Month: August 2021

Synthetic Route of 658-99-1,Some common heterocyclic compound, 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile, molecular formula is C8H5F2N, 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: To a stirring solution of substituted benzonitrile/phenylacetonitrile (1mmol) in anhydrous methanol (20mL) under N2 atmosphere was added hydroxylamine hydrochloride (1.2mmol). Triethylamine (2.5mmol) was added under continuous stirring condition and the mixture was then heated under reflux condition for overnight at 60C and continued until complete consumption of the starting material (monitored by TLC) [22,23]. The excess solvent was then removed under reduced pressure and the obtained residue was washed successively with water and brine, and extracted with ethylacetate (3×10mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. This reaction mixture was purified using silica gel column chromatography with a gradient solvent system of 10-20% ethylacetate to hexane to obtain the desired product with an average yield of 70-80%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3,4-Difluorophenyl)acetonitrile, its application will become more common.

Reference:
Article; Paul, Saurav; Roy, Ashalata; Deka, Suman Jyoti; Panda, Subhankar; Trivedi, Vishal; Manna, Debasis; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 364 – 375;,
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Related Products of 179898-34-1, 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. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

5′-(3-Cyano-5-fluorophenyl)-spiro[cyclopentane-1,3′-[3H]indol]-2′(1’H)-one: A solution of 3-cyano-5-fluoro-bromobenzene (0.5 g, 2.6 mmol), and tetrakis (triphenylphosphine)palladium(0) (0.2 g) in ethylene glycol dimethyl ether (20 cm3) was stirred under N2 for 20 minutes. To this mixture was then (spiro[cyclopentane-1,3′-[3H]indol]-2′(1’H)-one-5-yl) boronic acid (0.9 g, 3.9 mmol) and sodium carbonate (0.8 g, 7.8 mmol) in water (5 cm3). The solution was brought to reflux for 18 hours and then cooled to room temperature, poured into 2N NaOH and extracted with EtOAc (×3). The combined extracts were washed with water, brine, dried (MgSO4), and evaporated. The residue was purified by column chromatography (SiO2, EtOAc, hexane) to afford the subtitled compound (0.35 g, 44%) as white needles. mp: 235-237 C.; 1H NMR (DMSO-d6) delta 10.5 (s, 1H), 8.1 (s, 1H), 8.0 (dt, 1H, J=1.7, 2.0, 7.0 Hz), 7.8-7.7 (m, 2H), 7.6 (dd, 1H, J=1.8, 6.4 Hz), 6.9 (d, 1H, J=8.1 Hz), 2.0-1.9 (m, 8H); MS (EI) M+ m/z 306.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-5-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceuticals, Inc.; US6355648; (2002); B1;,
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Reference of 1953-99-7, A common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, molecular formula is C8Cl4N2, 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.

3,4,5,6- tetrachloro phthalo nitrile 0.1 mol anddiethylmalonate 0.1 mol, and potassium carbonate 0.1 mol were stirred withdimethylformamide 60 g at 60 for3~4 hours. Afterthe reaction was complete, the reaction solution was cooled down atroom temperature. The reaction solution was added to water 250 g to crystallizeitself. Thecrystals were filtered under reduce pressure and were dispersedly filtered inthe mixed solution of methanol 50g and water 50g for 1 hour. The crystals were suction filteredand vacuum dried at 60 toobtain [formulaf] compound 30g.

The synthetic route of 1953-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyung-In Synthetic Corporation; Park, Soon Hyeon; Kim, Jeong Ki; Kim, Jeong Rok; Lee, Yun Ah; Lee, Do kyeong; Lee, Min Jeong; Lee, Hui Jae; (16 pag.)KR2016/7024; (2016); A;,
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Electric Literature of 22364-68-7, 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. 22364-68-7 name is 2-(o-Tolyl)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.

EXAMPLE 5; Preparation of(Z)-2-(2-Methyl-phenyl)-3-(1H-pyrrol-2-yl)acryIonitrile Under High PressureA thick walled tube was charged with 1 H-pyrrole-2-carbaldehyde (2.0 g, 21.0 mmol), 2-methylphenyIacetonitrile (2.5 g, 18.9 mmol, 0.9 equivalents), ethanol (75 ml), and 40% aqueous Triton B (4.0 ml, 3.3 mmol). The tube was EPO sealed and heated to 90 0C for 4 days. Removal of the solvent, followed by chromatography on silica gel using dichloromethane/petroleum spirits (20:80) as eluant afforded a yellow solid (1.2 g). This is Compound 16 in Table 8.

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

Reference:
Patent; SCHERING-PLOUGH LTD.; WO2006/55565; (2006); A2;,
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Related Products of 610-66-2,Some common heterocyclic compound, 610-66-2, name is 2-(2-Nitrophenyl)acetonitrile, molecular formula is C8H6N2O2, 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: To a solution of the correspongding catalyst 4k (5 mol%), K2CO3 (2 equiv) and 2-(2-nitrophenyl)acetonitrile (0.10 mmol) in CH2Cl2 (1.0 mL), and then was cooled to -20 C before the imines (0.12 mmol) was introduced. When the reaction was finished (determined by TLC analysis), the crude mixture was warmed to room temperature and purified by flash column chromatography (silica gel: petroleum ether/AcOEt = 5:1) to afford the products

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(2-Nitrophenyl)acetonitrile, its application will become more common.

Reference:
Article; Pan, Renming; Zhang, Jiaxing; Zheng, Changwu; Wang, Hongyu; Cao, Dongdong; Cao, Weiguo; Zhao, Gang; Tetrahedron; vol. 73; 17; (2017); p. 2349 – 2358;,
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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. 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 906673-45-8

Compound IV (1.00 g, 3.3 mmol, 1.0 eq) was dissolved in DMF (15 mL), 60% sodium hydride (0.16 g, 4.0 mmol, 1.2 eq) was added, and stirred at room temperature for 30 min. 2,3,4-Trimethoxybenzyl chloride (1.00 g, 4.6 mmol, 1.4 eq) was added, and the reaction was stirred by heating to 85 C. After 6h, TLC showed that the basic reaction of the raw materials was completed, post-processing was carried out, and the reaction solution was cooled to room temperature. The reaction mixture was quenched by adding 20 mL of water, extracted with 50 mL EA, liquid separation was carried out, the organic phase was washed, dried, concentrated and the crude product was purified by column chromatography to give 1.46 g of yellow oil. That is, the target compound, the yield was 76%.

The synthetic route of 906673-45-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Wangshanwangshui Bio-pharmaceutical Co., Ltd.; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute Suzhou Pharmaceutical Chuangxin Institute; Shandong Tefaman Pharmaceutical Co., Ltd.; Tian Guanghui; Wu Jianzhong; Yu Jianghui; Pang Zhenqiang; Li Junyong; (10 pag.)CN108047261; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 29509-06-6, name is 4-Methyl-3-oxopentanenitrile, 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 29509-06-6, Quality Control of 4-Methyl-3-oxopentanenitrile

A mixture of a portion (0.6 g) of the material so obtained, hydrazine hydrate (0.288 ml) and ethanol (45 ml) was heated at 700C for 12 hours. The solvent was evaporated and the residue was purified by column chromatography on silica using a 19:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the required starting material (0.574 g); 1H NMR: (DMSOd6) 1.13 (d, 6H), 2.76 (m, IH), 4.31 (br s, 2H), 5.17 (br s, IH), 11.05 (br s, IH); Mass Spectrum: M+H+ 126.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/99317; (2007); A1;,
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Related Products of 60899-34-5,Some common heterocyclic compound, 60899-34-5, name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, molecular formula is C10H7NO, 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 stirred mixture of 1 -oxo-2,3 -dihydro- 1 H-indene-4-carbonitrile (mt 1) (20.Og, 98 wt%, 18.6 assay g, 124.8 mmol) in abs EtOH (20 mL), triethylorthoformate (80 mL, 481 mmol) and methanesulfonic acid (0.88 mL, 12.5 mmol) in toluene (80 mL)was heated at 43 -47C. After 1 h, GC analysis showed orthoformate consumed and 12.8 area% of mt 1 remaining. A further charge of triethylorthoformate (20 mL, 120.2 mmol) was made and after 45 mm GC analysis showed 1.5 area% mt 1. The batch was cooled to ambient temperature and then poured into 1 M aq. K2HPO4 (200 mL) with vigorous stirring while maintaining a quench temperature < 15 C. The two-phasemixture was vigorously stirred for 10 mm. The phases were separated and the aqueous phase (pH 11) was back extracted with toluene (100 mL). The organic phases were combined and distilled at atmospheric pressure to remove 340 mL distillate. Toluene was added (500 mL) and distilled at atmospheric pressure to remove 500 mL distillate. Total distillation time 3 h, temperature range 80-120 C. At this point the batch wasstored overnight at < 5 C. Excess orthoformate was removed by chasing with ethyl acetate (100 mL) under reduced pressure until distillation stopped. Another volume of ethyl acetate (100 mL) was added and then concentrated under reduced pressure until distillation stopped. A third volume of ethyl acetate (100 mL) was added and then concentrated under reduced pressure until distillation stopped, after which GC analysisconfirmed no orthoformate remaining. The crude was then stirred at 110 C for 1 h, to convert the intermediate ketal to 3-ethoxy-1H-indene-7-carbonitrile (mt 2). Upon cooling, the crude (mobile oil, 21.34 g) was assayed for mt 2 by ?H NIVIR employing mesitylene as an internal standard. The oil assayed at 78.1 wt% product = 16.73 assay g, 90.0 mmol = 72.1 % assay yield. The crude oil was then purified by filtration througha silica gel plug eluting with 15% EtOAc/hexane. The pure fractions were combined and utilized for the next step. ?H NIVIR (400 MHz, d6-DMSO) 7.78 (d, J = 8.4, 1H), 7.63 (m, 1H), 7.49 (m, 1H), 5.60 (m, 1H), 1.38 (t, J= 6.8 Hz, 1H), 1.19 (t, J= 6.8 Hz, 1H); LRMS: calcd for C,2H,2NO [M + H]: 186.2; Found: 186.2. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, its application will become more common. Reference:
Patent; CELGENE INTERNATIONAL II SARL; MEADOWS, Kristen, R., Taylor; SKOLNICK, Brett; DALVIE, Deepak; (78 pag.)WO2018/208855; (2018); A1;,
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Related Products of 67515-59-7, A common heterocyclic compound, 67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, molecular formula is C8H3F4N, 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.

4-fluoro-3-(trifluoromethyl)benzonitrile (1 g; 5.29 mmol; 1 eq.) and (S)-(+)-2-methylpiperidine (3.1 ml 26.4 mmol; 5 eq.) in DMSO (10 ml.) were heated at 10O0C under nitrogen for 12h. The reaction mixture was then diluted in EtOAc, washed with water, NaHCO3 sat and NH4CI sat. The organic phase was dried over MgSO4, filtered and evaporated under vacuum to give a yellow oil, that was submitted to the next step without further purification. LC/MS (Method B): 269.0 (M+H)+.

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; MERCK SERONO S.A.; MUZERELLE, Mathilde; QUATTROPANI, Anna; MONTAGNE, Cyril; DORBAIS, Jerome; WO2010/69949; (2010); A1;,
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Electric Literature of 72291-30-6, The chemical industry reduces the impact on the environment during synthesis 72291-30-6, name is Methyl 2-cyano-2-methylpropanoate, I believe this compound will play a more active role in future production and life.

A mixture of cyano-dimethyl-acetic acid methyl ester (5 g, 39.4 mmol), Boc anhydride (17.2 g, 78.7 mmol), and NiCl2 (0.51 g, 3.94 mmol) in MeOH (200 mL) was cooled in an ice bath. NaBH4 (10.4 g, 276 mmol) was slowly added over 1 h at 0C, and the resulting mixture was stirred at r.t. for 16 h. Diethylenetriamine (4.3 mL, 39.4 mmol) was then added, and the mixture was stirred for 30 min. The solvent was evaporated, and the residue was partitioned between EtOAc (200 mL) and saturated NaHCC>3 (400 mL). The aqueous layer was extracted with additional EtOAc, and the organic layers were combined, dried over MgSO/t, and concentrated. The crude product was purified by column chromatography (0-40% EtOAc/hexanes) to give 2.5 g of the title compound as a clear oil. H NMR (CDCI3, 200 MHz): 8ppm= 4.95 (br s, 1H), 3.69 (s, 3H), 3.24 (d, 2H, J= 6.6 Hz), 1.44 (s, 9H), 1.20 (s, 6H).

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 2-cyano-2-methylpropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FIBROGEN, INC.; HO, Wen-Bin; ZHAO, Hongda; DENG, Shaojiang; NG, Danny; WRIGHT, Lee R.; WU, Min; ZHOU, Xiaoti; AREND, Michael P.; FLIPPIN, Lee A.; WO2013/134660; (2013); A1;,
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