Tag: M.W=0-100

Reference of 4426-11-3, These common heterocyclic compound, 4426-11-3, name is Cyclobutanecarbonitrile, 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.

[00140] To a mixture of cyclobutanecarbonitrile (0.70 g, 8.6 mmol) and 2-chloro-6- fluorobenzoic acid (0.5 g, 2.9 mmol) in THF (9.6 mL) at 0 C was added KHMDS (0.5M in toluene, 12.6 mL, 6.3 mmol). The resulting mixture was heated at 70 C for 3h, then cooled down, concentrated in vacuo. The residue was taken up in 20mL H20, and extracted with Et^O for three times. The aqueous layer was acidified with 2N HC1, and extracted with CHCI3/1- PrOH (3: 1). The combined organics were dried over Na2SC>4, concentrated. The crude residue was used directly. MS: 236 (M+l). XH NMR (600 MHz, DMSO-d6): delta 12.9-13.1 (brs, 1H), 7.51 (dd, 1H, J= 8.4, 1.2Hz), 7.46 (t, lH, J= 8.4 Hz), 7.30 (dd, 1H, J= 8.4, 1.2 Hz), 2.56- 2.68(m, 4H), 2.22-2.32 (m, 1H), 1.84-1.90 (m, 1H).

The synthetic route of 4426-11-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LAPOINTE, Blair, T.; FULLER, Peter, H.; GUNAYDIN, Hakan; LIU, Kun; SCOTT, Mark, E.; TROTTER, B., Wesley; ZHANG, Hongjun; (211 pag.)WO2017/75182; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2469-99-0, name is 3-Oxobutanenitrile, 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 2469-99-0, Safety of 3-Oxobutanenitrile

In a 250 mL RBF, 3-aminobut-2-enenitrile (2.0 g, 0.24 mole) was added to a stirred solution of cyclohexyl hydrazine hydrochloride (4.0 g, 0.026 mole) and acetic acid (0.1 mL) in ethanol (60 mL). The reaction was refluxed for 6 h. Crude was evaporated and loaded on column to elute out product at 40% ethyl acetate in hexane. (1.74 g, 40%) LCMS: RT = 1.50 min., >98% 215 and 254 nm, m/z = 180.1 [M + H]+. 1H NMR (499 MHz, DMSO) delta 5.02 (s, 1H), 4.92 (s, 2H), 3.86 – 3.78 (m, 1H), 1.94 (s, 3H), 1.78 – 1.68 (m, 4H), 1.63 (dd, J = 16.3, 7.4 Hz, 3H), 1.31 (q, J = 12.9 Hz, 2H), 1.18 – 1.08 (m, 1H). 13C NMR (126 MHz, DMSO) delta 145.90, 144.64, 87.80, 53.50, 32.13, 25.21, 25.05, 14.02.

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

Reference:
Article; Sharma, Swagat; Kozek, Krystian A.; Abney, Kristopher K.; Kumar, Sushil; Gautam, Nagsen; Alnouti, Yazen; David Weaver; Hopkins, Corey R.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 6; (2019); p. 791 – 796;,
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Adding a certain compound to certain chemical reactions, such as: 19295-57-9, name is 3-Hydroxy-2,2-dimethylpropanenitrile, 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 19295-57-9, Formula: C5H9NO

A solution of 60% sodium hydride (367.1 mg, 15.3 mmol) was washed with hexane (3x 2 ml) and suspended in DMF (2 ml). The suspension was cooled to -10C and then a mixture of 3-hydroxy-2,2-dimethylpropanenitrile (1.4 g, 13.9 mmol) and DMF (8 ml) was added. The mixture was cooled 2.5 hour with stirring stirred at -10 to -5C and then benzyl bromide (1.7 ml, 13.9 mmol) was added. The mixture was cooled 2 hours with stirring at -5C, diluted with water (10 ml) and extracted with diethyl ether (3x 10 ml). The combined extracts were washed with water (1x 10 ml) and brine (1x 10 ml), dried (MgSO4) and concentrated to give 3-benzyloxy-2,2-dimethylpropanenitrile (2.5 g, 13.2 mmol).

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; F. HOFFMANN-LA ROCHE AG; EP748800; (1996); A3;,
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Adding a certain compound to certain chemical reactions, such as: 630-18-2, name is Pivalonitrile, 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 630-18-2, Application In Synthesis of Pivalonitrile

A 102 ml (0.407 mol) portion of 4 N hydrochloric acid dioxane solution was added under ice-cooling to a 13.2 ml (0.326 mol) methanol solution of 30.0 ml (0.271 mol) of trimethylacetonitrile and stirred at room temperature for 7.5 hours, and then the reaction solution was concentrated under a reduced pressure. Ether (100 ml) and n-hexane (50 ml) were added to the thus obtained residue, and the precipitated crystals were collected by filtration and dried to obtain 8.06 g (20%) of the title compound as a colorless solid. 1H-NMR (CDCl3)delta: 1.25 (9H, s), 4.10 (3H, s), 11.2 (2H, brs).

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; DAIICHI PHARMACEUTICAL CO., LTD.; EP1717238; (2006); A1;,
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Synthetic Route of 4426-11-3, 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. 4426-11-3, name is Cyclobutanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

LiHMDS (1M in toluene, 17.7 mL, 17.7 mmol, 3.1 eq) is added dropwise to a cold (-5 C.) solution of 4-bromo-2-fluoro-pyridine [Marsais, F. et al, Journal of Organic Chemistry, (1992), 57, 565-573] (1 g, 5.7 mmol) and cyclobutanecarbonitrile (1.39 g, 17.1 mmol, 3 eq) in toluene (20 mL). The reaction mixture is allowed to warm to rt, stirred for 5 h, quenched by addition of a saturated solution of NaHCO3 and filtered through a pad of celite. The filtrate is extracted with EtOAc. The organic phase is washed with a saturated solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (Hex/EtOAc, 1:0?95:5) to afford 933 mg of the title compound as a yellow oil: ESI-MS: 237.0/239.0 [M+H]+; tR=4.27 min (System 1); TLC: Rf’0.30 (Hex/EtOAc, 9:1).

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

Reference:
Patent; Novartis AG; US2009/163469; (2009); A1;,
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Application of 6330-25-2, 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. 6330-25-2, name is 2-Cyano-N-methyl-acetamide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Pyridine was added dropwise with stirring to cyanoacetamide 2a-e(15 mmol) in a round-bottom flask until complete dissolution of the cyanoacetamide. DMAP (18 mg, 0.15 mmol) and mercaptoacetic acid (3.2 ml, 46mmol) were added to the obtained solution. The obtained mixture was refluxed for 12 h in a flask equipped with a reflux condenser,then diluted with 0.5 HCl solution (5 ml).The precipitate of 1,3-thiazolidinone 1 was filtered off and washed with hot MeCN (15 ml). When necessary, the product was additionally purified by refluxing a suspension of thiazolidine in MeCN, followed by hot filtration.(2Z)-N-Methyl-2-(4-oxo-1,3-thiazolidin-2-ylidene)acetamide (1a). Yield 1.37 g (53%), white powder, mp 238-243(decomp.). IR spectrum, nu, cm-1: 1184, 1299, 1398,1415, 1470, 1556 (C=), 1624 (C=O), 1699 (C=O), 3312 (NH). 1H NMR spectrum, delta, ppm (J, Hz): 2.58 (3H, d, J= 4.8, CH3); 3.61 (2H, s, CH2); 5.55 (1H, s, CH); 7.61 (1H, br. s, NH); 11.20 (1H, s, NH). 13C NMR spectrum, delta, ppm: 25.3; 31.9; 92.4; 151.4; 167.0; 174.0. Mass spectrum, m/z(Irel, %): 172 []+(94), 142 [-NHCH3]+(100), 114 [-NHCH3-CO]+(55), 98 (30), 86 (37), 68 (78), 42 (35), 40 (22). Found, %: C 41.70; H 4.61; N 16.51. C6H8N2O2S. Calculated, %: C 41.85; H 4.68; N 16.27

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

Reference:
Article; Obydennov, Konstantin L.; Galushchinskiy, Aleksei N.; Kosterina, Marya F.; Glukhareva, Tatiana V.; Morzherin, Yuri Yu.; Chemistry of Heterocyclic Compounds; vol. 53; 5; (2017); p. 622 – 625; Khim. Geterotsikl. Soedin.; vol. 53; 5; (2017); p. 622 – 625,4;,
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Synthetic Route of 4426-11-3, 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. 4426-11-3, name is Cyclobutanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

LiHMDS (1M in toluene, 17.7 mL, 17.7 mmol, 3.1 eq) is added dropwise to a cold (-5 C.) solution of 4-bromo-2-fluoro-pyridine [Marsais, F. et al, Journal of Organic Chemistry, (1992), 57, 565-573] (1 g, 5.7 mmol) and cyclobutanecarbonitrile (1.39 g, 17.1 mmol, 3 eq) in toluene (20 mL). The reaction mixture is allowed to warm to rt, stirred for 5 h, quenched by addition of a saturated solution of NaHCO3 and filtered through a pad of celite. The filtrate is extracted with EtOAc. The organic phase is washed with a saturated solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (Hex/EtOAc, 1:0?95:5) to afford 933 mg of the title compound as a yellow oil: ESI-MS: 237.0/239.0 [M+H]+; tR=4.27 min (System 1); TLC: Rf’0.30 (Hex/EtOAc, 9:1).

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

Reference:
Patent; Novartis AG; US2009/163469; (2009); A1;,
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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 98730-77-9 as follows. Recommanded Product: 98730-77-9

Step 2. Preparation of 1-((1,3-dioxoisoindolin-2 yl)methyl)cyclopropanecarbonitrile A solution of 1-(hydroxymethyl)-cyclopropanecarbonitrile (5.52 g, 56.8 mmol), phthalimide (9.20 g, 62.5 mmol), and triphenylphosphine (16.4 g, 62.5 mmol) in THF (550 mL) was treated with DEAD (9.90 mL, 62.5 mmol) and stirred at room temperature for 17 hours. The reaction mixture was then concentrated and the resulting solids were triturated in diethyl ether (150 mL), and collected by filtration. Purification by flash chromatography (SiO2, 0-20% EtOAc in DCM) afforded 1-((1,3-dioxoisoindolin-2-yl)methyl)-cyclopropanecarbonitrile (8.8 g, 38.8 mmol, 68%) as a white solid: LCMS(m/z) 227.0 (MH+), tR=0.66 minute; 1H NMR (300 MHz, CDCl3) delta 7.90 (dd, J=5.4, 3.1 Hz, 2H), 7.77 (dd, J=5.4, 3.1 Hz, 2H), 3.81 (s, 2H), 1.30-1.44 (m, 2H), 1.28 (d, J=3.8 Hz, 2H).

According to the analysis of related databases, 98730-77-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Costales, Abran Q.; Huang, Shenlin; Jin, Jeff (Xianming); Liu, Zuosheng; Pecchi, Sabina; Poon, Daniel; Tellew, John; US2011/52578; (2011); 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. 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 6011-14-9

General procedure: N-protected amino acid was dissolved in dichloromethane (DCM). 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl, 1.3 eq.) and hydroxybenzotriazole (HOBt ·xH2O, 1.3 eq.) were added at 0 C and the mixture was stirred for 50 min, after which thecorresponding amine (1.3 eq.) and N,N-Diisopropylethylamine (DIPEA, 1.3 eq.) were added at 0C. After stirring overnight, the mixture was washed with a 5% potassium sulfate solution(KHSO4), a 5% sodium bicarbonate solution (NaHCO3) and with water. After drying over sodiumsulfate (Na2SO4) and evaporation of the solvent, the residue was purified via columnchromatography.

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 6011-14-9.

Reference:
Article; Silva, Daniel G.; Ribeiro, Jean F.R.; De Vita, Daniela; Cianni, Lorenzo; Franco, Caio Haddad; Freitas-Junior, Lucio H.; Moraes, Carolina Borsoi; Rocha, Josmar R.; Burtoloso, Antonio C.B.; Kenny, Peter W.; Leitao, Andrei; Montanari, Carlos A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5031 – 5035;,
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Synthetic Route of 105-34-0,Some common heterocyclic compound, 105-34-0, name is Methyl 2-cyanoacetate, molecular formula is C4H5NO2, 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: A 10 mL round-bottomed flask was charged with carbonyl compound (1 mmol), active methylene compound (1 mmol), S-4 (12 mg and 20 mol% of the substrates), and water (3 mL). The reaction mixture was stirred at room temperature. The suspension was stirred at room temperature for the lengths of time shown in Table 4. The reaction progress was monitored by thin layer chromatography usingn-hexane-EtOAc (5:1) as eluent. After completing the reaction, the reaction mixture solidified in the round-bottomed flask. The solids were then dissolved in hot ethanol (30 mL). The catalyst was removed by filtration and washed with ethanol. The solid product was obtained after the ethanol was concentrated in vacuo.

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

Reference:
Article; Zhao, Xian-Liang; Yang, Ke-Fang; Zhang, Yan-Ping; Zhu, Ju; Xu, Li-Wen; Chinese Chemical Letters; vol. 25; 8; (2014); p. 1141 – 1144;,
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