Tag: M.W=200-300

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. 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate, A new synthetic method of this compound is introduced below., HPLC of Formula: C11H19NO4

3,4-Dihydroxybenzamidine hydrochloride as obtained above (61.7 g) was dissolved in absolute ethanol (2000 ml.) and a part of the ethanol (1400 ml.) was subsequently distilled off again. More absolute ethanol (1400 mL) was added to this receiving solution, together with DBU (1 13 mL), 2-cyano-4,4-diethoxy-butyric acid ethyl ester (148.0 g) and triethyl amine (96 mL). The resulting mixture was heated until reflux and further refluxed for 57 hrs. Most of the solvent (1700 mL) was then distilled off while the remainder was allowed to cool to 50 0C. An aqueous solution of hydrochloric acid (2.3 M, 930 mL) was added slowly, then the reaction mixture was allowed to cool to ambient temperature and stirring was continued for 25 hrs. The resulting precipitate was filtered off, washed with water (3 x 150 mL) and dried in vacuo at 40 0C to yield 31.5 g 4-(4-hydroxy-7H-pyrrolo[2,3-d]pyrimidin-2-yl)- benzene-1 ,2-diol.

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; SOLVAY PHARMACEUTICALS GMBH; WO2009/153261; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 5866-98-8,Some common heterocyclic compound, 5866-98-8, name is 2,6-Dichloro-3-nitrobenzonitrile, molecular formula is C7H2Cl2N2O2, 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 3: Preparation of 4-chloro-7-nitro-1H-indazol-3 -amine To a stirred solution of 2,6-dichloro-3-nitrobenzonitrile (750.0 g, 3.45 mol, 1.0 equiv.) in ethanol (7.5 L, 10.0 V) at 15-20 C. was slowly added hydrazine hydrate (519.0 g, 10.36 mol, 3.0 equiv.) while maintaining the reaction mass below 25 C (Observation: Addition is slightly exothermic and solid formation will begin upon addition). The reaction mixture temperature was slowly raised to room temperature and then the mixture was stirred for 3 h (Observation: the quantity of solids will increase during this time). After completion of the reaction (monitored by TLC), the mixture was diluted with water (7.5 L, 10.0 V) and further stirred for 1 h at room temperature. The solids were isolated via filtration and then were washed with water (2.25 L, 3.0 V). The wet solid was washed with a 1 : 1 ratio mixture of acetone (1.875 L, 2.5 V) and hexanes (1.875 L, 2.5 V). Bulk residual water was removed from the solids by maintaining vacuum filtration for 60-90 min. The wet solid was finally dried in a hot air oven for 7-8 h at 50 C (until moisture content reaches below 1.5%) to get the dried product, 4-chloro-7-nitro-li/-indazol-3 -amine (549.0 g, 75% yield) as a brick red- colored solid. NMR (400 MHz, CDCb): d 10.36 (bs, 1H), 8.20 (d, J= 8.4 Hz, 1H), 7.07 (d, J= 8.40 Hz, 1H), 4.73 (bs, 2H).

The synthetic route of 5866-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BOWSHER, Michael S.; GILLIS, Eric P; PARCELLA, Kyle E.; (0 pag.)WO2020/89778; (2020); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 13338-63-1, name is 3,4,5-Trimethoxyphenylacetonitrile, 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 13338-63-1, Quality Control of 3,4,5-Trimethoxyphenylacetonitrile

Using the method of synthesizing an intermediate similar to that of Example 1, Take 0.193 g (0.01 mol) of 2-(3,4,5-trimethoxyphenyl)acetonitrile (5), 0.156 g (0.01 mol) of 2-naphthaldehyde, and 20 mL of methanol into a 50 mL three-necked flask. Stirring to 60 C, adding sodium methoxide 0.027 g (0.005 mol), Constant temperature reaction for about 5h, thin layer chromatography to follow the reaction, After the reaction is completed, cool to room temperature, filter, and wash. Dry and recrystallize from methanol to give a pale yellow solid. Yield: 40.6%,

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, 3,4,5-Trimethoxyphenylacetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Yanbian University; Tian Yushun; Li Jiajun; Ma Jun; (19 pag.)CN109384689; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 79463-77-7, name is Diphenyl N-cyanocarbonimidate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 79463-77-7

A mixture of 3,4,5-trimethoxyaniline (1.83 g, 10 mmol) and diphenyl-cyanocarbon-imidate (2.62 g, 11 mmol) in iso-propanol (30 mL) was stirred at 100-1l0oC for 1h. The reaction was cooled and filtered, washing with ether to provide the title compound (2.79 g, 85% yield) as a white solid. 1H-NMR (500 MHz, DMSO-d6) 10.8 (s, 1H), 7.45 (t, 2H), 7.31 (m, 3H), 6.83 (s, 2H), 3.76 (s, 6H), 3.65 (s, 3H) ppm; MS (FIA) 328.1 (M+H); HPLC (method A) 3.211 min.

The synthetic route of 79463-77-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2004/46120; (2004); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 330793-38-9, These common heterocyclic compound, 330793-38-9, name is 4-Bromo-2-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.

A mixture of 4-bromo-2-methoxybenzonitrile (3.0 g, 14 mmol) , Boc2O (3.24 g, 15.6 mmol) , and Raney Ni (10, 0.6 g) in EtOAc (100 mL) was heated under 40 psi H2atmosphere at 70 for 36 h. The product mixture was filtered, and the filtrate concentrated. The residue was purified by silica gel chromatography eluting with EA: PE 1:30 to 1:10 to afford the title compound.1H NMR (400 MHz, CDCl3) delta 7.09-7.18 (m, 1H) , 7.01 -7.08 (m, 1H) , 6.98 (s, 1H) , 4.23 (d, J 5.8 Hz, 2H) , 3.83 (s, 3H) , 1.44 (s, 9H) . MS : m/z 259 (M – 56) .

The synthetic route of 330793-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COOKE, Andrew J.; PITTS, Daniel; JOHNSON, Adam; BESHORE, Douglas C.; HURZY, Danielle; MITCHELL, Helen; FRALEY, Mark; MCCOMAS, Casey; SCHIRRIPA, Kathy; MERCER, Swati P.; NANDA, Kausik; MENG, Dongfang; WU, Jane; BABAOGLU, Kerim; LI, Chun Sing; MAO, Qinghua; QI, Zhiqi; (156 pag.)WO2016/54807; (2016); A1;,
Nitrile – Wikipedia,
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Synthetic Route of 138642-47-4, These common heterocyclic compound, 138642-47-4, name is 2-Bromo-5-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.

General procedure: To a mixture of substituted alcohol 1 (1 mmol) and substituted nitrile 2 (1 mmol), T3P 50 wt% in ethyl acetate (50 mol%) was added and stirred at 90 C. After the reactant disappeared (monitored by TLC), the reaction mixture was cooled to room temperature, excess of water was added and extracted with ethyl acetate and combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by recrystallization using DCM: pet ether (1:9) mixture to get pure compound 3.

The synthetic route of 138642-47-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chaithra, Nagaraju; Mantelingu, Kempegowda; Rangappa, Kanchugarakoppal S.; Rangappa, Shobith; Sandhya, Nagarakere C.; Swarup, Hassan A.; Synthetic Communications; vol. 49; 16; (2019); p. 2106 – 2116;,
Nitrile – Wikipedia,
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328-87-0, name is 2-Chloro-5-trifluoromethylbenzonitrile, 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. Safety of 2-Chloro-5-trifluoromethylbenzonitrile

EXAMPLE 7 Preparation of 2-Cyano-alpha,alpha,alpha-trifluoro-p-tolyl-3-ethoxy-4-nitrophenyl ether A solution of potassium hydroxide (2.6 g., 0.04 mole) 87.3% pure and 3-ethoxy-4-nitrophenol (7.3 g., 0.04 mole) in methanol (30 ml) is stripped to dryness under reduce pressure. A residue of potassium 3-ethoxy-4-nitrophenoxide is dissolved in sulfolane (200 g.) and 4-chloro-3-cyano-benzotrifluoride (8.2 g., 0.04 mole) is added. Gas-liquid chromotography shows the reaction to be complete after stirring at 110 C. for 41/2 hours and 135 C for 21/2 hours. The reaction mixture is cooled and poured into deionized water and the precipitate which forms is filtered off and air dried. Recrystallization from isopropanol yields 2-cyano-alpha,alpha,alpha-trifluoro-p-tolyl-3-ethoxy-4-nitrophenyl ether (7.4 g. 53%) m.p. 143-145 C.

The synthetic route of 328-87-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rohm and Haas Company; US4063929; (1977); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 179897-89-3, 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. 179897-89-3 name is 5-Bromo-2-fluorobenzonitrile, 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.

At room temperature,to2-Fluoro-5-bromobenzonitrile (5.0 g)Soluble in ethanol (30mL)80% hydrated hydrazine (7.82g) was added to the solution.After refluxing at 90 C. for 12 h, the reaction solution was cooled to room temperature.Concentrate under reduced pressure to remove the ethanol.The residue was slurried with dichloromethane for 1 h.Filter, wash with dichloromethane, dry,The title compound (5.3 g) was obtained.

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

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Beijing Sai Lintai Pharmaceutical Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; Zhu Li; Hu Yuandong; Dai Liguang; Yang Yanqing; Duan Xiaowei; Yang Zhao; Wu Wei; Sun Yinghui; Han Yongxin; Peng Yong; Luo Huiyan; Luo Hong; Yang Ling; Xu Hongjiang; Guo Meng; Zhong Zhaobo; Wang Shanchun; (102 pag.)CN108003161; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 138642-47-4, These common heterocyclic compound, 138642-47-4, name is 2-Bromo-5-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.

General procedure: To a mixture of substituted alcohol 1 (1 mmol) and substituted nitrile 2 (1 mmol), T3P 50 wt% in ethyl acetate (50 mol%) was added and stirred at 90 C. After the reactant disappeared (monitored by TLC), the reaction mixture was cooled to room temperature, excess of water was added and extracted with ethyl acetate and combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by recrystallization using DCM: pet ether (1:9) mixture to get pure compound 3.

The synthetic route of 138642-47-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chaithra, Nagaraju; Mantelingu, Kempegowda; Rangappa, Kanchugarakoppal S.; Rangappa, Shobith; Sandhya, Nagarakere C.; Swarup, Hassan A.; Synthetic Communications; vol. 49; 16; (2019); p. 2106 – 2116;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 36282-26-5, 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 36282-26-5 as follows.

A mixture of 4-fluoro-2-bromobenzonitrile (10.0 g, 50.0 mmol), potassium acetate (9.82 g, 100 MMOL), bis (pinacolato) diboron (14.0 g, 55.0 mmol) and dichloro [L, L’-BIS (diphenylphosphino) FERROCENE] PALLADIUM (II) CH2CL2 adduct (0.82 g, 1.0 mmol) in 1,4-dioxane (150 ml) and dimethylsulfoxide (3 ml) was degassed with nitrogen for 1 h then heated at 85C for 20 h. The reaction was cooled to ambient temperature and then concentrated in vacuo. The residue was stirred with 2 N sodium hydroxide (250 ml) for 10 min then filtered. The filtrate was extracted with diethyl ether (300 ml) and the organics discarded. The aqueous component was cooled to 0C then treated with 5 N hydrochloric acid, added dropwise over 15 min until the pH was 8. The aqueous phase was extracted with EtOAc (2 x 200 ML), THE COMBINED organics were dried over anhydrous sodium sulfate, filtered and evaporated to afford the title compound (10.9 g, 88%) as a pale brown solid: BA (360 MHz, CDCL3) 1.38 (12 H, s), 7.15-7. 25 (1 H, M), 7.53-7. 60 (1 H, m), 7.67-7. 75 (1 H, m).

According to the analysis of related databases, 36282-26-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/65388; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts