entry 5). Similarly, ethyl 3- phenylpropanoate gave 99% yield of phenyknethanol and 74% yield of butanol after 22 hours (Entry 6). In order to get full hydrogenation of benzyl benzoate longer reaction time was needed (43 hours, 99% yield benzyl alcohol, Entry 7). Similarly, methyl benzoate gave 96% yield of benzyl alcohol and 63 % of methanol after 50 hours (Entry 8). epsilon-Caprolactone was smoothly and quantitatively hydrogenated to 1 ,6-hexanediol (99% yield, Entry 9). The activated benzyl trifluoroacetate gave 99% yield of benzyl alcohol and 78% of 2,2,2- trifluoroethanol (Entry 10), and no secondary products where observed. Gratifyingly, allyl trifluoroacetate gave 97% yield of 2,2,2-trifluoroethanol and 96% of allyl alcohol (Entry 1 1), showing high chemoselectivity to ester hydrogenation over C=C hydrogenation. Hydrogenation of ethyl 4-isocyano-benzoate required an increase of precatalyst loading to 3%, probably due to competing nitrile coordination, and resulted in 61 % yield of (4-isocyanophenyl)methanol and 66% yield of ethanol, with no hydrogenation of the nitrile group detected (Entry 12).

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

Reference:
Patent; YEDA RESEARCH AND DEVELOPMENT CO. LTD.; NERUSH, Arkadi; MILSTEIN, David; VOGT, Matthias; MUKHERJEE, Arup; ESPINOSA-JALAPA, Noel Angel; CHAKRABORTY, Subrata; (194 pag.)WO2017/137984; (2017); A1;,
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Synthetic Route of 90110-98-8, 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. 90110-98-8, name is 3-Bromo-4-(hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

At 0-10C, anhydrous ethanol (27 mL) was slowly added dropwise into a mixture of selenium powder (2.7 g, 34.2 mmol) and sodium borohydride (1.57 g, 41.5 mmol), then heated to room temperature and stirred for 30 min, and then added with pyridine solution (7.2 mL) containing 3-bromo-4-isopropylthiomethyl benzonitrile (63) (1.8 g, 8.49 mmol). The reaction solution was heated until reflux occurred, slowly added dropwise with 2M hydrochloric acid solution (18 mL) and then stirred under reflux for 1 h. A TLC analysis indicated that the reaction was completed. The solution was cooled to room temperature, added with a proper amount of water and then extracted with ethyl acetate (30 mL¡Á3). The organic phase was respectively washed with 2M hydrochloric acid (20 mL) and saturated saline solution (20 mL), and dried with anhydrous sodium sulfate. The solvent was removed by means of reduced pressure distillation, so as to obtain pink 3-bromo-4-hydroxymethyl selenobenzamide (64) (1.98 g), with a yield of 79.6%.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-4-(hydroxymethyl)benzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Atom Bioscience and Pharmaceutical Co. Ltd.; SHI, Dongfang; FU, Changjin; WU, Jie; LIU, Jun; EP2927219; (2015); A1;,
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