Category: nitriles-buliding-blocks

These common heterocyclic compound, 1255870-63-3, name is 4-Bromo-2-ethoxybenzonitrile, 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. Product Details of 1255870-63-3

A suspension of 4-bromo-2-ethoxybenzonitrile (1.50 g, 6.5 mmol), hydroxylamine hydrochloride (913 mg, 13 mmol) and NaHCOs (1.365 g, 16.3 mmol) in water (1.32 mL) and EtOH (26.6 mL) is stirred in a sealed tube at 90 C for 3h. Once at RT, the product precipitated from the RM upon addition of water. The solid is filtered off under high vacuum, washing with water and some Et20. A first crop of pure title compound (947mg) was thus obtained as white solid. The filtrate is extracted with AcOEt. The organic layer is then washed twice with brine, dried over MgSO4, filtered and concentrated. The residue is purified by FC (hept AcOEt 5:5) to yield another crop of the pure title compound as a white solid (448 mg), merged with the first batch from precipitation. The title compound is obtained as a white solid (1.395 g, 83%). LC-MS A: tR = 0.53min, [M+H]+ = 259.03.

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

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; BOSS, Christoph; CORMINBOEUF, Olivier; FRETZ, Heinz; LYOTHIER, Isabelle; POZZI, Davide; RICHARD-BILDSTEIN, Sylvia; SIENDT, Herve; SIFFERLEN, Thierry; (160 pag.)WO2018/210992; (2018); A1;,
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Synthetic Route of 326-62-5, 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. 326-62-5, name is 2-(2-Fluorophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2- (2-fluorophenyl) acetonitrile (5.4 g, 40 mmol) in anhydrous THF (50 mL) was added dropwise of LDA (26 mL, 52 mmol, 1.3 eq) at -78. After addition, the mixture was stirred at -78 for 0.5 h. Then methyl benzoate (6.0 g, 44 mmol, 1.1 eq) in THF (10 mL) was added slowly and stirred at RT overnight. The suspension was quenched with NH4Cl solution (30 mL) and extracted with EA. The organic phase was washed with water and brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give 2- (2-fluorophenyl) -3-oxo-3-phenylpropanenitrile (12 g, crude) which was used directly to the next step without further purification. LC-MS: m/z 240.1 (M+H) +.

The chemical industry reduces the impact on the environment during synthesis 2-(2-Fluorophenyl)acetonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; TRAVINS, Jeremy, M.; KONTEATIS, Zenon, D.; SUI, Zhihua; YE, Zhixiong; (199 pag.)WO2018/39972; (2018); A1;,
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Synthetic Route of 14618-78-1, 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. 14618-78-1 name is 4,4-Dimethoxybutanenitrile, 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.

In a 500 ml four-necked flask,Add 100 grams of tetrahydrofuran,13.0 g (0.1 mol) of 4,4-dimethoxy-n-butyronitrile,13.0 g (0.1 mol) of 2,3-dichloropropenal,0.5 g DBU,Reaction at 60 C for 4 hours,The gas phase detection 1,4-addition reaction is completed.Cool down to 25-30 C,Add 15.0 grams of potassium carbonate,25.0 grams of 17% ammonia,8.0 grams of ammonium chloride,Reaction at 50 C for 5 hours,Cool down to 20-25 C,filter,20 grams of ice water wash filter cake,dry,Obtained 13.5 g of 5-chloro-7-azaindole,The liquid phase purity is 99.7%,The yield was 88.5%.

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

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Qi Yuxin; Zhang Mingfeng; Wang Sheng; Li Guangqian; Ju Lizhu; (7 pag.)CN110128421; (2019); A;,
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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.

(b) (2E)-3-Phenyl-2-propenimidamide; Cinnanionitrile (25.0 g, 194 mmol) was dissolved in EtOH. The solution was cooled to 0 0C and HCl gas bubbled through the solution for 30 minutes. The solution was stirred at ambient temperature for 1 h and then concentrated under vacuum. The residue was dissolved in EtOH (100 niL), cooled to 00C and a solution of NH3/Me0H (7M, 69 mL, 484 mmol) was added dropwise through an addition funnel. Once added, the solution was allowed to warm to ambient temperature and stirred overnight and the resulting NH4Cl was filtered off. The solution was concentrated under vacuum and the resulting product was used without further purification (28.6 g crude). LC-MS: m/z 147.4 (MH+).

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, (E)-Cinnamonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/3690; (2008); A1;,
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Electric Literature of 5414-21-1, These common heterocyclic compound, 5414-21-1, name is 5-Bromovaleronitrile, 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.

CH3Se3CH3 (100 mg, 0.53 mmol, Aldrich) was added to a solution of NaBH4 (60 mg, 1.59 mmol) in 5 ml of absolute EtOH under N2. After 5 min of vigorous reaction the colour of the solution changed from yellow to white. 5-Bromopentanenitrile (0.17 g, 1.06 mmol, Acros) was then added and stirred for 2.5 h. Et2O (10 ml) was added, the reaction mixture was washed with 5 ml each of water and brine, extracted with 2 x 25 ml of Et2O, and dried (MgSO4). The solvent was removed to give 10b as a yellow oil (107 mg, 57% yield). EI-ToF-MS (Fig. 2), m/z (rel. int.): 177 [M]+ (1200), 175 (28), 173 (15), 135 (10), 109 [CH3SeCH2]+ (33), 107 (17), 96 [CH3SeH]+ (27), 94 [CH2Se]+ (21), 93 [CHSe]+ (25), 82 (22), 55 (4). 1H NMR (500 MHz, CDCl3): delta1.75-1.88 (m, 4H, CH2CH2), 2.00 (s, 3H, CH3Se), 2.38 (t, 2H, J = 6.8 Hz, CH2CN), 2.57 (t, 2H, J = 6.9 Hz, CH2Se).

The synthetic route of 5414-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Matich, Adam J.; McKenzie, Marian J.; Lill, Ross E.; Brummell, David A.; McGhie, Tony K.; Chen, Ronan K.-Y.; Rowan, Daryl D.; Phytochemistry; vol. 75; (2012); p. 140 – 152;,
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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. 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 2-(3-Nitrophenyl)acetonitrile

To a solution of 3-nitro-phenyl-acetonitrile (3.20 g, 19.7 mmol) in MeOH(50 mL) was added Pd/C (10% wt, -50% H20, 0.32 g) and the mixture was placed under H2 (80 psi) and stirred for 2 days at 22 0C. The reaction mixture was filtered through Celite and the filtrate concentrated in vacuo to give crude product as a yellow oil. The residue was purified by silica gel chromatography (ISCO, elution with 0-10% ethyl acetate in hexanes) to give xix-1-1 (1.15 g, 44%): MS m/z = 133 (M-H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 621-50-1.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2006/41773; (2006); A2;,
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Related Products of 1835-65-0, 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. 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Thetetrafluoro Phthalo nitrile 6.0 g (30mmol), and the potassium fluoride 15 g(1.2eq.) and acetonitrile 20ml were put in the reactor in which the entrance of100ml placing the thermometer was 4 and it was stirred and it cooled to 0. Here, alpha – naphthol 4.3 g(1.0eq.) waslittle by little injected. In 5 orless the mixture after the input end, after it reacted at 1 hour thetemperature was increased to 20 and itreacted 2 hours at 20 through 25. Thereaction mixture was emitted to water after the completion of reaction and the segregatedsolid was filtered and it took out. The obtained crude product was well wipedoff with the methanol and the compound (4-3) 7.2g of the white solid wasobtained (the yield 74percent).

The chemical industry reduces the impact on the environment during synthesis 3,4,5,6-Tetrafluorophthalonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yamada Kagaku Kogyo Corporation; Yosuke, Manabe; Satoshi, Hayashi; (33 pag.)KR2015/107729; (2015); A;,
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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. 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate, A new synthetic method of this compound is introduced below., Quality Control of Ethyl 2-cyano-4,4-diethoxybutyrate

2-Methyl-4-hydroxypyrrolo[2,3-d]pyrimidine (3).; Acetamidine hydrochloride (2, 0.05 mol, 4.7 g) was added to the 0.1 M sodium ethoxide solution (75 ml) and kept stirring under room temperature for 0.5 h. After removing the formed sodium chloride by filtration, the filtrate was added the ethyl alpha-cyano-gamma,gamma-diethoxybutyrate (1, 0.05 mol, 11.5 g) and the solution was heated under reflux for 5 h. After the removal of most solvent under vacuum, acetic acid was added to adjust the pH to 7.0 and 10.8 g precipitation as white powder. Ethanol (110 ml) with concentrated sulfuric acid (2 ml) was added to the collected powder and was refluxed for 2 h. By the end of the reaction an equal volume of water was added and kept at 4° C. overnight. The pyrrolopyrimidine 3 precipitated as white powder (2.1 g) was used for next step without further purification.

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; Gangjee, Aleem; US2010/10016; (2010); A1;,
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Reference of 6011-14-9,Some common heterocyclic compound, 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, molecular formula is C2H5ClN2, 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: 2-Aminoacetonitrile hydrochloride 2 (7.0 mmol) and sodium acetate (8.0 mmol) were dissolved in 35 mL of methanol. Aldehyde 1 (7.0 mmol) was added to the grey solution, and the reaction mixture was stirred at room temperature. A solid suspension was formed after a few minutes (for compounds 3a, 3c, 3f and 3g). The suspension was stirred for 2 h and the solid filtered and washed with cold methanol, leading to the pure product 3. A second crop was isolated from the mother liquor after complete removal of methanol in the rotary evaporator, addition of dichloromethane (40 mL) and dry flash chromatography of the solution using dichloromethane (4×10 mL) as eluent. The solution was concentrated in the rotary evaporator and the yellow oil was kept at 0 C leading to the product 3 that was filtered and washed with cold diethyl ether. For compounds 3b, 3d, 3e and 3h-k, the reaction mixture was stirred at room temperature for 2 h. The solvent was removed in the rotary evaporator and dichloromethane (40 mL) was added to the mixture. Dry flash chromatography of this mixture was performed using 20 mL of dichloromethane as eluent. The solvent was removed in the rotary evaporator leading to a solid product. Cold diethyl ether was added to the suspension, kept for a few minutes in an ice bath. The solid was filtered and washed with cold diethyl ether, leading to the pure (arylideneamino)acetonitrile 3.

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

Reference:
Article; Costa, Marta; Proena, Fernanda; Tetrahedron; vol. 67; 10; (2011); p. 1799 – 1804;,
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Adding a certain compound to certain chemical reactions, such as: 935-02-4, name is 3-Phenylpropiolonitrile, 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 935-02-4, HPLC of Formula: C9H5N

General procedure: To a solution of cyanoacetylenes (0.4mmol) with N-tosylimines (0.2 mmol) in toluene (2 mL) was added Ph3P (0.2mmol). The mixture was then stirred at 110 C for 36 h in a reaction flask. Thenthe solvent was removed in vacuo and residue was purified by columnchromatography on silica gel to give the desired annulation product.

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

Reference:
Article; Zhang, Jinfeng; Zhang, Qi; Ji, Xin; Meng, Ling-Guo; Synlett; vol. 30; 9; (2019); p. 1095 – 1099;,
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