Month: December 2020

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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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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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 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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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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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: 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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Electric Literature 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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Some common heterocyclic compound, 69316-08-1, name is Methyl 4-(cyanoacetyl)benzoate, molecular formula is C11H9NO3, 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. Product Details of 69316-08-1

4-(5-Amino-2H-pyrazol-3-yl)-benzoic acid methyl ester The named compound is the 3-aminopyrazole used in the reaction of Example 23 and can be prepared from commercially available 4-(2-cyano-acetyl)-benzoic acid methyl ester by the following method: 4-(2-Cyano-acetyl)-benzoic acid methyl ester (1.0 gm.) is dissolved in 9.29 mL anydrous EtOH, treated with anhydrous hydrazine (0.37 mL) and heated to reflux. The resulting reaction mixture is refluxed for 24 h, subsequently cooled to room temperature, and concentrated in vacuo to provide the named compound in the amount of 0.45 gms.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 69316-08-1, its application will become more common.

Reference:
Patent; Allergan, Inc.; US6559173; (2003); B1;,
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Application of 2469-99-0,Some common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, molecular formula is C4H5NO, 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.

To a stirring suspension of quinolin-5-yl-hydra- zinc (0.25 g, 1.6 mmol) in 3:1 ethanol/deionized water (2.5 mE) was added 3-oxo-butyronitrile (0.13 g, 1.6 mmol). The reaction mixture was then heated at 60 C. for 2 h. After cooling to room temperature, the reaction mixture was concentrated in vacuo and the resulting crude product was used directly without further purification (0.21 g, 1.5 mmol, 94%)

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

Reference:
Patent; ChemoCentryx, Inc.; Cappel, Markus; (83 pag.)US2018/9797; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts