Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 19924-43-7, name is 2-(3-Methoxyphenyl)acetonitrile, 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 19924-43-7, Safety of 2-(3-Methoxyphenyl)acetonitrile

Example 1 Intermediate 1 3-(3,4-dimethylphenyl)-2-(3-methoxyphenyl)propanal To a solution of 3,4-dimethylbenzaldehyde (CAS 68844-97-3) (4.0 g, 29.6 mmol) and 3-methoxybenyl)acetonitrile (CAS 19924-43-7) (4.35 g, 29.6 mmol) in absolute EtOH, 30 mL, was added NaOMe (0.1 equiv), the mixture was stirred at room temperature for 2 h. Then, the reaction mixture was cooled to 0C and filtered. The precipitate was washed with cold EtOH and gave (2E)-3-(3,4-dimethylphenyl)-2-(3- methoxyphenyl)acrylonitrile as a white solid (6.20 g, 78%). NaBH4 (1 .8 g, 47 mmol) was added slowly to the solution of (2E)-3-(3,4- dimethylphenyl)-2-(3-methoxyphenyl)acrylonitrile (6.17 g, 23.5 mmol) in EtOH (100 mL) under argon. The mixture was stirred at 70C for 16 h. The solution was cooled to room temperature and quenched with water. The reaction mixture was diluted with 100 mL water and acidified with 6M HCI (aq.). After extraction with ether (3 x 100 mL), the combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated to get 3-(3,4-dimethylphenyl)-2-(3- methoxyphenyl)propanenitrile as a white solid (6 g, 96 %). DIBAL-H (1 .0 M in toluene, 14 mL, 14 mmol) was added dropwise to the solution of 3-(3,4-dimethylphenyl)-2-(3-methoxyphenyl)propanenitrile (2.93 g, 1 1 .72 mmol) in Toluene (40 mL) at -78C under argon. The mixture was stirred at -78C to -20C for 3h and then quenched by slow addition of saturated NH4CI solution (2 mL) followed by Celite (2g) at -20C. The mixture was diluted with Et2O (50 mL), warmed slowly to room temperature, and stirred till all aluminum precipitated. The solid was filtered and washed with ether (3 x 50 mL), the combined organic layers wer dried over MgSO , filtered and concentrated and gave Intermediate 1 (2.34 g, 74 %).1 H NMR (CDCI3, 300 MHz) delta: 9.72 (d, J = 1 .8 Hz, 1 H), 7.21 – 7.34 (m, 1 H), 6.98 (d, J = 7.3 Hz, 1 H), 6.74 – 6.92 (m, 4H), 6.70 (s, 1 H), 3.69 – 3.89 (m, 4H), 3.40 (dd, J = 14.1 , 7.3 Hz, 1 H), 2.92 (dd, J = 14.1 , 7.3 Hz, 1 H), 2.20 (d, 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, 2-(3-Methoxyphenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALLERGAN, INC.; SINHA, Santosh C.; BHAT, Smita S.; CORPUZ, Evelyn G.; CHOW, Ken; FANG, Wenkui K.; IM, Wha Bin; WO2012/74921; (2012); A1;,
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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. 60710-80-7, name is 3-Amino-4-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: nitriles-buliding-blocks

(Boc)20 (50 g, 227 mmol) was added portion-wise to a stirred solution of 3-amino-4- methylbenzonitrile (7) (10 g, 75.7 mmol) and DMAP (0.5 g) in THF (250 ml_). After 30 minutes, the reaction was heated at 60 C overnight. The crude reaction mixture was purified over silica gel to obtain a white solid tert-butyl 5-cyano-2-methylphenylcarbamate (34) (17.5 g, quantitative yield). MS m/z 233.1 (M+1 )+. NH2OH (20 ml_, 50% in water) was added to a stirred solution of tert-butyl 5-cyano-2- methylphenylcarbamate (34) (17.5 g, 75.3 mmol) in EtOH (200 ml_) and the resulting solution was heated at 50 C for 10 hours. The solvent was then evaporated and the product was titurated with EtOAc and hexane to obtain a white solid (Z)-tert-butyl 5-(N’- hydroxycarbamimidoyl)-2-methylphenylcarbamate (35) in a quantitative yield which was used without further purification. MS m/z 266.1 (M+1 )+.

The synthetic route of 60710-80-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; LIU, Xiaodong; LI, Xiaolin; LOREN, Jon; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; YEH, Vince; WO2013/33116; (2013); A1;,
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Related Products of 194853-86-6, These common heterocyclic compound, 194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, 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.

A solution of 4-fluoro-2-(trifluoromethyl)benzonitrile (7.00 g, 37.1 mmol), tert- butyl N-(5-aminopentyl)carbamate (10 g, 49.43 mmol), and Nu,Nu-diisopropylethyl amine (11 g, 85.11 mmol) in DMF (100 mL) stirred for 6 h at room temperature. The resulting solution was diluted with 400 mL of ethyl acetate, washed with 2x200mL brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography with silica gel (eluting with ethyl acetate/petroleum ether (1 : 1)) to give tert- butyl 5-(4-cyano-3-(trifluoromethyl)phenylamino)pentylcarbamate (11 g, 60%) as colorless oil. MS: (ESI, m/z): 372[M+H]+.

Statistics shows that 4-Fluoro-2-(trifluoromethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 194853-86-6.

Reference:
Patent; FORMA THERAPEUTICS, INC.; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; LEE, Jennifer; BURNETTE, Pearlie; CHELLAPPAN, Srikumar; BARCZAK, Nicholas; CONTI, Chiara; ESCOBEDO, Jaime A.; HAN, Bingsong; LANCIA, David R., Jr.; LIU, Cuixian; MARTIN, Matthew W.; NG, Pui Yee; RUDNITSKAYA, Aleksandra; THOMASON, Jennifer R.; ZHENG, Xiaozhang; (322 pag.)WO2018/75959; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 31643-49-9, name is 4-Nitrophthalonitrile, 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 31643-49-9, category: nitriles-buliding-blocks

10 g of 2-mercaptopyridine, 14.2 g of 4-nitrophthalonitrile, and 22.6 g of potassium carbonate were suspended in 250 ml of acetone and heated at reflux temperature for 4 hours. The solution was filtered through a pad of celite and a course glass filter to remove residual solids. The solution was concentrated to a crude residue and purified by column chromatography on silica gel eluting the product with a gradient of 0-10% ethyl acetate in dichloromethane. 6.4 g of product was recovered; 1H NMR (200 Mz, CDCl3) delta=8.49-8.53 (m, 1H), 7.84-7.83 (dd, 1H), 7.76-7.71 (m, 2H), 7.68-7.64 (dd, 1H), 7.40-7.36 (dt, 1H), 7.27-7.20 (m, 1H).

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-Nitrophthalonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FibroGen, Inc.; US2004/254215; (2004); A1;,
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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. 455-18-5, name is 4-(Trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-(Trifluoromethyl)benzonitrile

N-Hydroxy-4-trifluoromethylbenzimidamide (47c). 4-Trifluoromethylbenzonitrile 46c (1.37 g, 8.0 mmol) in ethanol (30 mL) was added to hydroxylamine hydrochloride (3.34 g, 48 mmol) and sodium hydrogen carbonate (2.54 g, 24 mmol) in water (30 mL) and the mixture was stirred at 100C for 3 h. The ethanol was evaporated from the cooled mixture and the residue was poured into ice-cold water. The precipitate was collected by filtration, washed (water) and dried to give N-hydroxy-4-trifluoromethyl- benzimidamide 47c (1.60 g, 98%) as a white powder: 1 18-120C (lit.95 128-129C); 1H NMR ((CD3)2SO) delta 6.01 (2 H, br, NH2), 7.79 (2 H, d, J = 8.4 Hz, Ph 2,6-H2), 7.94 (2 H, d, J = 8.4 Hz, Ph 3,5-H2), 9.96 (1 H, s, OH); 13C NMR ((CD3)2SO) delta 124.98 (q, J = 3.1 Hz, 3,5-C2), 125.54 (q, J = 331 Hz, CF3), 126.05 (2,6-C2), 129.17 (1 -C), 137.28 (q, J = 28 Hz, 4-C), 149.76 (C=N); 19F NMR (CDCI3) delta -62.84 (CF3); MS m/z 205.0610 (M + H)+ (C8H8N2OF3 requires 205.0589).

The synthetic route of 455-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF BATH; THREADGILL, Michael David; LLOYD, Matthew David; THOMPSON, Andrew Spencer; NATHUBHAI, Amit; WOOD, Pauline Joy; PAINE, Helen Angharad; KUMPAN, Ekaterina; SUNDERLAND, Peter Thomas; CHUE YEN WOON, Esther; WO2014/87165; (2014); A1;,
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Synthetic Route of 120351-94-2,Some common heterocyclic compound, 120351-94-2, name is 3-(2-Aminoethoxy)benzonitrile, molecular formula is C9H10N2O, 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 1 Synthesis of N-[2-(3-cyanophenoxy)ethyl]-(1R)-10-camphorsulfonamide: The title compound was obtained from 700 mg (4.32 mmol) of 3-(2-aminoethoxy)benzonitrile and 1.08 g (4.32 mmol) of (1R)-(-)-10-camphorsulfonyl chloride in the same manner as that of step 1 in Example 106. Yield: 1.33 g (3.54 mmol) (82 %) MS (ESI, m/z) 377 (MH+)

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

Reference:
Patent; Ajinomoto Co., Inc.; EP976722; (2000); A1;,
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Synthetic Route of 95-11-4, 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. 95-11-4 name is 5-Norbornene-2-carbonitrile, 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.

Ortho-dichlorobenzene (958 g) was added into a five-neck flask which is equipped with a reflux cooling tube,stirring blades, a thermometer, a gas-blowing tube and a raw material-injecting tube, and had an inner volume of 2 liter,154.2 g (1.0 mol) of 2,5-bisaminomethyl-bicyclo[2.2.1]heptane and 2,6-bisaminomethyl-bicyclo[2.2.1]heptane which hadbeen obtained in Example 2 and ortho-dichlorobenzene (702 g) were prepared in a raw material tank. Next, a reactioncontainer was heated to 120C at 0.1 MPa, adding of hydrochloric acid gas from a hydrochloric acid-blowing tube at arate of 43.8 g/hr and adding of an amine diluted by a solvent from the raw material tank using a raw material-injectingpump at a rate of 428.1 g/hr were initiated at the same time, and the total amount was added over 2 hours. Furthermore,aging was carried out for 1 hour while adding hydrochloric acid gas at 20 g/hr. After the completion of the reaction,subsequently, hydrochloride reaction mass was heated to 160C, phosgene was blown in from a phosgene-blowingtube at 100 g/hr (1.0 mol/hr), and a reaction was caused for 6 hours while maintaining the temperature. After thecompletion of the reaction, unreacted phosgene and hydrochloric acid gas in the system were purged using nitrogen,and the solvent was removed, thereby obtaining a solution (200.9 g) including 2,5-bisisocyanate methyl-bicyclo[2.2.1]heptane and 2,6-bisisocyanate methyl-bicyclo[2.2.1]heptane. Furthermore, distillation was carried out under reducedpressure, and a mixture (175.7 g) of 2,5-bisisocyanate methyl-bicyclo[2.2.1]heptane and 2,6-bisisocyanate methylbicyclo[2.2.1]heptane having a purity of 99.0% was obtained. An 1H-NMR chart is illustrated in Fig. 3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Norbornene-2-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Mitsui Chemicals, Inc.; KUMA, Shigetoshi; SAKATA, Michiharu; TOKUNAGA, Kouichi; SHIMAKAWA, Chitoshi; KAKINUMA, Naoyuki; FURUYA, Masayuki; TANAKA, Mamoru; EP2708527; (2014); A1;,
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Electric Literature of 76469-88-0, A common heterocyclic compound, 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, molecular formula is C10H9NO2, 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 1; Methyl 4-(cyanomethyl)benzoate (1.8 g, 10 mmol, 1 eq) was dissolved in THF (100 mL) and cooled to 0C. Sodium hydride (60% w/w in mineral oil, 820 mg, 20 mmol, 2 eq) was added portionwise and the mixture was stirred for 10 minutes. Methyl iodide (1.3 mL, 20 mmol, 2 eq) was added dropwise and the reaction was stirred at 0C until the starting material was consumed by TLC (2 hours). The reaction mixture was quenched with water and was partitioned between EtOAc and brine. The aqueous layer was discarded, and the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated to afford a crude residue which was chromatographed on silica gel (gradient elution, 0% to 50% EtOAc in hexanes, Si02) to afford the desired product as a white crystalline solid (1.88g, 74%).

The synthetic route of 76469-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WONG, Michael, K.; LAVEY, Brian, J.; YU, Wensheng; KOZLOWSKI, Josheph, A.; DEMONG, Duane, E.; DAI, Xing; STAMFORD, Andrew, W.; MILLER, Michael, W.; ZHOU, Guowei; YANG, De-Yi; GREENLEE, William, J.; WO2011/119559; (2011); A1;,
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Reference of 1187-42-4,Some common heterocyclic compound, 1187-42-4, name is Diaminomaleonitrile, molecular formula is C4H4N4, 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: AlCl3 (15 molpercent) was added to a solution of DAMN (1 mmol), ketone (1 mmol) and isocyanide (1 mmol), in 5 ml of CH3CN. The resulting mixture was stirred for an appropriate time at room temperature. After completion of the reaction, as indicated by thin-layer chromatography (TLC; ethyl acetate=n-hexane 3=1), the product was precipitated by addition of 10 ml of water. The precipitate was filtered off, washed with water, and then recrystallized from acetone. In the case of aromatic aldehyde, precipitate after filtration was loaded on column chromatography with 20percent ethyl acetate?hexane as an eluent system to furnish the product.

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

Reference:
Article; Bhosale, Shrikar M.; Naik, Nilesh H.; Kusurkar, Radhika S.; Synthetic Communications; vol. 43; 23; (2013); p. 3163 – 3169;,
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Reference of 19472-74-3,Some common heterocyclic compound, 19472-74-3, name is 2-Bromophenylacetonitrile, molecular formula is C8H6BrN, 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 100 mL round bottom flask was evacuated and back-filled byargon 3 times, and charged with 0.84 mL of o-bromophenylacetonitrile(6.5 mmol) and 25 mL of toluene under a positive pressure ofargon. After being cooled in an ice bath for 5 min, 7.5mL of a solutionof NaHMDS in THF (1 M, 7.5 mmol) was added to this toluenesolution, and the ice bath was removed. After 30 min, 0.47mL of 2-chloropyridine (5.0 mmol) was added, and the mixture was heatedin a 70 C oil bath for 6 h. The progress of reactionwas monitored byTLC. Upon completion, reaction was quenched by adding 50 mL ofsaturated aqueous ammonium chloride solution reaction, then extracted by 30 mL of ethyl acetate for three times. The combinedorganic extract was dried (anhydrous sodium sulfate), filtered(celite plug), and concentrated under a reduced pressure. A silicagel column chromatography purification (9:1 Hexanes/EtOAc)afforded 0.84 g of 1h in 64% yield.1h: 1H NMR (400 MHz, CDCl3) delta ppm 8.63-8.62 (1H, m),7.70-7.59 (m, 3H), 7.59e7.35 (m, 1H), 7.38-7.20 (m, 3H), 5.80 (s,1H). 13C NMR (101 MHz, CDCl3) delta ppm 153.95, 150.23, 137.38, 134.17,133.40, 130.44, 130.26, 128.40, 123.70, 123.27, 122.51, 118.53, 44.74.13C-DEPT 135 NMR (101 MHz, CDCl3) delta ppm 150.23, 137.37, 133.39,130.43, 130.24, 128.39, 123.26, 122.50, 44.72.

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

Reference:
Article; Chuentragool, Padon; Li, Zhou; Randle, Katrina; Mahchi, Faraj; Ochir, Ishmael; Assaf, Shadi; Gevorgyan, Vladimir; Journal of Organometallic Chemistry; vol. 867; (2018); p. 273 – 277;,
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