Tag: M.W=100-200

Related Products of 3544-25-0,Some common heterocyclic compound, 3544-25-0, name is 2-(4-Aminophenyl)acetonitrile, molecular formula is C8H8N2, 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-Amino-phenyl)-acetonitrile (2 g, 15.1 mmol) and dibenzyl dicarbonate (4.33 g, 15.1 mmol) dissolved in dioxane (16 mL) are stirred for 1 hour at RT. After evaporating the solvent, the product is isolated by flash chromatography (silica gel, 4.5×25 cm, CH2Cl2/MeOH=99:1): white solid (3.82 g, 14.4 mmol; 95%); ES-MS: M-H=265.0; Rf(CH2Cl2/MeOH=95:5)=0.49; HPLC: AtRet=6.32 minutes. 1H-NMR (400 MHz, DMSO-d6): 9.82 (s, 1H, NH), 7.51-7.35 (m, 7H, aryl), 7.26 (d, 8.5 Hz, 2H, aryl), 5.15 (s, 2H, CH2), 3.95 (s, 2H, CH2).

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

Reference:
Patent; Bold, Guido; Floersheimer, Andreas; Furet, Pascal; Imbach, Patricia; Masuya, Keiichi; Schoepfer, Joseph G.; US2005/222171; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 102151-33-7, name is 3-Chloro-4-methoxybenzonitrile, 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 102151-33-7, name: 3-Chloro-4-methoxybenzonitrile

Step 1 To a solution of N,N-diethyl-4-methoxy-2-methylbenzamide (1 g, 4.52 mmol) in THF (9 ml) at -78 C. was added dropwise tert-butyllithium 1.7 M in pentane (3.19 ml, 5.42 mmol) and the solution was stirred for 0.5 h before addition of 3-chloro-4-methoxybenzonitrile (0.757 g, 4.52 mmol) in THF (9 ml). The resulting solution was warmed to rt and stirred for 16 h. The reaction mixture was quenched with water, neutralized with 1 N HCl. The precipitated solid was collected and washed with water to give 3-(3-chloro-4-methoxyphenyl)-6-methoxyisoquinolin-1-ol (1.2 g, 84% yield) as a solid after drying. MS: MS m/z 316.1 (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, 3-Chloro-4-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael; US2013/115190; (2013); A1;,
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Electric Literature of 21803-75-8, 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 21803-75-8 as follows.

To a solution of phosgene (2.3 mL, 20% in toluene) in dry DCM (20 mL) was added a solution of 2-chloro-4-cyanoaniline (367 mg) and DIEA (372 mg) in dry DCM slowly. The resulting mixture was stirred at room temperature for 1 hr prior to evaporation to dryness. The residue was dissolved in DCM (10 mL) to which a solution of compound 1f (Example 1,510 mg) and DIEA (310 mg) in DCM was added. The resulting mixture was stirred overnight at room temperature. Aqueous sodium bicarbonate was added and the mixture was extracted with DCM. The organic phase was dried over MgS04 and evaporated to dryness.

According to the analysis of related databases, 21803-75-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SB PHARMCO PUERTO RICO INC; NEUROCRINE BIOSCIENCES INC; WO2005/63749; (2005); A1;,
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These common heterocyclic compound, 14533-86-9, name is Methyl (E)-2-Cyano-3-phenylacrylate, 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. category: nitriles-buliding-blocks

General procedure: To a solution of 1 (0.10 mmol, 1.0 equiv.), [(TMEDA)Ni(o-tolyl)Cl] (1.6 mg, 0.0050 mmol, 5.0 mol %),and PMePh2 (1.9 L, 0.010 mmol, 10 mol %) in THF (1.0 mL, 0.10 M) under an argon atmosphere was added Et2Zn (1.0 M in hexanes, 0.15 mL, 0.15 mmol, 1.5 equiv) at 0 C. After being stirred the mixture at 30 C for the indicated reaction time judged by TLC analysis, the electrophile (2.0 equiv) was added tothe reaction solution at 30 C unless otherwise noted. The reaction mixture was stirred at the indicated temperature for the indicated reaction time. The reaction was quenched by the addition of sat. aq. NH4Cl.The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organiclayer was washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified byflash column chromatography (hexane/EtOAc or hexane/CH2Cl2/EtOAc) on silica gel to afford corresponding product.

The synthetic route of Methyl (E)-2-Cyano-3-phenylacrylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tsujihara, Tetsuya; Tomeba, Moriho; Ohkubo-Sato, Shigeaki; Iwabuchi, Kyoko; Koie, Rino; Tada, Natsumi; Tamura, Satoru; Takehara, Tsunayoshi; Suzuki, Takeyuki; Kawano, Tomikazu; Tetrahedron Letters; vol. 60; 42; (2019);,
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Some common heterocyclic compound, 5653-62-3, name is 2,3-Dimethoxybenzonitrile, molecular formula is C9H9NO2, 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. Safety of 2,3-Dimethoxybenzonitrile

To a solution of 1,1,1,3,3,3-hexamethyldisilazane (20 g) in dry ether (150 mL) was added 2.4M n-butyllithium in hexane (5 mL). After 10 min at room temperature, 2,3-Dimethoxybenzonitrile (16.3 g) was added in one portion and the mixture was kept at room temperature for 16 h. The reaction mixture was the poured onto excess 3N HCl. The aqueous layer was separated, basified with 50% NaOH and the product was exuacted three times with 10% methanol in methylene chloride. The combined organic extracts were dried over magnesium sulfate and the solvents removed in vacuo to afford 2,3-Dimethoxy-benzamidine as a glassy solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5653-62-3, its application will become more common.

Reference:
Patent; Neurogen Corporation; US5681956; (1997); A;,
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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. 53312-79-1, name is 3-Amino-4-chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Amino-4-chlorobenzonitrile

To a stiired solution of compound IM (1.0 g. 6.57 mmoi) in DMF (20 mL) under argon aimospliere was added potassium ethyl xanthate (2.6 g, 16.44 rnmol) at RT. The reaction mixture was heated to 110 C for 12 h. The progress of the reaction was monitored by TLC. The reaction mixture was acidified with IN HC1 solution (50 mL) to pH~2 to get the solid. The solid was filtered, washed wife -hexane (2 x 20 mL) and dried under reduced pressure to obtain compoimd IN (1.0 g, 5.20 rnmol, 80%) as a brown solid. NMR (400 MHz, CDC3): delta 10.03 (brs, 1H); 7.55 (s, 2H), 7.48 (s, 1H)

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 53312-79-1.

Reference:
Patent; VIAMET PHARMACEUTICALS, INC.; YATES, Christopher, M.; SHAVER, Sammy, R.; HOEKSTRA, William, J.; (455 pag.)WO2017/117393; (2017); A1;,
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17626-40-3, name is 3,4-Diaminobenzonitrile, 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. category: nitriles-buliding-blocks

General procedure: Hydroximoyl chloride 10 (0.16g, 1mmol) was added slowly by small portions to a solution of the appropriate 1,2-diaminobenzene 3 (0.3g, 1.5mmol) in ethanol (5-10mL) at room temperature. The mixture was stirred at reflux for 0.5h followed by an additional hour at room temperature, diluted with water (10mL) and 0.1M aq HCl (5mL). The heterogeneous mixture was stirred for 1h. The precipitate was filtered, washed with water, and recrystallized from iPrOH/H2O.

The synthetic route of 17626-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Stepanov, Andrei I.; Astrat’ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V.; European Journal of Medicinal Chemistry; vol. 94; (2015); p. 237 – 251;,
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Reference of 64248-62-0, These common heterocyclic compound, 64248-62-0, name is 3,4-Difluorobenzonitrile, 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.

Thiomorpholine (4.9 mL, 48.5 mmol) and potassium carbonate (13.4 g, 96.9 mmol) was dissolved in 50 mL DMF and the 3,4-difluorobenzenenitrile (6.7 g, 48.5 mmol) was added. Reaction heated to 100C overnight. Reaction was blown to dryness and residue was taken up in EtOAc and washed with water (2x), brine and then dried over sodium sulfate. Drying agent removed by filtration and then organics concentrated down and residue was recrystallized from hot isopropanol to give 8.74 g of 3-fluoro-4- thiomorpholinobenzonitrile as a light yellow solid. Residue can also be purified through silica gel.

The synthetic route of 64248-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLER, Marvin J.; MORASKI, Garrett; (133 pag.)WO2017/49321; (2017); A1;,
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935-02-4, name is 3-Phenylpropiolonitrile, 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. SDS of cas: 935-02-4

General procedure: To a solution of cyanoacetylenes (0.4mmol) with N-tosylimines (0.2 mmol) in toluene (2 mL) was added Ph3P (0.2mmol). The mixture was then stirred at 110 C for 36 h in a reaction flask. Thenthe solvent was removed in vacuo and residue was purified by columnchromatography on silica gel to give the desired annulation product.

The synthetic route of 935-02-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Jinfeng; Zhang, Qi; Ji, Xin; Meng, Ling-Guo; Synlett; vol. 30; 9; (2019); p. 1095 – 1099;,
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Reference of 874-90-8, These common heterocyclic compound, 874-90-8, name is 4-Methoxybenzonitrile, 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.

Bis(4-methoxyphenyl)methammine (1) was prepared according to the procedure described in Pickert et al., (1973) Organic Syntheses Coll. Fpp520-522 and Dejaegher et al., (2002) Synlett 113-115. Magnesium (0.76 g) was suspended in 30 mL dry THF in a flame-dried 3-neck round-bottomed flask equipped with a stir bar. Some drops of 4-bromoanisole were added, and to initiate the reaction, a crystal of iodine was added and the solution heated to a gentle reflux (-6O0C). Once the color of the iodine had disappeared, the remaining l-bromo-4- methoxybenzene (3.9 mL) in 8 mL THF was added. The mixture was refluxed for 45 minutes. After cooling to RT, 2.5 g of p-methoxybenzonitrile in dry THF was added over 20 minutes and reacted for 6 h under reflux. The reaction mixture was cooled and 4.5 mL of methanol added to quench the reaction. After stirring for 20 minutes, it was concentrated to remove THF, redissolved in CH2Cl2 and quickly washed with water in a separatory funnel to remove Mg salts. The CH2Cl2 layer was dried over MgSO4, concentrated, redissolved in a minimal amount of dichloromethane and diethyl ether added to precipitate white shiny crystals of Bis(4- methoxyphenyl)methanimine (4.01 g, 59% yield). It is worthy of mention that the preparation of this diarylketimine was simple and efficient resulting in crystals without any additional lengthy purification steps such as distillation or chromatography which contributes to the simpler glycosylation chemistry. Rf = 0.32 (60% EtOAc: hexanes), m.p. = 128-129 0C, 1H NMR (CDCl3, 500 MHz) d 3.84 (6H, s), 6.90 (4H, d, J= 9.0 Hz), 7.52 (4H, d, J= 8.5 Hz), 8.95 (NH, broad) ; 13C NMR (CDCl3, 500 MHz) d 55.3 (2CH3O), 113.4 (4CH), 129.98 (4CH), 132.1(2C, q), 161.1 (2C- O, q), and 176.9 (C=N).

Statistics shows that 4-Methoxybenzonitrile is playing an increasingly important role. we look forward to future research findings about 874-90-8.

Reference:
Patent; THE ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA; WO2007/55698; (2007); A1;,
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