Tag: M.W=100-200

Reference of 75279-55-9,Some common heterocyclic compound, 75279-55-9, name is 2-Chloro-6-fluorophenylacetonitrile, molecular formula is C8H5ClFN, 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 1–Preparation of alpha-[2-(4-chlorophenyl)ethyl]-2-chloro-6-fluorophenylacetonitrile A 3 neck 200 ml round bottom flask was charged with 7.5 gms of 60% NaH (0.187 mole, 1.5 eq.), washed three times with 25 ml hexanes, in 60 ml of 2:1 toluene:DMF. To this was added 21.2 gms (0.125 mole, 1.0 eq.) of 2-chloro-6-fluorophenylacetonitrile dropwise over 0.5 hour in 40 ml of 2:1 toluene:DMF. The reaction was stirred for 20 minutes at 10 C. then at room temperature for 1 hour after which 32.1 gms of 2-(4-chlorophenyl)ethyl methanesulfonate (0.137 mole, 1.1 eq.) in 60 ml of 2:1 toluene:DMF was added dropwise over 1 hour. Approximately 70 ml of 2:1 toluene:DMF was added to permit constant stirring and the reaction was stirred for an additional 3.5 hours after which gas liquid chromatography indicated the reaction was complete. Then 50 ml of water was added, followed by 10 ml of 10% HCl and 300 ml of ether. The ether was washed with 100 ml of water which was extracted twice with 50 ml of ether then washed with water. The combined ethers were dried and concentrated to give 40.0 gms of crude product which was distilled under reduced pressure. 26.6 gms (69.8%) of product resulted having a boiling point of 175-185 C. at 1 mm Hg. NMR (90 MHz): 2.2-2.9(m, 4H), 4.2-4.4(t, 1H) and 7.0-7.4(m, 7H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-6-fluorophenylacetonitrile, its application will become more common.

Reference:
Patent; Rohm and Haas Company; US5087635; (1992); A;,
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Application of 4553-07-5, 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. 4553-07-5, name is Ethyl 2-cyano-2-phenylacetate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To the suspension of ethyl phenylcyanoacetate (1.0 g, 5.3 mmol) in anhydrous ether (200 mL) was added lithium aluminum hydride at 0 C. The mixture was stirred at 0 C. for 18 h. After adding water (1 equiv.), 15% sodium hydroxide (1 equiv.) and water (3 equiv.) to the above solution, the precipitation was removed by filtration. The filtrate was concentrate to dry by lyophilization. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 0%-10% methanol in methylene chloride (0.1% NH4OH) in 30 min afforded 3-hydroxy-2-phenyl-propylamine (0.16 g, 20%).

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, Ethyl 2-cyano-2-phenylacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chen, Li; Chen, Shaoqing; US2006/4045; (2006); A1;,
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Related Products of 53312-81-5, 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. 53312-81-5 name is 5-Amino-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.

Ethyl 4-[ [(1 R)-2,2-difluoro- 1 -methyl-propyl] sulfamoyl] -3 -fluoro- 1 -methyl-pyrrole-2-carboxylate (150mg, 0.42 mmol) and 5-amino-2-fluorobenzonitrile (75.9 mg, 0.54 mmol) were dissolved in THF (5 mL). Lithium bis(trimethylsilyl)amide (1.67 mL, 1 M, 1.67 mmol) was added drop wise and the reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was quenched with sat. NH4C1 (aq;, 5 mL). The organic layer was removed and the aqueous layer extracted with CH2C12 (2 x 5 mL). The combined organic layers were evaporated to dryness andthe residue was purified by silica gel chromatography (ethyl acetate in heptane 0 to 100% and again with ethyl acetate in heptane 0 to 60%). The desired fractions were evaporated to dryness, the resulting residue was dissolved in refluxing isopropanol (7 mL) and sonicated to afford a suspension. The white solids were filtered and washed with isopropanol (1 mL) to afford compound 317 (115 mg) as off white powder. ?H NMR (400 MHz, DMSO-d6) oe ppm 1.07 (d,J6.8 Hz, 3 H), 1.58 (t, J19.1 Hz, 3 H), 3.45 – 3.61 (m, 1 H), 3.81 (s, 3 H), 7.48 – 7.54 (m, 1 H),7.54 (t, J9.2 Hz, 1 H), 7.96 (ddd, J9.2, 4.9, 2.6 Hz, 1 H), 8.04 – 8.37 (m, 1 H), 8.17 (dd, J=5.7, 2.6 Hz, 1 H), 10.32(br. s., 1 H). Method B: Rt: 0.98 minmlz: 431.1 (M-H)Exactmass: 432.1.

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

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
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Synthetic Route of 2032-34-0, A common heterocyclic compound, 2032-34-0, name is 3,3-Diethoxypropanenitrile, molecular formula is C7H13NO2, 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) (2E)-2-[bis(methyloxy)methyl]-3-[2-methyl-3-(trifluoromethyl)phenyl]-2-propenenitrile To a solution of 2-methyl-3-(trifluoromethyl)benzaldehyde (3.0 g, 16 mmol) and 3,3-bis(ethyloxy)propanenitrile (2.3 g, 20 mmol) in methanol (10 mL) was added a 25% sodium methoxide in methanol over 20 minutes. The mixture was stirred at room temperature overnight. Most of solvent was evaporated in vacuo and the residue was dissolved with ethyl acetate (30 mL) and water (15 mL). Two layers were separated. Organic layer was separated, washed with brine (15 mL), dried and solvent was evaporated in vacuo. The residue was then purified to give product. (3.66 g, 64%); 1H NMR (400 MHz, DMSO-d6) delta ppm 2.40 (s, 3H) 2.94 (m, J=11.37 Hz, 1H) 3.08 (m, J=4.80 Hz, 1H) 3.20 (s, 1H) 3.43 (d, J=10.36 Hz, 1H) 3.42 (d, J=11.12 Hz, 6H) 3.45-3.52 (m, 1H) 4.60 (d, J=4.80 Hz, 1H) 7.39 (t, J=7.71 Hz, 1H) 7.59 (dd, J=17.18, 7.83 Hz, 2H).

The synthetic route of 2032-34-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GlaxoSmithKline LLC; Lin, Hong; Luengo, Juan Ignacio; Moore, Michael Lee; Qu, Junya; Rivero, Ralph A.; Tedesco, Rosanna; Yu, Hongyi; US9096605; (2015); B2;,
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Application of 868-54-2,Some common heterocyclic compound, 868-54-2, name is 2-Aminoprop-1-ene-1,1,3-tricarbonitrile, molecular formula is C6H4N4, 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: Heterocyclic ketene aminals (1 mmol), aryl aldehydes (1.2 mmol), malononitriledimer (1.5 mmol), acetic acid (1 mmol), piperidine (1 mmol) and ethanol (10 mL)were stirred at refluxing for 1 h. After completion of the reaction (confirmed by TLC),the reaction mixture was filtered to afford the crude product, which was furtherwashed with 95% ethanol to give pure product 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-Aminoprop-1-ene-1,1,3-tricarbonitrile, its application will become more common.

Reference:
Article; Sun, Feilong; Zhu, Fengjuan; Shao, Xusheng; Li, Zhong; Synlett; vol. 26; 16; (2015); p. 2306 – 2312;,
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These common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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. Application In Synthesis of 4-Cyano-3-trifluoromethylaniline

a 4-[(4-Chloro-2-methyl-quinolin-7-ylmethyl)-amino]-2-trifluoromethyl-benzonitrile To a solution of 4-chloro-2-methyl-quinoline-7-carbaldehyde (example 13a, 180 mg, 0.875 mmol) in ethanol (3 mL) were added 4-amino-2-trifluoromethyl-benzonitrile (163 mg, 0.875 mmol), 25% aq. hydrochloric acid solution (1.5 mL), and sodium borohydride (207 mg, 5.25 mmol). The reaction mixture was stirred 16 h at r.t., then partitioned between ethyl acetate and 1 M aq. sodium hydroxide solution. The organic layer was washed with brine, dried (MgSO4), and evaporated. Flash chromatography (SiO2, hexane/ethyl acetate 1:1 afforded the title compound (123 mg, 37%). Off-white solid, ISP-MS: m/e=376.3 ([M+H]+).

The synthetic route of 4-Cyano-3-trifluoromethylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Klug, Michael G.; Mattei, Patrizio; Mueller, Werner; Neidhart, Werner; Nettekoven, Matthias Heinrich; Pflieger, Philippe; Plancher, Jean-Marc; US2003/158179; (2003); A1;,
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These common heterocyclic compound, 147754-12-9, name is 4-Fluoro-2-methylbenzonitrile, 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. Quality Control of 4-Fluoro-2-methylbenzonitrile

2-methyl-4-fluorophenyl-carbonitrile (2g, 14.8mM, 1.0equiv) in carbon tetrachloride (24mL) was added N- bromosuccinimide (2.64g, 14.8mM, 1.0equiv ), benzoyl peroxide (BPO, 179mg, 0.74mM, 0.05equiv), and heated to reflux for 3h under nitrogen. The reaction was complete by TLC, cooled to room temperature, filtered, washed with carbon tetrachloride, the solvent was concentrated under reduced pressure to give the crude product as a white solid. It was used directly in the next reaction without purification.

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

Reference:
Patent; Chengdu Bestchiralbio Limited-Liability Company; Li, Dequn; (16 pag.)CN105272963; (2016); A;,
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Reference of 64248-64-2, 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. 64248-64-2 name is 2,5-Difluorobenzonitrile, 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.

To a solution of (lR,3s,5S)-tert-butyl 3-((lr,4R)-4-hydroxycyclohexyloxy)-8- azabicyclo[3.2.1]octane-8-carboxylate (33 mg, 0.101 mmol) and 2,5-difluorobenzonitrile (18 mg, 0.129 mmol) in 0.5 mL THF, 1 M potassium teri-butoxide (0.150 mL, 0.150 mmol) was added slowly. After stirring at room temperature for 1 h, mixture was extracted with water and CH2C12. Organic phases were concentrated and residue was purified by HPLC (H20/CH3CN gradient + 0.1% TFA). Fractions containing product were partly concentrated and residue was extracted with 1 M NaOH and CH2C12. Organic phases were dried over MgS04, filtered, and concentrated to give (lR,3s,5S)-tert-butyl 3-((lr,4R)-4-(2-cyano-4-fluorophenoxy)cyclohexyloxy)-8- azabicyclo[3.2.1]octane-8-carboxylate (37.9 mg, 85.26 muiotaetaomicron?, 84.1%) as a white solid. Exact mass calculated for C25H33FN204: 444.2, found: LCMS m/z = 445.6 [M+H]+; lU NMR (400 MHz, CDC13) 5 ppm 1.41-1.69 (m, 8H), 1.47 (s, 9H), 1.87-2.10 (m, 8H), 3.50-3.56 (m, 1H), 3.77-3.85 (m, 1H), 4.16-4.31 (m, 2H), 4.33-4.39 (m, 1H), 6.92-7.00 (m, 1H), 7.20-7.26 (m, 2.4 Hz, 2H).

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

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; BUZARD, Daniel J.; HAN, Sangdon; KIM, Sun Hee; LEHMANN, Juerg; ZHU, Xiuwen; WO2013/55910; (2013); A1;,
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67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, 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 4-Fluoro-3-(trifluoromethyl)benzonitrile

A mixture of 4-fluoro-3-trifluoromethylbenzonitrile (75 mg, 0.40 mmol), sodium sulfinate (44.5 mg, 0.44 mmol) in N,N-dimethylformamide (1.5 mL) was heated at 100 C. for 2 h. The reaction mixture was cooled to room temperature, quenched with water. The resulting white solid was collected via filtration, washed with cold water, dried in a vacuum oven to give 4-methanesulfonyl-3-trifluoromethyl-benzonitrile (90 mg, 90% yield). This benzonitrile was hydrogenated in 2N NH3 in methanol with 35 mg of Raney Ni under a hydrogen balloon for 2 h. The reaction mixture was filtered through a celite plug, washed with methanol, evaporated in vacuo to give the titled compound.

The synthetic route of 67515-59-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liu, Gang; Sham, Hing L.; Szczepankiewicz, Bruce G.; Xin, Zhili; Zhao, Hongyu; Serby, Michael D.; Liu, Bo; Liu, Mei; US2006/173050; (2006); A1;,
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147754-12-9, name is 4-Fluoro-2-methylbenzonitrile, 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. Quality Control of 4-Fluoro-2-methylbenzonitrile

In a dried reaction flask, 4-fluoro-2-methylbenzonitrile (4.055g, 30.0mmol) and hydrazine hydrate (85percent) (3.54mL, 60.0mmol) were dissolved in ethanol (15.9mL). In the protection from light and under the nitrogen atmosphere, the solution was heated under reflux at 80¡ãC for 48hr. Water was added to the reaction solution. The mixture was filtered. The filtered cake was rinsed with water to produce a pale yellow solid, which was suspended in ethyl ether. A hydrogen chloride gas was passed into the suspension under an ice-salt bath. The suspension was filtered. The filtered cake was rinsed with ethyl ether to produce an off-white solid (2.04g) in 37.0percent yield.

The synthetic route of 147754-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KBP Biosciences Co., Ltd.; HUANG, Zhenhua; WANG, Jinyuan; ZHANG, Dedong; EP2607363; (2013); A1;,
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