Category: nitriles-buliding-blocks

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 960370-97-2 as follows. name: 1-Cyclopropyl-4-oxocyclohexanecarbonitrile

e). To the ketone prepared in step d (6.0 g, 37 mmol) in dichloroethane (110 mL) was added cyclopropylamine (3.1 mL, 44 mmol). The solution was cooled to 0 C. (ice bath), and NaBH(OAc)3 (12 g, 55 mmol) and AcOH (2.8 mL, 48 mmol) were added. After 5 minutes the ice bath was removed. The reaction was stirred at room temperature for 4 h. The contents were diluted with CH2Cl2 (100 mL) poured in water (100 mL). The aqueous layer was brought to pH 2 with 5 N HCl. Following removal of the organic layer, the aqueous layer was brought to pH 12 with 5 N NaOH and extracted with 10% MeOH in CH2Cl2 (3¡Á35 mL). The combined organics were dried with Na2SO4 and concentrated in vacuo. Silica gel chromatography (gradient of 5 to 10% ethyl acetate in hexanes with 2.5% triethylamine additive) gave the cis amine followed by the trans amine. 1H NMR (500 Hz, CDCl3, trans isomer): delta 0.15-0.17 (m, 2H), 0.25-0.29 (m, 2H), 0.34-0.37 (m, 4H), 0.58-0.63 (m, 1H), 1.22-1.31 (m, 4H), 1.84-1.90 (m, 4H), 1.96-2.00 (m, 1H), 2.38-2.40 (m, 1H).

According to the analysis of related databases, 960370-97-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Amgen Inc.; US2007/299080; (2007); A1;,
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Application of 30041-95-3, These common heterocyclic compound, 30041-95-3, name is Ethyl 2-(4-cyanophenoxy)acetate, 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.

General procedure: B(C6F5)3 (67.3 mg, 0.13 mmol, 5 mol %) was added to a stirred solution of 3,4-dichlorobenzaldehyde (172 mg, 1 mmol) and NaN3 (97.5 mg, 1.5 mmol) in DMF (5 mL) and was heated at 120 C. After completion of reaction (as monitored by TLC), the reaction mixture was cooled to room temperature and was added 5 mL of cold water followed by 10 mL of 2 N HCl and 10 mL of ethyl acetate. The resulting mixture was stirred vigorously for 15 min. The organic layer was separated and aqueous layer was again extracted with ethyl acetate (3 ¡Á 15 mL). The combined organic layer was washed with water and dried over anhydrous sodium sulfate and was evaporated under reduced pressure. The crude product was purified by column chromatography (silica gel, EtOAc/hexane 9:1) to obtain pure 5-(3,4-dichlorophenyl)-1H-tetrazole. The known compounds were characterized and confirmed by comparison of their spectral data and physical properties with reported literature.

Statistics shows that Ethyl 2-(4-cyanophenoxy)acetate is playing an increasingly important role. we look forward to future research findings about 30041-95-3.

Reference:
Article; Prajapti, Santosh Kumar; Nagarsenkar, Atulya; Babu, Bathini Nagendra; Tetrahedron Letters; vol. 55; 24; (2014); p. 3507 – 3510;,
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Synthetic Route of 72291-30-6, 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. 72291-30-6, name is Methyl 2-cyano-2-methylpropanoate, This compound has unique chemical properties. The synthetic route is as follows.

The reactant and the catalyst are initially charged in the autoclave and the contents are inertized by purging with nitrogen. Subsequently, 5 bar of hydrogen are injected. The desired amount of ammonia is metered in and then the autoclave is heated slowly with stirring to the reaction temperature (80 C.). This step takes an average of 90 min, i.e. the delay time of the reactant solution in contact with ammonia is approx. 90 min. On attainment of the reaction temperature, hydrogen is injected rapidly to the pressure specified in Table 1 below and consumed hydrogen is replaced by metering under pressure control over the experiment time until no further hydrogen absorption is recorded.The autoclave experiments are carried out in a 2.5 l autoclave with hollow-shaft disk stirrer (stirrer speed approx. 600 rpm), electrical heating and jacket air cooling, 2 baffles, sparging through the autoclave lid and introduction of the hydrogen via the hollow-shaft stirrer. The weights for Raney catalysts are corrected for 10% water moisture, i.e., in real terms, 10% more water-moist catalyst is weighed out than specified. Reaction effluents are analyzed via gas chromatography (GC) (conditions: 60 m DB1701; internal diameter 0.32 mm; film thickness 0.25 mum; detector: FID; temperature program: 80 C.?10 K/min?280 C., 40 min, split ratio 100:1, carrier gas helium) and the compositions are reported in % by weight.The reactor yield is determined by means of gas chromatography with internal standard (I.S.) (I.S. piperidine; the concentration thus obtained in the crude effluent is multiplied by the total mass of the crude effluent and the yield thus calculated is compared to the theoretical yield). The reactions are all carried out with methyl 2-cyano-2,2-dimethylacetate with a purity of >99.8%. The main product obtained is aminopivalinamide (3-amino-2,2-dimethylpropionamide). TABLE 1 Pressure/ % by weight ConcentrationNH3/ Purity Conversion Reactor Example bar Catalyst of catalyst Solvent % nitrile (crude, GC) % % yield % 1 200 Ra-Ni 10 NMP 30 20:1 98.7 100 not determined 2 65 Ra-Co 10 BuOH 40 7.7:1 98.8 100 94.0% 3 65 Ra-Ni 10 BuOH 40 7.7:1 98.2 99.7 90.6% 4 65 Ra-Ni 2.5 BuOH 40 3:1 93.7 99.7 84.9% 5 65 Ra0Co 2.5 BuOH 40 3:1 94.9 99.9 86.7 6 65 Ra-Co 5 MeOH 40 3:1 96.5 99.1 90.4 7 65 Ra-Co 5 MeOH 40 3:1 96.6 99.1 91.1 8 65 Ra-Co 5 BuOH 40 3:1 90.0 99.4 88.2 The examples show that very good selectivities of at least 90% are achievable with Raney nickel and Raney cobalt. The higher the amount of ammonia, the higher the catalyst concentration and the higher the hydrogen pressure, the better is the selectivity. In example 8, a metal determination is carried out, 430 ppm of Co are found in the reaction effluent.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-cyano-2-methylpropanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BASF SE; US2008/306299; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 5332-06-9, name is 4-Bromobutanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 5332-06-9

To a stirred solution of 100 mg (0.26 mmol) of 1′-[(6-chloro-1H-indol-3-yl)carbonyl]-3H-spiro[2-benzofuran-1,4′-piperidine] (the preparation of which has been described in example 69) in 5 ml DMF was added 11.5 mg (0.28 mmol) NaH (60% in oil). The mixture was stirred at RT for 30 min. and then 35 mg (0.26 mmol) of 4-bromo-butyronitrile was added. The mixture was stirred for two days at RT and then poured onto water and extracted with ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Flash chromatography (EtOAc/Hx, 2:1; SiO2) afforded 99 mg (88%) of 4-[6-chloro-3-(1’H,3H-spiro[2-benzofuran-1,4′-piperidin]-1′-ylcarbonyl)-1H-indol-1-yl]butanenitrile as a white solid. ES-MS m/e (%): 434(M+H+).

According to the analysis of related databases, 5332-06-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bissantz, Caterina; Grundschober, Christophe; Ratni, Hasane; Rogers-Evans, Mark; Schnider, Patrick; US2007/27173; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 591769-05-0, name is 3-Cyclopentylacrylonitrile, 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 591769-05-0, SDS of cas: 591769-05-0

To a solution of 4-[3-(difluoromethyl)-1H-pyrazol-4-yl)-7-{[2-(trimethylsilyl)ethoxy] methyl}-7H-pyrrolo[2,3-d]pyrimidine (1.0 eq.) and 3-cyclopentylacrylonitrile (2.5 eq., prepared from the step A of Example 1) in acetonitrile was added 1,8-diazabicyclo[5.4.0]undec-7-ene (2.0 eq.) at room temperature. The reaction liquid was stirred for 5 hrs at room temperature, then warmed to 60¡ãC and stirred overnight. After the reaction liquid was cooled to room temperature, the reaction liquid was diluted with brine and ethyl acetate, and extracted with ethyl acetate. The combined organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The resulting residue was separated by column chromatography on silica gel column to give the titled compound. m/z=487[M+1]+.

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

Reference:
Patent; Centaurus BioPharma Co., Ltd.; Chia Tai Tianqing Pharmaceutical Group Co.,Ltd; Lianyungang Runzhong Pharmaceutical Co., Ltd.; ZHU, Li; XIAO, Dengming; HU, Yuandong; DAI, Liguang; DUAN, Xiaowei; SUN, Yinghui; PENG, Yong; KONG, Fansheng; LUO, Hong; HAN, Yongxin; YANG, Ling; WANG, Shanchun; (94 pag.)EP3235819; (2017); A1;,
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Related Products of 2941-29-9, 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. 2941-29-9, name is Cyclopentanone-2-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Example 91 2-Ethyl-2,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-amine (CF91) 2-Oxocyclopentanecarbonitrile (1.5 g, 14 mmol), sodium acetate (3.4 g, 42 mmol), and ethyl hydrazine-oxalate (4.2 g, 28 mmol) were mixed in ethanol, and the mixture was heated at reflux for overnight. The reaction mixture was cooled to room temperature and ethanol was removed on a rotary evaporator. Water was added and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated on a rotary evaporator. The remaining residue was purified by flash column chromatography to yield CF91 in 1.03 g. 1H NMR (300 MHz, CDCl3): 3.92 (q, J=7.23 Hz, 2H), 3.40-3.20 (m, 2H, NH), 2.62 (t, J=7.19 Hz, 2H), 2.54-2.44 (m, 2H), 2.40-2.28 (m, 2H), 1.38 (t, J=7.24 Hz, 3H). ESI-MS calculated for C8H14N3 [M+H]+=152.12; Observed: 152.33

The chemical industry reduces the impact on the environment during synthesis Cyclopentanone-2-carbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; Wang, Shaomeng; Zhao, Yujun; Zhou, Bing; Aguilar, Angelo; Liu, Liu; Bai, Longchuan; McEachern, Donna; Sun, Duxin; Wen, Bo; Luo, Ruijuan; Zhao, Ting; Chinnaiyan, Arul; Asangani, Irfan A.; Stuckey, Jeanne; Meagher, Jennifer Lynn; Ran, Xu; US2015/246923; (2015); A1;,
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Synthetic Route of 59997-51-2, These common heterocyclic compound, 59997-51-2, name is 4,4-Dimethyl-3-oxopentanenitrile, 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.

Step C: 5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-ylamine A solution of p-tolyl-hydrazine hydrochloride (15.86 g, 100 mmol) and pivaloylacetonitrile (17.9 g, 143 mmol) dissolved in MeOH (65 mL) was heated to reflux for 18 hours under N2 atmosphere. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was triturated with ether and collected by filtration. The solid was dried under high vacuum to provide 26.6 g of white solid (99% yield).

The synthetic route of 59997-51-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Munson, Mark; Mareska, David A.; Kim, Youngboo; Groneberg, Robert D.; Rizzi, James; Rodriguez, Martha; Kim, Ganghyeok; Vigers, Guy; Rao, Chang; Balachari, Devan; Harvey, Darren; US2004/192653; (2004); A1;,
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Related Products of 120315-65-3, 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. 120315-65-3, name is 4-Bromo-3-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 4-bromo-3-methoxybenzonitrile (1.4 g, 6.7 mmol), allyl-tributyl-stannane (2.7 g, 8.1 mmol), LiCl (0.86 mg, 20 mmol) and Pd(PPh)4 (0.2 g) in 25 mL of anhydrous toluene was refluxed under N2 overnight. Checked the reaction with TLC and concentrated under reduced pressure. The residue was purified by silica gel cloumn chromatography to give the product 4-allyl-3-methoxybenzonitrile. MS m/z: 174 (M+1)+.

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-Bromo-3-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Sharp & Dohme Corp.; TANG, Haifeng; PASTERNAK, Alexander; YANG, Lihu; WALSH, Shawn, P.; PIO, Barbara; SHAHRIPOUR, Aurash; TEUMELSAN, Nardos; (111 pag.)EP2632465; (2015); B1;,
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Reference of 57381-49-4, A common heterocyclic compound, 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, molecular formula is C7H3BrClN, 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.

[1,1′-bis(diphenylphosphino)dicene. Iron] Palladium dichloride (192.8 mg, 0.26 mmol) and potassium carbonate (1.09 g,7.91mmol) wereadded. The reaction mixture was heated to 110C and the reaction was stirred for 16 hours.The reaction solution was allowed to cool to room temperature and20 mL of water was addedto the reaction mixture. The mixture was extracted with ethyl acetate (20 mL ¡Á 3). The organic phases were combined and the organic phase was washed with saturated sodium chloride solution (20 mL ¡Á2) and dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure.The resulting residue was purifiedby silica gel column chromatography using an eluent system C togive the crude title product 4d (450 mg, yellow viscous product), which was directly introduced into the next reaction.

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; Jiangsu Hengrui Pharmaceutical Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; Yang Fanglong; Chi Jiangtao; He Feng; Tao Weikang; (33 pag.)CN107793396; (2018); A;,
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Synthetic Route of 6574-97-6, These common heterocyclic compound, 6574-97-6, name is 2,3-Dichlorobenzonitrile, 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.

Take dried 2L flask was refluxed for four devices, under nitrogen, into sulfolane 1200g, 280g of potassium fluoride, tetramethylammonium chloride 50g, 2,3- dichlorobenzonitrile 688g, open stirring slowly raised to 210 reaction was incubated 8h, the control sample, the end of the reaction raw material ?1percent.The reaction solution was added to a short column distillation, to give 2-fluoro-3-chlorobenzonitrile 560g, content ?99percent, yield 90percent.

The synthetic route of 6574-97-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Yongtai Technology Co ., Ltd; Zhang, xing; Shu, zhujin; (10 pag.)CN104529729; (2016); B;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts