Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 42872-73-1, name is 2-Bromo-4-methylbenzonitrile, 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 42872-73-1, Product Details of 42872-73-1

To a stirred solution of lnt4.1 (500 mg) in toluene (7.5 ml) was added 2-bromo-4-methylbenzonitrile (1.2 g), Pd2dba3 (140 mg) and rac-BlNAP (191 mg). The flask was twice degased and backfilled with argon. The mixture was stirred at r.t. for 5 minutes. Caesium carbonate (2.5 g) was added, the flask was twice degased and backfilled with argon and the mixture was heated to reflux for 4h. Further Pd2dba3 (140 mg) and rac-BINAP (191 mg) was added, the flask was twice degased and backfilled with argon and the mixture was heated to reflux for 2h. Water was added and the reaction mixture was extracted with a mixture of dichloromethane and methanol (10:1). The combined organic phases were washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 205 mg of the title compound. 1H-NMR (400MHz, DMSO-d6): delta [ppm]= 1.46 (s, 9H), 2.35 (s, 3H), 6.96 (dd, 1 H), 7.54 (d, 2H), 7.57 – 7.63 (m, 2H), 7.66 (d, 2H), 7.79 (s, 1H), 7.87 (dd, 1H), 9.04 (dd, 1 H), 9.34 (s, 1 H), 9.47 (s, 1 H).

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-Bromo-4-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Schering Pharma AG; EP2343297; (2011); A1;,
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Application of 1885-38-7, 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. 1885-38-7, name is (E)-Cinnamonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Similarly to the above-described, using sodium borohydride (0.4 g, 0.011 mol), 20 mL of isopropanol, anhydrous nickel(II) chloride (0.7 g, 0.006 mol), and cinnamic acid nitrile (6 g, 0.046 mol). The reaction duration was 6 h, the temperature was 70C. 3-Phenylpropionitrile 6e, content 48.9 wt %. Mass spectrum, m/e (Irel, %): 132.0 (10) [M+1], 130.7 (12) [M]+,129.0 (2), 104.0 (2), 91.1 (100), 65.0 (14). Starting cinnamic acid nitrile was also detected in the reaction mixture, its content was of 47.9 wt %.

The synthetic route of (E)-Cinnamonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mokhov; Popov; Shcherbakova; Russian Journal of General Chemistry; vol. 86; 2; (2016); p. 273 – 280; Zh. Obshch. Khim.; vol. 86; 2; (2016); p. 245 – 252,8;,
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Adding a certain compound to certain chemical reactions, such as: 20925-27-3, name is 4-Amino-2-chlorobenzonitrile, 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 20925-27-3, Safety of 4-Amino-2-chlorobenzonitrile

To a stirred solution of 4-amino-2-chlorobenzonitrile (5.02 g, 32.9 mmol) in dichloromethane (80 mL) was added N,N-diisopropylethylamine (17.0 mL, 97.8 mmol) and methanesulfonyl chloride (3.0 mL, 38.8 mmol) at-78 C. The reaction was then allowed to warm to room temperature slowly. After stirring at room temperature for 12 h, the reaction was quenched with 1 N hydrochloric acid. The organic phase was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, 50:50 hexanes/ethyl acetate) to give the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-2-chlorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2005/108382; (2005); A1;,
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Synthetic Route of 4640-66-8, A common heterocyclic compound, 4640-66-8, name is 4-Chlorophenacylcyanide, molecular formula is C9H6ClNO, 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-carbonyl-3-(4-chlorophenyl)propanenitrile (I-c) (180 mg)And thiourea (II) (152 mg) were added to methanol (5 mL) at room temperature.Add to reactionPeroxy tert-butyl alcohol (288 muL)And azobisisobutyronitrile (33mg),Stir at room temperature for 2 hours. After the reaction was completed, saturated aqueous sodium bicarbonate (50 mL) was added.After extraction with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a crude product.The crude product was isolated and purified by column chromatography (ethyl acetate: petroleum ether (v/v) = 3:7).Yielded 191 mg of 2-amino-4-(4-chlorophenyl)-5-carbonitrilethiazole (III-c) as a white solid,Yield: 81%.

The synthetic route of 4640-66-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tianjin University; Du Yunfei; Sun Jiyun; Zhao Kang; (8 pag.)CN107739350; (2018); A;,
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Synthetic Route of 7251-09-4, 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. 7251-09-4, name is 4-Amino-2-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(a) Synthesis of tert-butyl 4-cyano-3-methyl-3-methoxyphenylcarbamate A solution of sodium hydroxide (0.566 g, 14.2 mmol) in water (6 ml) was added to a solution of the 4-amino-2-methoxybenzonitrile obtained in Example 74 (2 g, 13.5 mmol) in a mixture of t-butanol (10 ml) and tetrahydrofuran (3 ml), followed by adding dropwise thereto a solution of di-tert-butyl dicarbonate (3.09 g, 14.2 mmol) in t-butanol (2 ml), and the resulting mixture was stirred at room temperature for 4 days. During the stirring, di-tert-butyl dicarbonate (11.9 g, 54.5 mmol) and sodium hydroxide (2.18 g, 54.5 mmol) were added thereto. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate = 3/1 to 2/1) to obtain tert-butyl 4-cyano-3-methyl-3-methoxyphenylcarbamate (1.87 g, 56%).

The synthetic route of 4-Amino-2-methoxybenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Pharmaceuticals Company, Limited; EP1500643; (2005); A1;,
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Synthetic Route of 591769-05-0, The chemical industry reduces the impact on the environment during synthesis 591769-05-0, name is 3-Cyclopentylacrylonitrile, I believe this compound will play a more active role in future production and life.

To a solution of 4-[3-(fluoromethyl)-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=469[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-Cyclopentylacrylonitrile, other downstream synthetic routes, hurry up and to see.

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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Electric Literature of 1122-85-6,Some common heterocyclic compound, 1122-85-6, name is Phenyl Cyanate, molecular formula is C7H5NO, 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.

EXAMPLE 1 A solution of 2.60 g of 4-(2,2-dibromovinyl)-4′-pentylbiphenyl in 50 ml of absolute tetrahydrofuran was placed at -78 C. in a sulphonation flask under argon gasification and treated within 5 minutes with 14.5 ml of a 1.2N solution of butyl lithium in hexane. After completion of the addition, the mixture was warmed to -10 C. within 10 minutes and then, after renewed cooling to -78 C., treated with a solution of 1.5 ml of phenyl cyanate in 10 ml of absolute tetrahydrofuran. The mixture was subsequently stirred at -78 C. for a further 30 minutes, then poured into 100 ml of water and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed twice with 50 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residue (2.51 g) on silica gel with hexane followed by 2% ethyl acetate/petroleum ether and subsequent recrystallization from methanol gave 1.02 g (58%) of (4′-pentyl-4-biphenylyl)propiolonitrile as colourless crystals (purity 99.6%); m.p. (C-N) 51.0 C., cl.p. (N-I) 120.2 C. The 4-(2,2-dibromovinyl)-4′-pentylbiphenyl used as the starting material was prepared as follows:

The synthetic route of 1122-85-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US4528114; (1985); A;,
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These common heterocyclic compound, 4110-35-4, name is 3,5-Dinitrobenzonitrile, 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. Formula: C7H3N3O4

The 3,5-dinitrobenzonitrile (10 g, 0.052 mol), sodium azide(3.97 g, 0.061 mol) and triethylammonium chloride (8.4 g,0.061 mol) were mixed with DMF (50 mL). The reaction mixturewas heated at 100 C for 6 h. Upon completion, the reaction mixturewas filtered, DMF was evaporated, and the residue was dissolved inwater (100 mL). The solutionwas acidified with HCl to pH 1, and theprecipitated product was filtered, washed with water and dried.Yield: 87% as a yellowish solid, mp: 176-177 C (lit. [27]. 178-179 C). 1H NMR (300 MHz, DMSO-d6) delta 9.13 (dd, J =2.1, 0.5 Hz, 2H),8.96 (td, J = 2.1, 0.5 Hz, 1H). 13C NMR (75 MHz, DMSO) delta 154.92,148.92, 128.05, 126.97, 120.40.

The synthetic route of 3,5-Dinitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; N?me?ek, Jan; Sychra, Pavel; Macha?ek, Miloslav; Benkova, Marketa; Karabanovich, Galina; Kone?na, Klara; Kavkova, V?ra; Stola?ikova, Ji?ina; Hrabalek, Alexandr; Vavrova, Kate?ina; Soukup, Ond?ej; Roh, Jaroslav; Klime?ova, V?ra; European Journal of Medicinal Chemistry; vol. 130; (2017); p. 419 – 432;,
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Related Products of 654-70-6, 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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, This compound has unique chemical properties. The synthetic route is as follows.

Preparation by process ?B?: 14.74 g (79.21 mmol) of 4-amino-2-trifluoromethyl-benzonitrile were dissolved in 200 ml of dry acetonitrile. This solution was added dropwise with stirring to a 20% solution, heated to 70 C., of phosgene in toluene and then stirred for 1 h. The cooled reaction solution was concentrated under reduced pressure, and the residue was taken up with toluene and concentrated again under reduced pressure. Finally, the residue was dissolved in 150 ml of dry acetonitrile and the solution was admixed with stirring with 15.5 g (79.21 mmol) of tert-butyl 2-amino-2-methylpropionate hydrochloride. 12.02 g (118.8 mmol) of triethylamine were slowly added dropwise to the reaction mixture and then it was stirred at room temperature for 45 min. Thereafter, the mixture was admixed cautiously with 50 ml of concentrated hydrochloric acid and stirred at 70 C. for 1 h. The cooled reaction mixture was concentrated under reduced pressure and the residue was admixed with ethyl acetate and water. The organic phase was removed, washed with saturated sodium hydrogencarbonate solution and then with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography using silica gel with 2:1 heptane /ethyl acetate. This afforded 21.2 g (90% yield) of 4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile 1.2 with melting point 208-211 C.

The chemical industry reduces the impact on the environment during synthesis 4-Cyano-3-trifluoromethylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SANOFI-AVENTIS; US2011/178134; (2011); A1;,
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Synthetic Route of 621-50-1, A common heterocyclic compound, 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, molecular formula is C8H6N2O2, 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.

(c) 5-Phenyl-furan-2-carboxylic acid [3-(lH-tetrazol-5- ylmethyl)-phenyl]-amide (75); (i) (3-Amino-phenyl)-acetonitrile (80); A solution of 3-nitrophenyl acetonitrile (500 mg, 3.1 mmol) in 5% AcOH (10 ml) was heated to 80C. Iron powder (1.5 g, 27 mmol) was then added and the resulting mixture stirred for 2 h. The reaction mixture was filtered through celite and the filter cake washed with MeCN (4 x 50 ml). The combined MeCN layers were evaporated in vacuo and the residue was re-dissolved in EtOAc (30 ml) followed by 2M HC1 (30 ml). The aqueous layer was separated, basified to pH 10 with 6M NaOH, and extracted with EtOAc (3 x 80 ml). The combined organic layers were dried (MgSO4), filtered and the solvent removed in vacuo to give the title compound. Yield: 140 mg, 34% ; 1H NMR (400 MHz, CDC13) : 5 3.65 (s, 2H), 3.75 (s, 2H), 6.60-6. 70 (m, 3H), 7.15 (t, 1H)

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; PHARMAGENE LABORATORIES LIMITED; WO2005/80367; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts