Month: July 2021

Adding a certain compound to certain chemical reactions, such as: 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, 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 4592-94-3, Computed Properties of C9H6BrNO

1.0 g (2.1 mmol) of N(4-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolane-2-yl)- 1 -tosyl- 1 H-pyffolo [2,3-b jpyridin-6-yl)cyclopropanecarboxamide prepared from the reaction formula 3 above was dissolved in DMF/H 20 = 2:1 solution, and then 0.6 g (2.5 mmol) of 3-(4-bromophenyl)-3-oxopropanenitrile, 0.2 g (0.2 mmol) of Pd(PPh ) and 0.15 mL of 2M K 2C0 aqueous solution were inserted thereinto and stuffed at 100 – 110C for 2 hours. Once the reaction was completed, the said mixture was cooled down at room temperature, then water was added thereto, and then an extraction using ethyl acetate was performed. After that, a solution extracted therefrom was dried by means of magnesium sulfate anhydrous and concentrated under reduced pressure, from which a residue was accordingly obtained. The residue was separated via NH-silica gel column chromatography (n-hexane / ethyl acetate = 5: 1), and N(4-(4-(2-cyanoacetyl)phenyl)- 1 -tosyl- 1 H-pyrrolo [2,3-b jpyridin-6-yl)cyclopropanecarboxamide was synthesized. A synthesized material was dissolved in MeOH/THF (1:1) solution, and then 2N sodium hydroxide aqueous solution was added thereto and stirred at 30 – 40C for 4 hours. Once the reaction was completed, the said mixture was cooled down to room temperature, and saturated ammonium chloride aqueous solution was added thereto while being stirred. A produced solid was filtered out, and finally a product, i.e., N(4-(4-(2-cyanoacetyl)phenyl)- 1 H-pyrrolo [2,3-b jpyridin-6-yl)cyclopropanecarboxamide was accordingly obtained.MS(ESI+) mlz 345 (M+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, 3-(4-Bromophenyl)-3-oxopropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CJ HEALTHCARE CORPORATION; LEE, Hyuk Woo; JI, Mi Kyung; KIM, Seung Chan; YU, Ha Na; JUNG, Soo Yeon; PARK, Ji-Yeon; LEE, Ye-Lim; LEE, Ho-Youl; KI, So Young; KIM, Dongkyu; KIM, Myeongjoong; (410 pag.)WO2019/78619; (2019); A1;,
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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. 622-75-3, name is 2,2′-(1,4-Phenylene)diacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H8N2

A mixture of 2,2′-(1,4-phenylene)diacetonitrile, 1-bromopyrrolidine- 2,5-dione (2.6 g, 14.73 mmol) benzoic peroxyanhydride (0.36 g, 1.47 mmol) in CCl4 (30 mL) was stirred at 75-80 C for 4 hours. A second reaction mixture of 2,2′-(1,4- phenylene)diacetonitrile (2.0 g, 12.81 mmol) 1-bromopyrrolidine-2,5-dione (2.279 g, 12.81 mmol) benzoic peroxyanhydride (0.310 g, 1.281 mmol) in CCl4 (30 mL) was stirred at 75- 80 C for 4 hours. The mixtures were combined, then concentrated. The residue was purified by flash chromatography (eluted by petroleum ether:ethyl acetate = 20:1 – 1:1) to afford 2-bromo-2-(4-(cyanomethyl)phenyl)acetonitrile (2.6 g, 11.1 mmol).1H NMR (400 MHz, CDCl3) delta ppm 7.32 (d, J = 8.2 Hz, 2H), 7.17 (d, J = 8.1 Hz, 2H), 5.23 (s, 1H), 3.51 (s, 2H).

According to the analysis of related databases, 622-75-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Nicholas David; BENOWITZ, Andrew B.; RUEDA BENEDE, Maria Lourdes; EVANS, Karen Anderson; FOSBENNER, David T.; KING, Bryan Wayne; LI, Mei; MILLER, William Henry; REIF, Alexander Joseph; ROMERIL, Stuart Paul; SCHMIDT, Stanley J.; WIGGALL, Kenneth; (1283 pag.)WO2017/216726; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, 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 1835-65-0, category: nitriles-buliding-blocks

EXAMPLE 45 Synthesis of Tetrafluoro-1,3-diiminobenz[f]isoindoline Anhydrous ammonia was slowly bubbled through a stirred mixture of tetrafluorophthalonitrile (2.0 g), 25percent sodium methoxide in methanol (2.3 ml), and dry 1-butanol (10 ml) for 20 minutes. With continued ammonia introduction, the mixture was refluxed for 1 hour. After the resultant had cooled, the solvent was removed under vacuum with a rotary evaporator. The residue was treated with ether (50 ml) and the product was collected by filtration, washed sequentially with water (10 ml), and ether (10 ml), vacuum dried and weighed (0.45 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,4,5,6-Tetrafluorophthalonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Buechler, Kenneth F.; Noar, Joseph B.; Tadesse, Lema; US2002/61602; (2002); A1;,
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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. 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C12H6N2O

Under nitrogen (N2) atmosphere20 mL of chloroform (CHCl3)Compound2 mL of pyridine was added to a solution of 9-1 (0.409 g, 0.20 mmol) and Compound E (0.39 g, 2.0 mmol).After the mixed solution was refluxed under a nitrogen atmosphere for 24 hours,Extracted with dichloromethane (CH2Cl2) and washed with water. After solvent removal, methyl chloride (MC) /Recrystallize through methanol, the product is hexane,Purification was carried out by chromatography using a silica gel column using ethyl acetate and chloroform (CHCl 3) as eluent.The resulting solid was recrystallized through chloroform.Then, washed with methanol and dried under vacuum432 mg of compound 9 was obtained. (Yield 90%)

The synthetic route of 1080-74-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; Im Bo-gyu; Jang Song-rim; Choi Du-hwan; Kim Ji-hun; (40 pag.)KR2019/117086; (2019); A;,
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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. 3672-47-7, name is 3-(4-Methoxyphenyl)-3-oxopropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 3-(4-Methoxyphenyl)-3-oxopropanenitrile

Intermediate 88A3-(4-Methoxyphenyl)-1 H-pyrazol-5-amineTo a solution of 3-(4-methoxyphenyl)-3-oxopropanenitrile (5.0 g, 28.5 mmol) in ethanol (100 mL) was added hydrazine hydrate (2.8 mL, 57.1 mmol) at room temperature. The mixture was heated to reflux for 8 h, allowed to cool and concentrated under reduced pressure to about ¼ volume (25 mL). The resulting precipitate was allowed to stir overnight at room temperature, filtered and rinsed with ethanol (2 mL). The title product was dried under vacuum. Yield 4.15 g (77%); LCMS m/z 190.1(M + H)+, . ret. time= 1.56 min.

The synthetic route of 3672-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITE DE MONTREAL; BOUVIER, Michel; MARINIER, Anne; RUEL, Rejean; RENE , Patricia; CHANTIGNY, Yves; DAGNEAU, Philippe; GINGRAS, Stephane; WO2012/100342; (2012); A1;,
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Electric Literature of 94088-46-7,Some common heterocyclic compound, 94088-46-7, name is 2-Fluoro-6-methoxybenzonitrile, molecular formula is C8H6FNO, 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: Example 1 Preparation of Compound Yhhu-0967 (5-methoxy-2,4-diaminoquinazoline) [0029] 2.53 g (79.08 mmol) of methanol was dropped into 5.18 g (86.27 mmol) of 40% sodium hydride suspension in tetrahydrofuran (150 ml) at 0 C. and stirred for 10 min, followed by dropwise addition of 10.0 g (71.89 mmol) of 2,6-difluorobenzonitrile in tetrahydrofuran (100 ml). The reaction mixture as stirred at room temperature for 10 h to complete the reaction. 200 ml of water was added thereto to destroy the excess sodium hydride, and the reaction mixture was extracted with 500 ml of ethyl acetate. The organic layer was dried with anhydrous sodium sulfate and evaporated to dryness. The residue was passed through column chromatography to provide an intermediate. The intermediate and 17.41 g (143.78 mmol) of guanidine carbonate were heated to 140 C. in 300 ml of N,N-dimethylacetamide and stirred for 8 h to complete the reaction. The reaction mixture was evaporated to dryness, then diluted with 200 ml of water and extracted with 400 ml of dichloromethane. The organic layer was dried with anhydrous sodium sulfate and then evaporated to dryness. The residue was passed through column chromatography to proved 9.85 g of compound Yhhu-0967 with a total yield of 72% in the two steps). [0030] 1H NMR (300 MHz, CHLOROFORM-d) d ppm 3.97 (s, 3H) 4.83 (br. s., 2H) 5.68 (br. s., 1H) 6.53 (d, J=8.06 Hz, 1H) 7.03 (d, J=8.55 Hz, 1H) 7.45 (t, J=8.18 Hz, 2H)

The synthetic route of 94088-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES; Zuo, Jianping; Hu, Youhong; Tang, Wei; Chao, Bo; Tong, Xiankun; Li, Dewen; Ji, Feihong; He, Peilan; US2013/261139; (2013); 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.

Under nitrogen protection100 g (523 mmol) of 4-trifluoromethylnicotinic acid and 600 mL of toluene were placed in a three-neck reaction flask with a reflux condenser and a constant pressure dropping funnel, and 125 g (1.05 mol) of SOCl2 was slowly added to the reaction flask at 0 C. It was refluxed at 120 C for 2.5 hours. The contents of the reaction flask were concentrated, and after cooling, 600 mL of THF was added. 100 g (1.08 mol) of aminoacetonitrile hydrochloride and 600 mL of toluene were placed in the previous reaction flask, and the reaction flask was cooled to 0 C to maintain the temperature, and 190 g (1.88 mol) of Et 3 N was slowly added. The reaction flask was reacted at 25 C for 10 hours, and then most of the THF solution was removed under reduced pressure, and water and ethyl acetate were added for extraction.After drying and concentrating the organic phase, 112 g (488 mmol) of the solid of flonicamid was obtained.The yield was 93.4%.

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:
Patent; Shanghai Heteng Fine Chemical Co., Ltd.; Chen Sheng; Shi Guancheng; Meng Haicheng; (10 pag.)CN108191749; (2018); A;,
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These common heterocyclic compound, 501-00-8, name is 2-(3-Fluorophenyl)acetonitrile, 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 501-00-8

A solution of 2-(3-fluorophenyl)acetonitrile (5.0 g, 37.0 mmol) and methyl iodide (5.06 mL, 81.4 mmol) in THF (100 mL) at 00C was added sodium bis(trimethylsilyl)amide, 1.0M solution in THF (81.4 mL, 81.4 mmol). After addition, the mixture was stirred at 00C for 45 minutes. Then, H2O (100 mL) and EtOAc (100 mL) were added and the mixture was stirred at room temperature for 15 minutes. The organic layer was collected and the aqueous was extracted with EtOAc (1 x 100 mL). The combined organic extracts were dried over MgSO4, concentrated, and dried in vacuo to give 2-(3-fluorophenyl)-2-methylpropanenitrile as orange oil which was used without purification.

The synthetic route of 2-(3-Fluorophenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2009/137404; (2009); A1;,
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Synthetic Route of 72115-09-4, The chemical industry reduces the impact on the environment during synthesis 72115-09-4, name is 5-Amino-2-bromobenzonitrile, I believe this compound will play a more active role in future production and life.

Step-1 : Synthesis of tert-butyl (4-bromo-3-cvanophenyl)carbamate. Di-tert-butyl dicarbonate (1.14g, 4.8mmol) was added to a solution of 5-amino-2- bromobenzonitrile (0.8g, 4mmol) and DMAP (0.58g, 4.8mmol) in DCM (20mL) and the resulting reaction mixture was stirred for 8h at room temperature. After completion of reaction, the reaction mixture was diluted with ice cold water and extracted with DCM (3×50 mL). The combined organic phase was washed with brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was purified by 100-200 mesh silica column by eluting with 15% ethyl acetate -hexane to afford the title compound (lg, 83%). LCMS: m/z = 297.15 (M+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, 5-Amino-2-bromobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; SAMAJDAR, Susanta; PODDUTOORI, Ramulu; MUKHERJEE, Subhendu; GOSWAMI, Rajeev; (174 pag.)WO2016/142855; (2016); A2;,
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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 1080-74-6 as follows. category: nitriles-buliding-blocks

To a degassed solution of intermediate 16 (75 mg, 0.06 mmol) and 3- (dicyanomethylidene)indan-l -one (87 mg, 0.45 mmol) in chloroform (1 .9 cm3) is added pyridine (0.36 cm3, 4.46 mmol) and the reaction mixture stirred at 23 C for 18 hours. Methanol (40 cm3) is added and the resulting suspension filtered and washed with methanol (3 x 10 cm3). The resulting solid is purified by column chromatography eluting with a graded solvent system (40-60 petrol:dichloromethane; 1 :1 to 2:3) to give compound 83 (63 mg, 65%) as a blue solid. 1H NMR (400 MHz CD2CI2) 8.75 (2H, s), 8.60 (2H, dd, J 7.1 , 1 1 .4), 7.84 (2H, dd, J 6.9, 1 .8), 7.63 – 7.80 (8H, m), 7.44 (2H, d, J 8.4), 7.39 (2H, d, J 4.2), 7.08 – 7.15 (8H, m), 7.04 (4H, d, J 7.6), 6.96 (4H, m), 2.49 (8H, t, J 7.6), 1 .49 (8H, t, J 4.2), 1 .09 – 1 .26 (24H, m), 0.68 – 0.76 (12H, m).

According to the analysis of related databases, 1080-74-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; MORSE, Graham; NANSON, Lana; MITCHELL, William; KROMPIEC, Michal; D’LAVARI, Mansoor; PRON, Agnieszka; (327 pag.)WO2018/65350; (2018); A1;,
Nitrile – Wikipedia,
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