Category: nitriles-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 85363-04-8, name is N-(tert-Butoxycarbonyl)-2-aminoacetonitrile, 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 85363-04-8, Computed Properties of C7H12N2O2

N-Boc-aminoacetonitrile (40.2 g, 257.4 mmol) and N-acetylcysteine (42.0 g, 257.4 mmol) were dissolved in methanol (300 mL) at 60 C. and ammonia was passed through for 18 h. The solvent was removed in vacuo. After ion exchange chromatography (Amberlite IRA-400 (AcOH)) and recrystallisation from acetone, 28.4 g (53%) of the sub-title compound was obtained as a white solid. [0922] 1H NMR (300 MHz, CD3OD) delta4.41 (t, J=4.9 Hz, 1H), 4.01 (s, 2H), 2.91 (d, J=5.0 Hz, 2H), 2.01 (s, 3H), 1.46 (s, 9H)

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:
Patent; Inghardt, Tord; Johansson, Anders; Svensson, Arne; US2004/19033; (2004); A1;,
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Reference of 26391-06-0, 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. 26391-06-0, name is 2-Cyano-N,N-diethylacetamide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Typical procedure for the synthesis of alpha-cyano N-aryl ketene-N,S-acetals 1 (with 1a as an example). To a solution of ethyl cyanoacetate (10.0 mmol) in DMF (30 mL) at room temperature was added potassium carbonate (20.0 mmol) in one portion and the mixture was stirred for 1 h at room temperature. Phenyl isothiocyanate (10.0 mmol) was then added dropwise and the mixture was stirred for 2 h at room temperature. Then 1,2-dibromoethane (10 mmol) was added dropwise. The reaction was quenched with 200 mL of H2O after the mixture was further stirred for 6 h at room temperature. The resulting mixture was extracted with dichloromethane (3×30 mL), and the combined organic phase was washed with water, dried over anhydrous MgSO4, ltered, and evaporated in vacuo. The crude product was puried by silica gel chromatography (petroleum ether: diethyl ether=10:1) to give 1a (2.356 g) as a white solid.

The chemical industry reduces the impact on the environment during synthesis 2-Cyano-N,N-diethylacetamide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Wu, Chenwei; Huang, Peng; Sun, Zhongqiao; Lin, Mi; Jiang, Yuchun; Tong, Jian; Ge, Chunhua; Tetrahedron; vol. 72; 11; (2016); p. 1461 – 1466;,
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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. 646-20-8, name is Heptanedinitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 646-20-8

Example 1 5-(5-AMINO-1H-PYRAZOL-4-YL)-PENTANENITRILE (2) To a solution of 1,5-dicyanopentane (1) (6.5 mL, 50 mmol) and ethyl formate (20 mL, 250 mmol) in dry diethyl ether (200 mL), sodium hydride (60%, 4 g. 100 mmol) was added. The re-action mixture was refluxed for four h, cooled to room temperature filtered and rinsed with ether and dried. To a solution of above obtained white solid in 80% ethanol/water was added hydrazine hydrochloride (6.29 g. 61 mmol). The reaction mixture was adjusted to pH 3 with concentrated HCl and then refluxed for 2 h, cooled to room temperature and neutralized with NaHCO3. Solvent was removed under reduced pressure and the residue was dried in vacuum. The residue was suspended in ethanol and filtered. The filtrate was concentrated, dissolved in 5% MeOH/CH2C12, filtered through a short silica gel column, rinsed with 5% MeOH/CH2C12 and concentrated to give 5-(5-amino-1H-pyrazol-4-yl)-pentanenitrile 2 as a oil. LCMS(API-ES) m/z: 164.2, 165.1 [M+H+]; 163.1 [M-H+].

According to the analysis of related databases, 646-20-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chu, Shaosong; Nie, Zhe; Perretta, Carin L.; Erickson, Philip Eugene; US2008/70893; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 53312-80-4, name is 4-Amino-2-fluorobenzonitrile, 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 53312-80-4, Formula: C7H5FN2

Preparation 5; 4-Amino-2-fluorobenzoic acid; A mixture of 4-amino-2-fluorobenzonithle (25g, 0.183mmol) and potassium hydroxide (125g, 2.23mol) in water (35OmL) and industrial methylated spirit (5OmL) was heated at reflux for 48 hours. The solvent was evaporated in vacuo and the residue diluted with water (30OmL) and washed with DCM (20OmL). The aqueous phase was acidified to pH = 5.5 with concentrated HCI and the resultant precipitate collected by filtration to yield the title compound as a beige solid (23.94g, 0.154mol).

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:
Patent; PFIZER LIMITED; ICAGEN, INC.; MARKWORTH, Christopher John; MARRON, Brian Edward; SWAIN, Nigel Alan; WO2010/35166; (2010); A1;,
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Reference of 134450-56-9, The chemical industry reduces the impact on the environment during synthesis 134450-56-9, name is 4,5-Difluorophthalonitrile, I believe this compound will play a more active role in future production and life.

A solution of 5a (67 mg, 0.61 mmols) in DMF (10 mL) was treated NaH (60 %, 48mg, 1.2 mmols), allowed to stir for half a minute at room temperature followed by addition of phthalonitrile 6 (100 mg, 0.61 mmols). A deep blue coloration developed in the reaction flask and TLC monitoring in 10 minutes showed complete consumption of both starting materials 5a and 6 and appearance of a new spot more non-polar to both starting materials, which was very strongly UV-active. The reaction was quenched in cold water (100 mL), extracted into ethyl acetate (20 mL), organic layer repeatedly washed with brine solution (5 × 15 mL) and dried over sodium sulfate. Evaporation of the majority of ethyl acetate followed by re-crystallization in an ice-bath yielded 7a (single spot by TLC control, 30% Ethyl acetate/Petroleum ether) as buff-colored crystals. Yield (62 mg, 43%). 1H NMR (300 MHz, d6-DMSO): delta 7.82 (s, 2H), 7.05 (s, 4H); 13C NMR (150 MHz, d6-DMSO): delta 145.57, 140.06, 125.67, 121.99, 116.76, 115.27, 110.81; UV-vis (DMSO) lambdamax (log epsilon) 261 (4.53), 324 (3.48); HRMS (ESI+) calcd. for C14H6N2O2Na 257.0327, observed for C14H6N2O2Na 257.0293. Melting point: 311 C.

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, 4,5-Difluorophthalonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Banerjee, Subhadeep; Chattopadhyay, Anjan; Banerjee, Arnab; Haridas, Meera; Saini, Praveen; Das, Moitreyi; Majik, Mahesh S.; Maurya, Yogesh Kr.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 4; (2015); p. 753 – 757;,
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Related Products of 4640-66-8,Some common heterocyclic compound, 4640-66-8, name is 4-Chlorophenacylcyanide, molecular formula is C9H6ClNO, 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: General procedure: The substrate 1 (1.0 mmol) and thiourea 2(2.0 mmol) were added to solvent (5 mL methanol) at room tem-perature. To the reaction mixture, TBHP (3.0 mmol) and AIBN(0.2 mmol) were added respectively. The reaction mixture wasstirred at room temperature (for substrates 1a-f) or reux tem-perature (for substrates 1g-r) until TLC indicated the total consumption of 1 (for substrates 1p-q, the reaction time is 24 h).The residue was treated with saturated aqueous NaHCO3 (50 mL)and then extracted with EA (30 mL 3). The organic phase waswashed with brine (50 mL 1), dried over anhydrous Na2SO4. Thesolvent was removed and the residue was puried by ash columnchromatography on silica gel (EA/PE) to afford the desired compound 3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chlorophenacylcyanide, its application will become more common.

Reference:
Article; Sun, Jiyun; Ge, Huaibin; Zhen, Xiaohua; An, Xuechan; Zhang, Guangtao; Zhang-Negrerie, Daisy; Du, Yunfei; Zhao, Kang; Tetrahedron; vol. 74; 17; (2018); p. 2107 – 2114;,
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Electric Literature of 16932-49-3, 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. 16932-49-3 name is 2,6-Dimethoxybenzonitrile, 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.

General procedure: :2,6-dimethoxybenzonitrile (501 mg, 3.07 mmol) and4-amino-7-chloroquinoline (548 mg, 3.07 mmol) were dissolved together in 20 mLof anhydrous tetrahydrofuran. The vesselwas swept with nitrogen and chilled in an ice-water bath. Ethereal 3.0 M ethyl magnesium bromide (2.05 mL,6.14 mmol) was added dropwise over 3 min.After briefly forming an off-white solid suspended in a yellow solution,within minutes the mixture became a dark amber homogenous solution with someoff-white solid material remaining. Thevessel was placed in a 75 C oil bath for 21 h before diluting with 60 mL ofwater. The pH was decreased to ca. 14 byaddition of 4 pellets of NaOH. Themixture was then extracted with 60 mL of ethyl acetate, using solid NaCl tofacilitate partitioning. The organicswere dried over MgSO4 and concentrated to 1.27 g of a crude brownoily paste containing mostly unreacted starting materials. Flash chromatography (150 mL silica gel, 50%ethyl acetate / hexane, then neat ethyl acetate, then 10% methanol in ethylacetate) returned 100 mg (9.6%) ofN-(7-chloroquinolin-4-yl)-2,6-dimethoxybenzimidamide (G).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dimethoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Hershberger, Paul M.; Hedrick, Michael P.; Peddibhotla, Satyamaheshwar; Mangravita-Novo, Arianna; Gosalia, Palak; Li, Yujie; Gray, Wilson; Vicchiarelli, Michael; Smith, Layton H.; Chung, Thomas D.Y.; Thomas, James B.; Caron, Marc G.; Pinkerton, Anthony B.; Barak, Lawrence S.; Roth, Gregory P.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 262 – 267;,
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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 21524-39-0 as follows. HPLC of Formula: C7H3F2N

H) 3-fluoro-2-(4-methoxy-3-(4-(morpholin-4-yl)phenyl)-1H-pyrazolo[4,3-c]pyridin-1-yl)benzonitrile [1038] A solution of 4-methoxy-3-(4-(morpholin-4-yl)phenyl)-1H-pyrazolo[4,3-c]pyridine (355 mg), 2,3-difluorobenzonitrile (180 mg) and potassium carbonate in DMF (5 mL) was stirred at 100C for 2.5 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting solid was washed with petroleum ether to give the title compound (380 mg). MS(ESI+): [M+H]+ 430.2. MS(ESI+), found: 430.2.

According to the analysis of related databases, 21524-39-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; NARA, Hiroshi; DAINI, Masaki; KAIEDA, Akira; KAMEI, Taku; IMAEDA, Toshihiro; KIKUCHI, Fumiaki; EP2857400; (2015); A1;,
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These common heterocyclic compound, 77326-36-4, name is 2-Amino-6-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. Product Details of 77326-36-4

Example 24d 2-amino-6-(2-amino-2-methylpropoxy)benzonitrile To a solution of 2-amino-2-methylpropan-1-ol (14.4 g, 161 mmol) in anhydrous THF (150 mL) was added NaH (6.8 g, 161 mmol, 60% in mineral oil) in small portions at 0 C. under nitrogen. The mixture was stirred at 0 C. for 30 minutes and then stirred at room temperature for another 30 minutes. The solution was cooled down to 0 C. again, and to this solution was added dropwise a solution of 2-amino-6-fluorobenzonitrile (20.0 g, 147 mmol) in anhydrous THF (50 mL). The reaction mixture was then refluxed overnight under nitrogen. The reaction mixture was cooled down to room temperature and carefully quenched with aqueous NH4Cl solution and extracted with ethyl acetate (3*). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The crude mixture was purified by chromatography on silica gel eluting with 10% MeOH in DCM to give the title compound as yellow solid (23.4 g 71%). 1H NMR (400 MHz, DMSO-d6) delta 1.08 (s, 6H), 3.15 (s, 2H), 3.64 (s, 2H), 5.98 (s, 2H), 6.13 (d, J=8.0 Hz, 1H), 6.31 (d, J=8.4 Hz, 1H), 7.15 (t, J=8.4 Hz, 1H). MS 236 (MH+).

The synthetic route of 2-Amino-6-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SENOMYS, INC.; US2011/245353; (2011); 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. 149793-69-1, name is 3-Fluoro-5-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H3F4N

Synthesis of 3-(methylthio)-5-(trifluor e:[00376] In a 500-mL, 3 -neck round-bottomed flask equipped with an 100-mL pressure- equalizing addition funnel fitted with an nitrogen inlet, and a rubber septum, 3-fluoro-5- (trifluoromethyl)benzonitrile (8.0 g, 1.0 eq.), in acetone (40 mL). Sodiumthiomethoxide (3.42 g, 1.15 eq) was dissolved in water to make 21% aqueous solution and was added dropwise in 30 min at 5C temperature. The temperature of the reaction was slowly raised to RT and stirred for 3 h. Then temperature was raised to 50-60C and maintained for further 4-6 h. The progress of the reaction was followed by TLC analysis on silica gel with 10% MeOH – dichloromethane as mobile phase and visualization with UV, SM Rf =0.40 and Product Rf = 0.25. Reaction was stirred for 3 hr at 25C and 4-6 hrs at 50-60C and reaction mixture was transparent. The reaction mass was quench by water and extracted by ethyl acetate (3×100 mL). The combined organic layer was washed with brine 50 mL and dried over sodium sulphate and evaporated on buchi rotaevaporator. The resulting crude compound (8 g) was subjected to further stage Yield (80.9 %); Mass: (ES+) 235.94 (M+l).

The synthetic route of 149793-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KARYOPHARM THERAPEUTICS, INC.; SANDANAYAKA, Vincent, P.; SHACHAM, Sharon; SHECHTER, Sharon; MCCAULEY, Dilara; WO2012/99807; (2012); A1;,
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