Month: March 2021

69395-13-7, name is 4-(2-Hydroxyethyl)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. HPLC of Formula: C9H9NO

Reference Example 2 2- [4-(4,5-Dihydro-lH-imidazol-2-yl)-phenyn -ethylamine dihvdrochloride a) 4-F2-C1 ,3-Dioxo-l ,3-dihydro-isoindol-2-ylVethyl1-benzonitrileUnder argon, a solution of 4-(2-hydroxy-ethyl)-benzonitrile [HeIv. CMm. Acta 64 (1981) 1688-1703] (4.49 g, 30.5 mmol), phthalimide (4.94 g, 33.55 mmol), triphenylphosphine (8.8 g, 33.55 mmol) and dimethyl formamide (100 mL) was stirred at 0 C for 20 minutes, then diethyl azodicarboxylate (7.59 mL, 48.8 mmol) was added dropwise at 0 0C. The so obtained reaction mixture was stirred at room temperature overnight, then poured into ice-water (740 mL). The precipitated product was filtered off, washed with water and dried. The crude product was recrystallized from 2-propanol to yield 7.83 g (93 %) of the title compound as a yellow solid.

The synthetic route of 69395-13-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RICHTER GEDEON VEGYESZETI GYAR RT.; WO2007/72092; (2007); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 591769-05-0, name is 3-Cyclopentylacrylonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 591769-05-0

To a solution of ethyl 4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d] pyrimidin-4-yl)-1H-pyrazol-3-formate (173 mg, 0.446 mmol, 1.0 eq.) and 3-cyclopentylacrylonitrile (135 mg, 1.11 mmol, 2.5 eq., prepared from the step A of Example 1) in acetonitrile (10 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (142 mg, 0.94 mmol, 2.1 eq.) at room temperature. The reaction liquid was stirred overnight at room temperature, then heated to 60¡ãC and reacted for 5 hrs. After the mixture was cooled to room temperature, the mixture was diluted with brine and ethyl acetate, and extracted with ethyl acetate. The combined organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The resulting residue was separated by column chromatography on silica gel column to give the titled compound (79 mg, 35percent yield), as a off-white solid. 1H NMR (CDCl3) delta 8.88 (1H, s), 7.98 (1H, s), 7.32 (1H, d, J = 3.6 Hz), 6.46 (1H, d, J = 3.6 Hz), 5.65 (2H, s), 4.27-4.35 (1H, m), 4.23 (2H, q, J = 7.2 Hz), 3.53 (2H, t, J = 8.4 Hz), 3.11 (1H, dd, J = 17.2 Hz, 7.6 Hz), 2.97 (1H, dd, J = 17.2 Hz, 4.0 Hz), 2.58-2.69 (1H, m), 1.88-1.99 (1H, m), 1.51-1.74 (4H, m), 1.22-1.30 (3H, m), 1.08 (3H, t, J = 7.2 Hz), 0.90 (2H, t, J = 8.4 Hz), -0.05 (9H, s). m/z=509[M+1]+.

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; Centaurus BioPharma Co., Ltd.; Chia Tai Tianqing Pharmaceutical Group Co.,Ltd; Lianyungang Runzhong Pharmaceutical Co., Ltd.; ZHU, Li; XIAO, Dengming; HU, Yuandong; DAI, Liguang; DUAN, Xiaowei; SUN, Yinghui; PENG, Yong; KONG, Fansheng; LUO, Hong; HAN, Yongxin; YANG, Ling; WANG, Shanchun; (94 pag.)EP3235819; (2017); A1;,
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Synthetic Route of 3441-01-8, 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. 3441-01-8, name is 3-Cyanobenzamide belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 27 A 70 wt. percent aqueous solution (100 ml) of sulfuric acid and m-cyanobenzamide (2.92 g) were placed in a 200-ml three-neck flask, and the resultant mixture was stirred. Subsequently, a 50 wt. percent solution (10 g) of nitrosylsulfuric acid, obtained through dissolution of nitrosylsulfuric acid (5 g) in sulfuric acid (5 g), was added dropwise to the mixture. When the addition was completed, the mixture was allowed to react at room temperature for 30 minutes. The precipitated crystals were collected, washed with water, and dried, to thereby obtain 2.68 g of m-cyanobenzoic acid (yield 92percent). The m-cyanobenzoic acid obtained had a purity of 98percent or more.

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-Cyanobenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Showa Denko Kabushiki Kaisha; US6433211; (2002); B1;,
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Electric Literature of 115279-57-7, 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. 115279-57-7 name is 2-(4-Aminophenyl)-2-methylpropanenitrile, 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.

Step D Synthesis Route B Amine V (crude product; 695 mg, 3.76 mmol) and nitrile IX (414 mg, 2.58 mmol) is suspended in dichloromethane (16 ml) under an N2 protective-gas atmosphere. 4-Methylmorpholine (0.6 ml, 5.46 mmol) is added. Bis(tri-chloromethyl) carbonate X (460 mg, 1.55 mmol) dissolved in dichloromethane (3 ml) is added dropwise over the course of about 15 min. at room temperature. The reaction solution is stirred at room temperature for a further 1.5 h. Water (30 ml) is added to the reaction mixture, which is then stirred vigorously for 10 min. The organic phase is separated, washed twice with water and dried using Na2SO4. The solvents are removed under reduced pressure in a rotary evaporator, giving 730 mg of crude product. The crude product is purified by means of column chromatography (80 g of Si60, CH2Cl2/5% MeOH), and the suitable fractions are combined. Removal of the solvents gives imidazolone XI (279 mg, 0.79 mmol, 51% yield) as yellow solid (see step E for the further processing of the crude mixture). Analytical data of imidazolone XI: TLC: Rf=0.31 (Si60, CH2Cl2/4% MeOH/1% NH3); m.p.: 167 C.; LC-MS: tR=2.056 min (UV=220 nm), tR=2.063 min. (TIC, with [MH]+=353); 1H NMR (400 MHz, DMSO) delta 8.40 (d, J=5.3, 1H), 7.63-7.55 (m, 2H), 7.51 (s, 1H), 7.39-7.29 (m, 3H), 7.15 (d, J=1.8, 1H), 3.35 (s, 3H), 1.74 (s, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Aminophenyl)-2-methylpropanenitrile, and friends who are interested can also refer to it.

Reference:
Patent; MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG; US2012/220587; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 2941-29-9, A common heterocyclic compound, 2941-29-9, name is Cyclopentanone-2-carbonitrile, molecular formula is C6H7NO, 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.

Intermediate 3d: benzyl N-[4-[(2-cyanocyclopenten-1 -yI)-(cyanomethyl)amino]-2- methoxy-phenyl]carbamate[00203] p-Toluenesulfonic acid monohydrate (1 .48g, 7.7gmmol) was added to a stirred solution of 2-oxocyclopentanecarbon itrile (9.35g, 85.71 mmol), benzyl N-[4-(cyanomethylamino)-2-methoxy- phenyl]carbamate (24.26g, 77.g2mmol) and toluene (600mL) at room temperature. The reactionwas then heated at reflux under Dean-Stark conditions for 4 hours. It was then cooled to room temperature and solvent removed until about lOOmL remained. Sat. aq. NaHCO3 (500mL) was then added and the resultant mixture was extracted with EtOAc (2 x 400mL). The combined organic extracts were washed with brine (500mL) and dried over Na2504. Solvent was removed in vacuo to give benzyl N-[4-[(2-cyanocyclopenten-1 -yl)-(cyanomethyl)amino]-2-methoxy-phenyl]carbamate(31 .36g, 77.92mmol, 100percent yield) as a brown solid which was used directly in the next step without further purification.MS Method 2: RT: 2.61, mlz 403.3 [M+H], 401.3 [M-H]

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; REDX PHARMA PLC; ARMER, Richard; BELFIELD, Andrew; BINGHAM, Matilda; JOHNSON, Alice; MARGATHE, Jean-Francois; AVERY, Craig; HUGHES, Shaun; MORRISON, Angus; (278 pag.)WO2016/51193; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, 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 1953-99-7, Application In Synthesis of 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile

To a 100 ml flask were added 3,4,5,6-tetrachlorophthalonitrile (5 g), 2,6-dibromophenol (2.45 g), K2CO3 (3.9 g) and N,N-dimethylformamide And the mixture was stirred while heating to 70 ¡ã C. After completion of the reaction, the reaction mixture is extracted with EA (ethyl acetate). After extraction and concentration, a solid can be obtained. The resulting solid is dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and vacuum dried to obtain 3,4,6-trichloro-5-(2,6-dibromo-phenoxy)-phthalonitrile.

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, 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Samsung SDI Co., Ltd; Seo Hye-won; Shin Myeong-yeop; Jeong Ui-su; Han Gyu-seok; (56 pag.)KR2019/11995; (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. 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8F4N2

With reference to Compounds 15 and 16, an exemplary synthesis and characterization of F34 cZn (hereinafter “Compound 15″) and F52Pc’Zn (hereinafter”Compound 16”) are depicted. In particular, twenty (20) thick walled glass reaction vessels(about 10 mL volume) are charged each with about 0.4 g (about 0.62 mmol) perfluoro-3,5,6- triisopropyl phthalonitrile, (depicted in FIG. 1 1 as P3 and hereinafter “Compound 14″), about0.04 g (about 0.2 mmol) tetrafluorophthalonitrile (depicted in FIG. 1 1 as P0 and hereinafter”Compound 13”) and about 0.04 g (about 0.22 mmol) zinc(II) acetate dihydrate. Then, catalytic amounts of ammonium molibdate, and about 1 mL nitrobenzene are added to each vial. The sealed vessels are heated in a microwave reactor at approximately 180 ¡ãC for about1 min. The crude solid of each vial is extracted with about 50 mL ethyl acetate, the organic fractions are combined, concentrated in vacuo and adsorbed to silica gel (mesh size approximately 70-230). Gel filtration using an acetone/hexane approximately 2:98 mixture(v/v) allows for the complete separation of nitrobenzene, unreacted Compound 14 and most yellowish impurities. The resulting blue-green solid is collected and subjected to column chromatography under gradually increasing solvent polarity. The rest of yellow impurities are removed with acetone/hexane approximately 2:98 mixture, followed by the separation of the green exemplary F52Pc’Zn, eluted with an approximately 10:90 mixture, the royal blue exemplary F34PcZn at approximately 20:80 polarity, and finally the dark blue exemplary Fi6PcZn as a side product using an approximately 40:60 mixture (v/v). The three colored fractions are evaporated and re-purified by gel filtration on short columns, eluting with the corresponding mixtures used for their initial separation. Removal of the solvent and drying of the compounds allows for isolation of exemplary FsaPc’Zn in about 13percent yield (about 0.42 g), exemplary T^PcZn in about 16percent yield (about 0.26 g) and exemplary FigPcZn in about 14percent yield (about 0.1 g), all based on starting material Compound 13.[0098] Specifically, the exemplary properties for Compound 15, i.e., F34PcZn, are as follows: Mp > 300 ¡ãC; UV-vis (CHC13): max (log e) 689 (5.09), 672 (4.99), 632 (4.44), 614 (4.41), 365 (4.69) nm (L mol 1 cm 1); IR (KBr): 1522, 1489, 1383, 1282, 1236, 1 133, 964 cm”1; 19F NMR (282 MHz, (CD3)2CO): delta -69.05 (6F, br, CF3), -72.25 (12F, s, CF3), -97.12 (IF, s, Ar-F), -131.4 (IF, s, CF), -135.09 (I F, d, Ar-F), -139.18 to -141.66.(5F, m, Ar-F), -149.92 to -151.6 (6F, m, Ar-F), -161.39 (IF, d, CF), -165.99 to -170.18 (I F, m, CF); HRMS (APCI+): calcd. for [M + H]+ (C4iHF34N8Zn)+ 1314.9067, found 1314.9080.[0099] With reference to FIG. 12, the measured exact mass spectrum (positive ion APCI) and isotope pattern of [M + H]+ for F34PcZn are depicted, indicating the calculated value for [M + H]+.[00100] Turning now to FIGS. 13(a)-(b), the UV-Vis electronic absorption spectra of F34PcZn are illustrated, showing solvent- dependent aggregation. In particular, FIG. 33(a) illustrates a spectrum recorded in chloroform, in which F34PcZn is a monomer, and FIG. 13(b) illustrates a spectrum recorded in ethanol, in which F34PcZn displays a significant degree of dimerization.[00101] Further, the exemplary properties for Compound 16, i.e., F52Pc’Zn, are as follows: Mp > 300 ¡ãC; UV-vis (CHC13): Xmm (log epsilon) 701 (5.10), 674 (4.97), 640 (4.62), 615 (4.44), 372 (4.78) nm (L mol”1 cm”1); IR (KBr): 1523, 1489, 1375, 1287, 1236, 1 166, 1 127, 1050, 966, 939, 737 cnT1 ; 19F NMR (282 MHz, (CD3)2CO): delta -63.23 (3F, br, C3/4 -68.52 (3F, br, CF3), -70.69 to -76.31 (30F, m, CF ), -97.56 (2F, br, Ar-F), -130.85 (I F, d, CF), -137.91 to -141 .55 (5F, m, Ar-F), -151.23 to -152.76 (4F, m, Ar-F), -161 .49 (I F, d, CF), -166.47 to -170.15 (3F, m, CF); HRMS (APCI+): calcd. for [M + H]+ 1764.8780, found 1764.8804.[00102] With reference to FIG. 14, the measured exact mass spectrum (positive ion APCI) and isotope pattern of [M + H].bul. for F52 c’Zn are depicted, indicating the calculated value for [00103] Turning now to FIG. 15, the X-ray structure of F52Pc’Zn(OPPh3) is depicted, showing a metal-coordinated triphenyl phosphine oxide molecule. The thermal ellipsoids are plotted at about 35percent probability and rotational disorder of the CF3 groups of -C3F7 is present, specifically shown as dashed lines.[00104] With reference to FIG. 16, the side view of the aggregation in solid state of F52Pc’Zn is illustrated. In particular, the toluene molecules in the crystalline lattice and the atoms of coordinated triphenyl phosphine oxide, except oxygen, have been omitted. Further, the /-C3F7 groups are shown in ball-and-stick representation and the interplanar stacking distance, approximately 3.663 A, proves the existence of pi-pi interactions.

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 1835-65-0.

Reference:
Patent; NEW JERSEY INSTITUTE OF TECHNOLOGY; GORUN, Sergiu, M.; LOAS, Andrei, Ioan; GRISWOLD, Kimberly; LAPOK, Lukasz; PATEL, Hemantbhai, Hasmukhbhai; GERDES, Robert; WO2012/61344; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, A new synthetic method of this compound is introduced below., Safety of 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile

Experiment 38; A range of experiments were conducted examining the resolution of diol with (+)-(S,S)-DTT. The general procedure is described below, and the details and results for each reaction are in table 1.Racemic diol (20 g, 58.4 mmol) was dissolved in approximately half of the solvent used for the experiment at 40 C. (+)-(S,S)-DTT.H2O (quantity specified in the table) was added as a solution in the other half of the solvent. The solution was held at 40 C. and was seeded within two minutes with crystals of (S)-diol.?(+)-(S,S)-DTT (approximately 5 mg). Crystallization typically began within 5-10 minutes after seeding. After 2 h at 40 C., the temperature of the solution was lowered to 20 C. over 2 h, and the solution was held at this temperature for a further 1 h. The product was then separated by filtration, washed with the appropriate solvent (2¡Á20 mL) and dried overnight at 60 C. under reduced pressure.

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; H. Lundbeck A/S; US2009/69582; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 115661-37-5, name is 2-Amino-3-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 115661-37-5, Recommanded Product: 2-Amino-3-fluorobenzonitrile

2-(1-cyclopropyl-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino)-3-fluorobenzonitrile2-Amino-3-fluorobenzonitrile (1.1 g, 8.08 mmol) and 1-cyclopropyl-4-methoxy-1H-pyrrol-2(5H)-one (1.170 g, 7.64 mmol) were combined in acetic acid (10 mL) and heated to 80 C. Methanesulfonic acid (1.311 mL, 20.20 mmol) was dissolved in acetic acid (2 mL) and added dropwise via syringe over 15 minutes. The reaction was stirred for 1 hour at 80 C. and then cooled to RT and placed on a rotoevaporator under high vacuum for 15 minutes at 55 C. to remove the acetic acid. The resulting oil was dissolved in methylene chloride (80 mL) and slowly added dropwise over 20 minutes to a solution of saturated aqueous sodium bicarbonate (70 mL) mixed with 5 N sodium hydroxide (20 mL). This resultant biphasic system was separated. The aqueous was extracted 2 more times with methylene chloride (60 ml) and all organics were combined, dried over magnesium sulfate, and filtered. The filtrate was evacuated to produce 1.5 grams of tan solid. This solid was dissolved in methylene chloride and methanol. Silica gel was added (10 g) and solvent removed. The residue was purified via flash column eluting with ethyl acetate/methylene chloride to afford 2-(1-cyclopropyl-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino)-3-fluorobenzonitrile as an off white solid (87%). 1H NMR (500.333 MHz, DMSO) delta 9.18 (s, 1H), 7.70 (m,1H), 7.45 (m, 1H), 4.49 (s, 1H), 3.99 (s, 2H), 2.57 (m, 1H), 0.65 (m, 4H). MS APCI, m/z=258 (M+H). HPLC 1.66 min.

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; ASTRAZENECA AB; US2008/318943; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

403-54-3, name is 3-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. Safety of 3-Fluorobenzonitrile

REFERENCE EXAMPLE 20 3-(4-Methyl-1-piperazinyl)benzonitrile According to a similar manner to that in Reference Example 17, the title compound was synthesised from 3-fluorobenzonitrile and 1-methylpiperazine. 1 H-NMR (CDCl3) delta (ppm): 2.35(3H, s), 2.55-2.60(4H, m), 3.21-3.25(4H, m), 7.06-7.13(3H, m), 7.28-7.31(1H, m).

The synthetic route of 403-54-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyowa Hakko Kogyo Co., Ltd.; US6127541; (2000); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts