Tag: M.W=100-200

These common heterocyclic compound, 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, 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. Recommanded Product: 2-Chloro-4-fluorobenzonitrile

Cool a solution of diisopropylamine (80.6 niL, 0.575 mol) in THF (1 L) to about -5 0C using an ice water/MeOH bath. Add /z-butyllithium (2.5 M in hexanes, 212 mL, 0.530 mol) dropwise over 1 h via a syringe pump (4 mL/min) while maintaining the reaction temperature between -5 to 0 0C during the addition. Stir the lithium diisopropylamide (LDA) solution for 1 h at 0 C and then transfer it via canula, over 1 h, to a -78 0C solution of 2-chloro-4-fluoro-benzonitrile (68.7 g, 0.442 mol) in THF (1 L). Allow the temperature of the reaction mixture to warm to about -65 0C during the initial addition of the LDA solution; however, keep the internal temperature below -70 0C during the remainder of the LDA addition. Keep the temperature of the resulting dark red-orange reaction mixture below -70 0C for 5 h and add iodomethane (251.2 g, 1.77 mol, ~3 mL/min) at such a rate that the reaction temperature is maintained below -65 0C during the addition. Allow the reaction mixture to slowly warm overnight. After stirring for 14 h, the temperature of the reaction mixture is -5 0C. Quench the reaction with saturated aqueous ammonium chloride (500 mL) and water (750 mL) and dilute with diethyl ether (about 2 L). Separate the layers and extract the aqueous layer with diethyl ether (about 1 L). Dry the combined organic layer (about 5.5 L) over MgSO4, filter, and concentrate to afford the crude title compound as a red-brown oily solid (about 86.7 g). Subject the crude residue (dry loaded on silica gel using methylene chloride) to flash chromatography (silica gel (10 x 30 cm), gradient of 99: 1 to 93:7 hexane/EtOAc) to obtain the title compound (56.7 g, 76%) as a white solid, m.p. 63 – 65 0C; 1H NMR (300 MHz, CDCl3): delta 7.54 (dd, J= 8.6, 5.6 Hz, IH), 7.08 (dd, J = 8.6, 8.6 Hz , IH), 2.36 (d, / = 2.4 Hz, 3H).

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/124447; (2006); A2;,
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Synthetic Route of 628-20-6, 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. 628-20-6, name is 4-Chlorobutyronitrile, This compound has unique chemical properties. The synthetic route is as follows.

At 20 C, 31 g (0.5 mol) of ethylene glycol and 2.4 g (0.06 mol) of 60%(w%) sodium hydride. Then, the temperature was raised to 80 C, and 5.2 g (0.05 mol) of 4-chlorobutyronitrile was rapidly added dropwise. After the addition was completed, the reaction was continued for 30 min. After the reaction mixture was cooled to room temperature, the mixture was extracted twice with dichloromethane. The extract was dried over anhydrous sodium sulfate and evaporated to dryness to give 3.36 g of a pale yellow transparent liquid.Cyclopropionitrile was confirmed by NMR analysis. The yield was 97.2% and the purity was 97%.

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

Reference:
Patent; Xi’an Modern Chemical Institute; Li Bingbo; Ning Binke; Zhang Xiaoguang; Chen Tao; Wang Wei; Yang Cuifeng; Qian Yishi; (5 pag.)CN106242997; (2016); 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. 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. Computed Properties of C9H7N

In accordance with Scheme la, hydrogen chloride is bubbled through a solution ofcinnamonitrile 1 in methanol at room temperature. The volatiles are removed under reduced pressureand the resulting residue is triturated with ether and filtered to yield the intermediate imidate 2. Imidate2 is dissolved in methanol at ambient temperature, treated with amine 4 (commercially available fromAcros Chemicals) at ambient temperature and stirred under argon. The volatiles are removed underreduced pressure and the residue purified by preparative HPLC or trituration with ether to afford amidine3.

The synthetic route of 1885-38-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2004/108705; (2004); A1;,
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57381-51-8, name is 4-Chloro-2-fluorobenzonitrile, 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. HPLC of Formula: C7H3ClFN

a 4-Chloro-2-[(3-Hydroxy-1-Phenylpropyl)Amino]Benzonitrile A mixture of 3-amino-3-phenylpropanol (1 g, 6.6 mmol) and 4-chloro-2-fluorobenzonitrile (1 g, 6.4 mmol) in diisopropylethylamine (1.2 ml, 6.9 mmol) was heated at 140 C. for 5 h. The crude reaction mixture was cooled to room temperature and applied to a silica column. The title compound was isolated as a colourless solid (1.1 g, 58%) by elution with 20% diethyl ether/isohexane. MS APCI+vem/z287 ([M+H]+).

The synthetic route of 57381-51-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cheshire, David; Connolly, Stephen; Cox, David; Millichip, Ian; US2003/73685; (2003); A1;,
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Electric Literature of 1080-74-6, A common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, molecular formula is C12H6N2O, 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.

In the N2 environment, compound 3 (0.065 mmol) and 4 (0.390 mmol) were dissolved in 6 mL of chloroform solution.Three drops of pyridine solution were added dropwise, and the mixture was reacted at 75 C for 16 hours. The solvent was evaporated under reduced pressure and purified by residue column chromatography to yield white product NITI-1 (yield 86%).

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; Chinese Academy Of Sciences Chemical Institute; Zhu Xiaozhang; Xu Shengjie; Zhou Zichun; (23 pag.)CN109485635; (2019); A;,
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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. 403-54-3, name is 3-Fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H4FN

General procedure: CAUTION: Zn(ClO4)2.6H2O can cause skin and serious eye irritation and appropriate care should be taken in its use. In general, perchlorates are explosive compounds and appropriate caution should be taken including the avoidance of evaporation to dryness of perchlorate-containing residues. A mixture of the nitrile (1 mmol), halohydrocarbon (1.2 mmol) and Zn(ClO4)2¡¤6H2O (5 mol%) was placed in a round-bottom flask. Then the reaction mixture was heated at 80 C for the given time. After completion of the reaction (monitored by TLC), water (5mL) was added to the reaction mixture which was then extracted with ethyl acetate (3 ¡Á 5 mL). The organic layers were collected, combined, washed with water (3 ¡Á 10 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The pure product was obtained by passing the organic extract through a silica gel (200-300 mesh) column using petroleum ether (60-90 C)/ethyl acetate (10:1-5:1) as eluent and identified by 1H NMR and 13C NMR. The 1H NMR and 13C NMR spectra of the products are shown in the Electronic Supplementary Information.

According to the analysis of related databases, 403-54-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Feng, Chengliang; Yin, Guibo; Yan, Bin; Chen, Junqing; Ji, Min; Journal of Chemical Research; vol. 42; 7; (2018); p. 383 – 386;,
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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. 135748-35-5, name is 4-Chloro-2,5-difluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Chloro-2,5-difluorobenzonitrile

b [3-(5-Chloro-2-cyano-4-fluorophenoxy)-4-pentenyl]methylcarbamic Acid, 1,1-dimethylethyl Ester The subtitle compound was prepared according to the method of Example 3 step (b) using (3-hydroxy-4-pentenyl)methylcarbamic acid, 1,1-dimethylethyl ester and 4-chloro-2,5-difluorobenzonitrile in N,N-dimethylformamide. 1H NMR 300 MHz (CDCl3) 7.33 (1H, d), 7.00 (1H, d), 5.85 (1H, m), 5.30 (2H, m), 4.65 (1H, m), 3.35-3.51 (2H, m), 2.87 (3H, s), 1.97-2.10 (2H, m), 1.41 (9H, s).

According to the analysis of related databases, 135748-35-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cheshire, David; Connolly, Stephen; Cox, David; US2003/65174; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, 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 2338-75-2, category: nitriles-buliding-blocks

A solution of 5.0 g (27 mmol) of 4-(trifluoromethyl)phenylacetonitrile in 60 mL 2 M MeOH / NH3 was treated with 0.7 g of Raney Nickel. The mixture was then shaken on a Parr Apparatus under 50 psi of hydrogen for 18 h. The mixture was filtered through celite and the filtrate was concentrated in vacuo to afford 4.62 g of the product amine as brown oil. 1H NMR (CDC13, 400 MHz) 8:7.56-7.58, (d, 2H), 7.32- 7.34 (d, 2H), 3.00 (t, 2H), 2.8 (t, 2H).

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

Reference:
Patent; MERCK & CO., INC.; WO2005/110409; (2005); A2;,
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Adding a certain compound to certain chemical reactions, such as: 170572-49-3, name is 3-Fluoro-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 170572-49-3, Quality Control of 3-Fluoro-4-methylbenzonitrile

Example 11A 3-Fluoro-4-formylbenzonitrile The reaction was carried out under argon. 3-Fluoro-4-methylbenzonitrile (121 g, 895 mmol) and N,N-dimethylformamide dimethylacetal (245 g, 2.06 mol) were dissolved in DMF (1.8 liters) and stirred under reflux overnight. The content of the flask was then poured into water (2 liters), the mixture was extracted twice with ethyl acetate and the combined organic phases were washed with saturated sodium chloride solution. The organic phase was concentrated and the residue was redissolved in THF/water (1:1, 2.7 liters). Sodium periodate (503 g, 2.35 mol) was added, and the mixture was stirred at room temperature for one hour. The precipitate was then removed and the filtrate was recovered and extracted repeatedly with ethyl acetate. The combined organic phases were washed once with saturated sodium bicarbonate solution and once with saturated sodium chloride solution, dried and concentrated to give an oil. This oil was purified by column chromatography on silica gel (mobile phase: petroleum ether/dichloromethane 6:4, then 4:6, finally pure dichloromethane). The product fractions were concentrated. This gave 28.0 g (20% of theory) of the target compound as a white crystalline solid. GC-MS (Method 1): Rt=3.63 min; MS (ESIpos): m/z (%)=149.0 (48) [M]+, 150.0 (5) [M+H]+ 1H-NMR (400 MHz, DMSO-d6): delta=7.89 (d, 1H), 8.00 (t, 1H), 8.11 (d, 1H), 10.24 (s, 1H).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/94968; (2012); A1;,
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Application of 115661-37-5,Some common heterocyclic compound, 115661-37-5, name is 2-Amino-3-fluorobenzonitrile, molecular formula is C7H5FN2, 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) N-(2-cyano-6-fluorophenyl)-3-oxobutanamide (0714) To a mixture of 2-amino-3-fluorobenzonitrile (41.9 g), sodium acetate (30.3 g) and toluene (200 mL) was added diketene (28.2 mL) at 0C over 10 min. The reaction mixture was stirred at room temperature for 7 hr. To the reaction mixture were sequentially added toluene (150 mL) and diketene (4.7 mL) at room temperature, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was recrystallized from diisopropyl ether/ethanol to give the title compound (48.64 g). MS (ESI+): [M+H]+ 221.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-3-fluorobenzonitrile, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YOSHIDA, Masato; NAGAMIYA, Hiroyuki; OHBA, Yusuke; SETO, Masaki; YOGO, Takatoshi; SASAKI, Satoshi; TOKUNAGA, Norihito; ASO, Kazuyoshi; (298 pag.)EP2980089; (2016); A1;,
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