Month: July 2021

Related Products of 243128-37-2, A common heterocyclic compound, 243128-37-2, name is 4-Fluoro-3-methoxybenzonitrile, molecular formula is C8H6FNO, 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 suspension of NaH (1.25 eq) in DMF (100 ml), to which is added 10 g of the product obtained during the preceding step, is stirred for 1 h at AT, then 4-fluoro-3-methoxy-benzonitrile (1 eq) in DMF (100 ml) is added and stirred a further 24 h at AT. After evaporation to dryness, the residue is redissolved in water, extracted with TBME, the organic layer is washed with a 1 N aqueous solution of NaOH then with an aqueous NaCl solution, dried over MgSO4, filtered and evaporated. 10.1 g of the desired product are isolated after chromatography on silica eluting with a DCM/MeOH/NH4OH mixture (97.5:2.5:0.1 v/v/v).

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; CEREP; US2009/233910; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

50712-68-0, name is 4-Chloro-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. name: 4-Chloro-2-methylbenzonitrile

General procedure: A solution of 1-acetyl-4-acetoxy-4-phenylazo-1,2,3,4-tetrahydroquinoline (8,0.25 mmol) in dry CH2Cl2 (2 mL) was added dropwise slowly to a mixture ofnitrile 9 (0.35 mmol) and AlCl3 (0.35 mmol) in CH2Cl2 (5 mL) at -40 C under an atmosphere of nitrogen (exothermic). After stirring at this temperature for0.5 h, the reaction was allowed to warm to room temperature and stirred foradditional 1 h. Then the mixture was cooled to 0 C and extracted with H2O(1 mL 3). The combined aqueous phase was concentrated under reducedpressure and purified by reverse flash column chromatography. The collectedfractions were lyophilized to afford the respective5,6-dihydro-4H-benzo[b][1,2,4]triazolo[1,5-d][1,4]diazepinium salt 10.For the chloride salt 10, reverse flash column chromatography conditions wereas follows: C18, acetonitrile = 5% in H2O and acetonitrile; 0.5% hydrochloricacid in H2O. For the trifluoroacetic salt 10, the reverse flash columnchromatography conditions were: C18, acetonitrile = 5% in H2O andacetonitrile; 0.5% trifluoroacetic acid in H2O.The picric salts 10 were obtained by exchanging the Cl- or CF3COO- anion bytreatment with picric acid. The following procedure was representative: 0.9-1.1%picric acid solution was added dropwise into the corresponding salt 10dissolved in H2O (1 mL) and a brown suspension appeared. The picric acidsolution was added dropwise continually until no further suspension appeared.The mixture was filtered, and the filtered cake was washed with H2O (0.5 mL 2), collected and dried in vacuum to give the picric salt 10.

The synthetic route of 50712-68-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Luan, Lin-bo; Song, Zi-jie; Li, Zhi-ming; Wang, Quan-rui; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 1826 – 1833;,
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Related Products of 6136-68-1, 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 6136-68-1 as follows.

3-Acetylbenzonitrile (5g, 34.4 mmol) is added to a flask containing (R)-(+)-2-Methyl-2- propanesulfmamide (3.48g, 28.7 mmol) and Titinium (IV) ethoxide (13.1 g, 57.4 mmol) in THF (70 mL) and the reaction mixture heated at 75C overnight. The reaction mixture is cooled (-48C) and L-Selectride (1M solution in THF, 57.4 mL) added dropwise over lhour. The reaction stirred for 2hrs and allowed to warm to room temperature. The reaction is then cooled to 0C and methanol (3 mL) added. Brine (150 mL) is added with stirring and the suspension filtered through celite. The crude material is extracted with ethyl acetate, dried (MgS04), filtered and evaporated under vacuum. The cruse is purified by column chromatography eluting with heptane-ethyl acetate to give N- |Y 1 S)- 1 -(3 -cyanophenyDethyl] – 2 -methyl- |”S(R)]- 2-propanesulfmamide (78 %)MS: 251 (M+H)lB NMR (300 MHz, CDC13): delta = 1.22 (s, 9H), 1.54 (d, 3H), 3.36 (bs, 1H), 4.55-4.7 (m, 1H), 7.43 (d, 1H), 7.46 (d, 1H), 7.56-7.6 (m, 2H), 7.64 (s, 1H).

According to the analysis of related databases, 6136-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; VANDEUSEN, Christopher L.; WEIBERTH, Franz J.; GILL, Harpal S.; LEE, George; HILLEGASS, Andrea; WO2011/44307; (2011); A1;,
Nitrile – Wikipedia,
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Application of 621-03-4, These common heterocyclic compound, 621-03-4, name is 2-Cyano-N-phenylacetamide, 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 mixture OF CYANOACETANILIDE (0.80 g, 5 mmol), 4-methoxy-3-buten-2-one (1 g, 10 mmol) and 1, 4-diazabicyclo [2,2, 2] octane (0.55 g, 5 mmol) in diethyleneglycol monomethylether was heated to 125 C for 5 h. The reaction mixture was partitioned between dichloromethane (100 ml) and 2M hydrochloric acid (100 ml). The organic layer was separated, washed with water, dried, filtered and evaporated. The residue was chromatographed on silica using heptane/ethyl acetate (1: 1) as eluent, affording the title compound (660 mg, 63%). ‘H NMR (CDCl3) : delta 7.78 (1H, d); 7.52 (3H, m); 7.17 (2H, dd); 6.22 (1H, d); 2.06 (3H, s)

Statistics shows that 2-Cyano-N-phenylacetamide is playing an increasingly important role. we look forward to future research findings about 621-03-4.

Reference:
Patent; ASTRAZENECA AB; WO2004/43924; (2004); A1;,
Nitrile – Wikipedia,
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Reference of 179898-34-1, A common heterocyclic compound, 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

To a solution of 2-(pyridin-2-yl)-4,5,6,7-tetrahydrooxazolo[5,4-c]pyridine (20 mg, 0.1 mmol) in toluene was added 3-bromo-5-fluorobenzonitrile (30 mg, 0.15 mmol), Cs2CO3 (65 mg, 0.2 mmol), Pd(OAc)2 (1 mg, cat.), and Xantphos (2 mg, cat.). The mixture was heated to 1000C and stirred overnight. The mixture was cooled, dissolved in MeOH, and filtered. The filtrate was concentrated and the residue was purified by preparative TLC to afford 3-fluoro-5-(2-(pyridin-2-yl)-6,7-dihydrooxazolo- [5,4-c]pyridin-5(4H)-yl)benzonitrile (10 mg, 31%) as a yellow solid. 1H NMR (400 MHz, CDCl3): delta 8.68 (d, IH); 8.05 (d, IH), 7.77 (t, IH), 7.32 (t, IH), 6.90 (s, IH), 6.75 (m, 2H), 4.40 (s, 2H), 3.68 (t, 2H), 2.80 (t, 2H); LC/MS: m/e = 321 (M+H)+.

The synthetic route of 179898-34-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SEPRACOR INC.; BURDI, Douglas; SPEAR, Kerry, L.; HARDY, Larry, Wendell; WO2010/114971; (2010); A1;,
Nitrile – Wikipedia,
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Some common heterocyclic compound, 1897-52-5, name is 2,6-Difluorobenzonitrile, molecular formula is C7H3F2N, 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. Computed Properties of C7H3F2N

Take a 500mL eggplant bottle,20.0 g of 2,6-difluorobenzonitrile was added,Anhydrous potassium carbonate 40.0 g and dimethyl sulfoxide 200 mL,Warming up to 90 C,Slowly drip morpholine 13.20g with stirring.TLC detects the progress of the reaction,After the reaction is completed, the reaction solution is naturally cooled to room temperature.Pour into the stirring ice water solution,18.0 g of white solid powder was precipitated.That is, 2-fluoro-6-morpholinylbenzonitrile (a).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1897-52-5, its application will become more common.

Reference:
Patent; Liaoning University; Liu Ju; Chen Ye; Gong Yilin; Wang Yang; Ding Shi; Shi Jiantao; Cao Shuwen; (12 pag.)CN108558763; (2018); 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. 501-00-8, name is 2-(3-Fluorophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 501-00-8

General procedure: General: To a solution of phenylacetonitrile 1 (1.0 eq) in methyl formate (10 eq), THF was added. In anhydrous condition, solution of NaH (1.25 eq) in THF was added dropwise to the reaction mixture at 0 C and the resulting mixture was stirred at room temperature overnight. After the reaction, the mixture was quenched with H2O, and several drops of 1 N HCl were added until the pH of the solution is lowered to 4 to 5. Then the mixture was extracted with methylene chloride and dried with MgSO4. After filtration and evaporation, the resulting solution was concentrated under vacuum to give the product 2 as yellowish oil in 72%-100% yields.

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 501-00-8.

Reference:
Article; Kim, Youngjae; Kim, Jeeyeon; Kim, Sora; Ki, Yooran; Seo, Seon Hee; Tae, Jinsung; Ko, Min Kyung; Jang, Hyun-Seo; Lim, Eun Jeong; Song, Chiman; Cho, Yoonjeong; Koh, Hae-Young; Chong, Youhoon; Choo, Il Han; Keum, Gyochang; Min, Sun-Joon; Choo, Hyunah; European Journal of Medicinal Chemistry; vol. 85; (2014); p. 629 – 637;,
Nitrile – Wikipedia,
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Application of 151-18-8, These common heterocyclic compound, 151-18-8, name is 3-Aminopropanenitrile, 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.

(4S)-4-{[(tert-butoxy)carbonyl]amino}-5-methoxy-5-oxopentanoic acid (700 mg, 2.52 mmol) was dissolved in DCM. 3-Aminopropanenitrile (228 mI, 3.03 mmol), DMAP (1.23 g, 10.1 mmol) and EDCI (581 mg, 3.03 mmol) was then added and stirred at rt for 18 h. The reaction mixture was diluted with DCM (50 ml.) and washed with 1 M HCI (50 ml.) and sat NaHCO3 (50 ml_). The organic phase was dried with Na2S04, filtered and concentrated to generate methyl (2S)-2-{[(tert- butoxy)carbonyl]amino}-4-[(2-cyanoethyl)carbamoyl]butanoate (762 mg, 91 %). LCMS [M+H]+ m/z 314; 1H NMR (400 MHz, CDCI3) d ppm 6.86 (br. s., 1H), 5.32 (d, J= 7.3 Hz, 1H), 4.23 – 4.38 (m, 1H), 3.76 (s, 3 H), 3.48 – 3.58 (m, 2 H), 2.65 (t, J= 6.5 Hz, 2 H), 2.29 – 2.36 (m, 2 H), 2.15 – 2.25 (m, 1H), 1.84 – 1.97 (m, 1H), 1.45 (s, 9 H).

The synthetic route of 151-18-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; BENGTSSON, Christoffer; BORHADE, Sanjay; HARALDSSON, Martin; HELLEDAY, Thomas; HENRIKSSON, Martin; HOMAN, Evert; PAULIN, Cynthia; SANDBERG, Lars; SCOBIE, Martin; STENMARK, Pal; VALLIN, Karl; (138 pag.)WO2019/201991; (2019); A1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1122-85-6, name is Phenyl Cyanate, 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 1122-85-6, Quality Control of Phenyl Cyanate

EXAMPLE 4 Preparation of 4-(p-Chlorophenyl)-4-methyl-2-pentynenitrile STR15 A solution of 1,1-dibromo-3-(p-chlorophenyl)-3-methyl-1-butene (38.5 g, 0.113 mol) in tetrahydrofuran is treated with n-butyllithium (0.25 mol, 100 mL of a 2.5M solution in hexane) under nitrogen over 45 minutes while maintaining the temperature below -65 C., stirred overnight at dry ice/acetone bath temperature, treated dropwise with a solution of phenyl cyanate (14.89 g, 0.125 mol) in tetrahydrofuran over 30 minutes at -65 C. to -70 C., allowed to warm to 10 C., and diluted with ethyl acetate and 5% sodium hydroxide solution. The resultant mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with 5% sodium hydroxide solution and water, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. The residue is distilled to give the title product as an oil (18.7 g, bp 110-113 C./0.9 mm Hg, 80.7% yield) Using essentially the same procedure, but substituting 1-(2,2-dibromovinyl)-1-(p-chlorophenyl)-cyclopropane for 1,1-dibromo-3-(p-chlorophenyl)-3-methyl-1-butene, 3-[1-(p-chlorophenyl)cyclopropyl]-2-propyne-1-carbonitrile is obtained as a yellow solid, mp 62-64 C.

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; American Cyanamid Company; US5849958; (1998); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 6621-59-6,Some common heterocyclic compound, 6621-59-6, name is 6-Bromohexanenitrile, molecular formula is C6H10BrN, 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 mixture of 2 (200mg, 0.34mmol), 6-bromohexanenitrile (180mg, 1.0mmol) and powdered NaH (95%; 17mg, 0.67mmol) in dry DMF (2.0mL) was stirred at room temperature under nitrogen for 2.5h. Saturated Na2CO3 buffer (6mL) was added, and the mixture extracted with ethyl acetate (25mL). The organic layer was washed with buffer (4×5mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using cyclohexane: ethyl acetate (1:1) containing 1% Et3N to give 133mg (57%) of 6 as a white foam: 1H NMR (CDCl3): delta 7.83 (d, J=7.2Hz, 2H, H-2?, H-6?), 7.38 (d, J=7.8Hz, 2H, H-3?, H-5?), 6.69 (d, J=8.1Hz, 1H, H-1), 6.54 (d, J=8.1Hz, 1H, H-2), 4.35 (s, 1H, H-5), 4.05-3.85 (m, 1H, H-1?), 3.80-3.57 (m, 1H, H-1?), 3.05 (d, J=6.3Hz, 1H, H-9), 3.03 (d, J=12Hz, 1H, H-10), 2.98-2.79 (m, 1H, H-8), 2.69 (dd, J=11.7Hz, J=4.8Hz, 1H, H-16), 2.52 (s, 3H, H-7?), 2.40 (t, J=7.2Hz, 2H, H-5?), 2.32-2.17 (m, 4H, H-10, H-16, H-22), 2.15-2.00 (m, 1H, H-15), 1.98-1.50 (m, 9H, H-7, H-15, H-18, H-2?, H-4?), 1.43 (s, 3H, H-21), 1.33-1.28 (m, 2H, H-3?), 1.23 (s, 3H, H-20), 1.18-1.00 (m, 2H, H-8, H-17), 0.93-0.79 (m, 1H, H-23), 0.78-0.62 (m, 1H, H-17), 0.61-0.46 (m, 2H, H-24, H-25), 0.2-0.07 (m, 2H, H-24, H-25); HRMS m/z calcd for [M+H]+ 661.3306, found 661.3328; Anal. Calcd for C38H48N2O6S: C, 69.06; H, 7.32; N, 4.24; found: C, 69.32; H, 7.20; N, 4.34.

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

Reference:
Article; Srivastava, Shefali; Fergason-Cantrell, Emily A.; Nahas, Roger I.; Lever, John R.; Tetrahedron; vol. 72; 40; (2016); p. 6127 – 6135;,
Nitrile – Wikipedia,
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