Month: March 2021

Adding a certain compound to certain chemical reactions, such as: 868-54-2, name is 2-Aminoprop-1-ene-1,1,3-tricarbonitrile, 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 868-54-2, name: 2-Aminoprop-1-ene-1,1,3-tricarbonitrile

General procedure: In a 20 mL reaction vial, 4-hydroxycarbazole 1{1} (0.183g, 1mmol) with benzaldehyde 2{1} (0.106g, 1mmol), and 2-aminoprop-1-ene-1,1,3-tricarbonitrile 3 (0.132g, 1mmol) and ethanol (3 mL), as well as EtONa (0.064g, 1mmol)were mixed and then capped (the automatic mode stirring helped the mixing and uniform heating of the reactants). The mixture was heated for 15 min at 80 C under microwave irradiation. Upon completion, confirmed by TLC, the reaction mixture was cooled to room temperature. The crystalline solid product was collected by Buchner filtration, subsequently washed with two different solvents of ethanol and ethylether in sequence to give the pure product 4{1,1}.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Zhang, Wenhui; Wang, Jianqiang; Mao, Jingpeng; Hu, Li; Wu, Xiaohua; Guo, Cheng; Tetrahedron Letters; vol. 57; 18; (2016); p. 1985 – 1989;,
Nitrile – Wikipedia,
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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. 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H3ClFN

Preparation 12-Chloro-4-fluoro-3-methyl-benzonitrileTo a solution of diisopropylamine (474 mL, 3.35 mol) in anhydrous THF (5.8 L) at-5 C under a nitrogen atmosphere is added dropwise 2.5 M n-butyllithium in hexanes (1.24 L, 3.10 mol) over 3 h and the resulting mixture is stirred at -5 C for one additional hour. The LDA solution is added dropwise to a solution of 2-chloro-4-fluoro-benzonitrile (400 g, 2.58 mol) in anhydrous THF (5.8 L) at -70 C over 6 h and then stirred at -70 C overnight. lodomethane (643 mL, 10.32 mol) is added dropwise over 2.5 h and the temperature is raised to -5 C for 17 h. Saturated aqueous ammonium chloride (3 L) is added. The solution is diluted with water (3.5 L) and extracted with diethyl ether (2 x 2 L). The organic phases are separated, combined, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a black solid. The solid is purified through a silica gel pad eluting withEtOAc/hexanes (1/40) to obtain the title compound (323 g, 74%). 1H NMR (300 MHz, CDCls) delta 7.08 (dd, J= 8.6, 8.6 Hz, 1H), 7.54 (dd, J= 8.6, 5.6 Hz, 1H), 2.36 (d, J= 2.4 Hz, 3H).

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; ELI LILLY AND COMPANY; JADHAV, Prabhakar Kondaji; SAEED, Ashraf; GREEN, Jonathan Edward; KRISHNAN, Venkatesh; MATTHEWS, Donald Paul; STEPHENSON, Gregory Alan; WO2013/55577; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 236750-65-5, name is 4,5-Bis(2-methoxyethoxy)-2-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Formula: C13H16N2O6

(d) 2-amino-4, 5-bis (2-methoxyethoxy) benzonitrile:; To 4,5-bis (2-methoxyethoxy)-2-nitrobenzonitrile(10 g) was added acetic acid (75ml) and water(75ml), stirred the reaction mass for about 10 min, added Iron powder (7g) in portions over a period of 2hrs, Stirred the reaction mixture for about Vz hr at 300C adjusted PH of the reaction mass to 7. Extracted the material into ethylacetate, the organic layer was dried over sodium sulfate and concentrated to yield crystalline yellow solid. Which was further recrystallized from methanol (6g) mp 74-77 0C1HNMR (CDCI3): delta 3.43(s, 6H), 3.73(m, 4H), 4.08(m, 4H), 4.20(brs, 2H), 6.25(s, 1 H), 6.90(s, 1 H)

The synthetic route of 236750-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VITTAL MALLYA SCIENTIFIC RESEARCH FOUNDATION; WO2007/138612; (2007); A2;; ; Patent; VITTAL MALLYA SCIENTIFIC RESEARCH FOUNDATION; WO2007/138613; (2007); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 2973-50-4, name is 2-(2-Aminophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 2973-50-4

EXAMPLE 4 2,2,3,3,4,4,4-Heptafluoro-N-[2-(1H-tetrazol-5-ylmethyl)phenyl]butanamide A mixture of 2-aminobenzylcyanide (15 g) [Rousseau et al., JACS 72, 3047 (1950)], diisopropylethylamine (16 g) and dichloromethane (400 mL) was cooled in an ice bath under a nitrogen atmosphere. Heptafluorobutyryl chloride (28.9 g) in dichloromethane (100 mL) was added dropwise and the reaction was left to warm gradually to room temperature overnight. A 10% aqueous HCl solution was added and the organic phase was separated and dried over MgSO4. After filtration and concentration with a rotary evaporator, the crude, orange oil (42 g) was purified by high pressure liquid chromatography to give 35.4 g of 2,2,3,3,4,4,4-heptafluoro-N-[2-(cyanomethyl)phenyl]butanamide as a white solid, m.p. 76-79 C.

According to the analysis of related databases, 2973-50-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Home Products Corporation; US4764623; (1988); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 5922-60-1, 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 5922-60-1 as follows.

Example 4 – synthesis of 4-amino-6-chloro-quinazoline; A solution of 2-amino-5-chlorobenzonitrile (1.07 g, 7.0 mmol) in formamide (20 ml) was heated at 180 0C for 6 hours. After cooling to room temperature, water (30 ml) was added to the reaction mixture. The precipitate was collected by filtration, washed with water and dried over P2O5, yielding the title compound as a grey solid (1.2 g, yield: 95 percent) which was characterized by its mass spectrum as follows: MS (m/z): 180 ([M+H]+, 100).

According to the analysis of related databases, 5922-60-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; WO2008/9078; (2008); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 151-18-8, name is 3-Aminopropanenitrile, molecular formula is C3H6N2, 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. name: 3-Aminopropanenitrile

A process for preparing 2-methyl-4-amino-5-aminomethylpyrimidine, comprising the steps of:1), 30 parts of DMF and 50 parts of dimethyl sulfate was added to a four-necked flask, the temperature was raised to 75 C, the reaction was stirred for 4 h, and then cooled to -10 C;2), slowly add 50 parts of sodium methoxide methanol solution, drip, and stir for 10 minutes;3) slowly adding 28 parts of 3-aminopropionitrile, stirring for 40 min, and distilling under reduced pressure to obtain intermediate 1;4), further adding 140 parts of dichloromethane and stirring for 20min, filtering, and the filtrate is subjected to distillation under reduced pressure to obtain intermediate 2;5), 75 parts of sodium methoxide methanol solution was added to a four-necked flask, cooled to -4 C, slowly added 40 parts of acetonitrile hydrochloride, stirred for 30 min, filtered, the filtrate was transferred to another flask and intermediate 2 was added. And 40 parts of sodium hydroxide, liter After warming to 25 C and stirring for 16 h, a solution of 2-methyl-4-amino-5-aminomethylpyrimidine was obtained, and the yield was 92.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 151-18-8, its application will become more common.

Reference:
Patent; Nanjing Jinhao Pharmaceutical Technology Co., Ltd.; Wu Jianzhong; Liu Weiqiang; Tong Hebing; Jiang Lihua; Wang Bucheng; (4 pag.)CN109293580; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 453565-55-4,Some common heterocyclic compound, 453565-55-4, name is 5-Fluoroisophthalonitrile, molecular formula is C8H3FN2, 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: A mixture of aryl fluoride (51 a-d) (2.0 mmol), 5-chloro-2-methoxyphenol a (50 a) (0.32 g, 2.0 mmol) or 4-chloro-2-methoxyphenol (50 b) (0.32 g, 2.0 mmol) in DMSO (3.0 mL) and anhydrous K2C03 (0.41 g, 3.0 mmol) was heated at 120 C for 5 h. The mixture was poured into ice water and extracted with EtOAc (3 x 50 mL). The organic layer was sequentially washed with brine (2 x 75 mL), dried over anhydrous Na2S04, and concentrated in vacuo. The residue was purified by column chromatography to give 52 a-e and 36. 5-(5-chloro-2-methoxyphenoxy)isophthalonitrile (52 a): (0.28g, 50%) *H NMR (500 MHz, CDC13) 8 7.59 (d, J= 1.28 Hz, 1H), 7.32 (d, J= 1.32 Hz, 2H), 7.30 – 7.25 (m, 1H), 7.12 (d, J= 2.37 Hz, 1H), 6.99 (d, J= 8.84 Hz, 1H), 3.77 (s, 3H). 13C NMR (126 MHz, CDC13) delta 158.66, 150.14, 128.69, 127.30, 126.07, 123.27, 122.98, 118.60, 118.53, 116.32, 115.01, 113.97, 56.10.

The synthetic route of 453565-55-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YALE UNIVERSITY; WO2013/56003; (2013); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

1897-52-5, name is 2,6-Difluorobenzonitrile, 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. Computed Properties of C7H3F2N

Synthesis Route 21.5: 2-Fluoro-6-methoxybenzonitrile (analogous to WO 99/14187):640.5 g (4.6 mol) of difluorobenzonitrile were dissolved in 3.5 I of methanol and then cooled to 0-50C. 828.8 g of 30% strength sodium methoxide solution were added dropwise in this temperature range, and the reaction mixture was stirred at room temperature overnight. Then the reaction mixture was added to 20 I of water and the precipitate was filtered off with suction and washed twice with water and twice with heptane. The solid was dried in vacuo at 50C. Yield: 740 g (99% of theory) of a white solid with a purity of >95% according to GC.1H NMR (in CDCI3): delta = 3.95 ppm (s, 3H, 0-CH3), 6.85 ppm (m, 2H, arom. H), 7.5 ppm (q, 1H, arom. H). ;

The synthetic route of 1897-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF Aktiengesellschaft; WO2006/56433; (2006); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 621-50-1, name is 2-(3-Nitrophenyl)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 621-50-1, name: 2-(3-Nitrophenyl)acetonitrile

A mixture of nitrobenzene acetic acid (1 g, 5.52 mmoles), 1.66 mL OF SOC12, 10 mL dry CHC13 was refluxed for 14 hours. CHC13 and excess thionyl chlorid were removed in vacuo, and the residue was evaporated twice with 25 ML of toluene to remove traces of thionyl chlorid. The residue was taken into 10 mL of toluene and 30 ML of cold concentrated ammonium hydroxyde were added. The white solid formed was collected and dried with etanol in vacuo. Yield: 79 %. 1H NMR (DMSO-d6, 300MHZ) 8 : 8.14 (M, 2H), 7.71 (M, 2H), 7.06 (brs, 2H), 3.58 (s, 2H). 2- (3-NITROPHENYL) ACETAMIDE was added with 10 mL of POC13 and the mixture was heated at reflux for 2 hours. After cooling, the mixture was poured into ice, basified with NA2C03 and extracted with CH2C12. The organic layer was dried over NA2S04, filtered and evaporated. Purified by flash chromatography on silica gel CH2C12. Yield: 41% 1H NMR (CDC13, 300 MHz) 8 : 8.14 (M, 2H), 7.69 (d, 1H, J = 8HZ), 7.56 (m, 1H), 3.88 (s, 2H). A solution of 15 mL HBr 48% was cooled to 0C. (430 mg, 2.65 mmoles) of 3-nitrobenzonitrile, (574 mg, 4.85 mmoles) of Sn were added successively. The mixture was stirred at room temperature for 3 hours, then poured into ice. The solution was basified with NA2CO3, extracted with CH2CK, dried, filtered and evaporated. Purified by flash chromatography on silica gel ETOH/CH2CL2 (2: 98). Yield: 32% 1H NMR (DMSO-D6, 300MHZ) B : 7.37 (M, 2H), 6.81 (M, 2H), 3. 86 (s, 2H). 3-AMINOBENZONITRILE was then reacted with 2-chloroethylisocyanate as described in examples 1- 12 to obtain desired product. Purified by flash chrmatography on silica gel ETOH/CH2C12 (5: 95). Yield: 78%

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-Nitrophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IMOTEP INC.; WO2004/106291; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 179897-89-3,Some common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, molecular formula is C7H3BrFN, 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 7: 5-Brorno-N-l,3-thiazol-2-yl-lH-indazol-3-amne SCN[0275] Hydrazine monohydrate (2.6 mL, 52.5 mmol) was added to a solution of 5-bromo- 2-fluorobenzonitrile (3.50 g, 17.5 mmol) in ethanol (50 mL) at room temperature. The mixture was stirred for 4 h under reflux condition. After cooling, the mixture was diluted with EtOAc (300 mL), washed with H2O and brine, dried (MgSO4), filtered, and concentrated in vacuo. Purification by recrystallization (EtOAc-hexane) gave 3.37g (91%) of 5-bromo- lH-indazol-3-amine (compound 7A) as a white solid. 1H NMR (300 MHz, CDCl3) delta 4.07 (brs, 2 H) 7.20 (d, IH77=8.85 Hz) 7.42 (dd, IH, J=8.85, 1.70 Hz) 7.71 (d, IH, 7=1.51 Hz) 8.98 (brs, 1 H). MS (ES) [m+H] calc’d for C7H6BrN^, 213; found 211, 213. [0276] Ammonium thiocyanate (229 mg, 3 mmol) was added to a suspension of 5-bromo- lH-indazol-3-amine (212 mg, 1 mmol) in IN hydrochloric acid (3 mL). The mixture was stirred for 4 days at 1000C. The precipitate was collected, and washed with eta2O to give 231 mg (85%) of N-(5-bromo-lH-indazol-3-yI)thiourea (compound 7B) as a yellow solid. 1H NMR (300 MHz, DMSO-rf6) delta 7.43 (d, IH, 7=8.85 Hz) 7.50 (dd, IH, 7=8.85, 1.88 Hz) 8.49 (d, IH, 7=1.32 Hz) 8.79 (brs, IH) 9.18 (brs, IH) 10.85 (s, IH) 12.86 (s, IH). MS (ES) [m+H] calc’d for C8H7BrN4S, 272; found 270, 272.[0277] To a stirred solution of N-(5-bromo-lH-indazol-3-yl)thiourea (104 mg, 0.38 mmol) in ethanol (2 mL) and H2O (1 mL) was added 1 ,2-dichloroethyl ethyl ether (0.05 mL, 0.41 mmol) at room temperature. The mixture was stirred for 3 h at 8O0C. After dilution with EtOAc, the organic layer was washed with H2O and brine, dried (MgSO4), filtered, and concentrated in vacuo. Crystallization from EtOAc-diisopropyl ether gave 62.7 mg (55%) of 5-Bromo-N-l,3-thiazol-2-yl-lH-indazol-3-amine (compound 7) as a white solid. 1H NMR (300 MHz, DMSO-^6) delta 7.01 (d, IH, 7=3.58 Hz) 7.36 (d, IH, 7=3.58 Hz) 7.37 – 7.42 (m, IH) 7.44 – 7.49 (m, IH) 8.35 (d, IH, 7=1.32 Hz) 11.34 (brs, IH) 12.53 (s, IH). MS (ES) [m+H] calc’d for C10H7BrN4S, 296; found 294, 296.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-fluorobenzonitrile, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKEDA SAN DIEGO, INC.; WO2007/75847; (2007); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts