Category: nitriles-buliding-blocks

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. 3939-09-1, name is 2,4-Difluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2,4-Difluorobenzonitrile

2-(Benzyloxy)-4-fluorobenzonitrile. Benzyl alcohol (13 mL, 125 mmol) was slowly added to a stirred suspension of NaH (95%, 2.86 g, 113 mmol) in toluene (200 mL) at room temperature. After 30 min, 2,4-difluorobenzonitrile (15.3 g, 110 mmol; Aldrich) was added all at once and stirring continued overnight (18 h). After this, the reaction mixture was washed with water (2 X 25 mL) and brine (25 ml). The organic layer was dried (Na2SO4), filtered and concentrated to give a white slurry which was triturated with hexanes and filtered to afford the title compound as a white solid (20.34 g, 81% yield). 1H NMR (500 MHz, CDCl3): 7.59-7.55 (IH, m), 7.45-7.34 (5H, m), 6.75-6.71 (2H, m), 5.19 (2H5 s); 13C NMR (125.76 MHz, DMSO-d6) delta ppm: 71.16, 98.75, 101.54, 101.75, 108.66, 108.84, 115.83, 127.16, 12.8.58, 128.94, 135.03, 135.44, 135.54, 162.22, 162.31, 165.26, 167.29. LCMS calcd for C14H11FNO: 228.2; found: 228.0.

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 3939-09-1.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/64316; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 19924-43-7, name is 2-(3-Methoxyphenyl)acetonitrile, 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 19924-43-7, Safety of 2-(3-Methoxyphenyl)acetonitrile

A mixture of (3-methoxyphenyl)acetonitrile (13.0 g, 88.0 mmol), O,O-diethyl dithiophosphate (14.9 mL, 97.0 mmol) and 4M hydrogen chloride-1,4-dioxane (177 mL, 707 mmol) was stirred at room temperature for 18 hr. The reaction mixture was diluted with ethyl acetate (200 mL), water (200 mL) was added, and the organic layer was separated, washed successively with water (100 mL), 0.2N aqueous sodium hydroxide solution (100 mL) and saturated brine (100 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was treated with hexane (200 mL) in an ice bath to allow solidification. The solid was collected by filtration, and washed with hexane to give the title compound (12.6 g) as a white solid (yield 79%). 1H NMR (400 MHz, CDCl3) 5 3.81 (3H, s), 4.10 (2H, s), 6.49 (1H, brs), 6.80-6.81 (1H, m), 6.84-6.89 (2H, m), 7.31 (1H, t, J = 8.0 Hz), 7.46 (1H, brs).

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Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2530078; (2012); A1;,
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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. 85363-04-8, name is N-(tert-Butoxycarbonyl)-2-aminoacetonitrile, A new synthetic method of this compound is introduced below., Safety of N-(tert-Butoxycarbonyl)-2-aminoacetonitrile

General procedure: A 2-acylamidoacetonitrile was prepared similarly at room temperature, using an acid chloride as a starting compound. To a solution of the compound thus obtained (3 mmol) in dry methanol (50 mL) at room temperature under N2 atmosphere was added L-cysteine methyl ester hydrochloride (770 mg, 4.5 mmol) and triethylamine (0.63 mL, 4.5 mmol). The resulting mixture was stirred for 3 h and evaporated to dryness. The residue was taken up in CH2Cl2 and washed with saturated NaHCO3 solution and brine. The organic extract was dried over sodium sulfate, filtered, evaporated, and purified by column chromatography (silica gel, hexane/ethyl acetate, 5:1) to give a methyl ester of compounds 14 – 17. Precooled LiOH (0.9 mL, 1 N, 0.9 mmol) was added to the methyl ester (1.0 mmol) in methanol (5 mL) at 0 oC. The suspension was stirred for 1 h at room temperature, diluted with acetone (20 mL) to precipitate the product. The white powder was filtered and dried to give compounds 14 – 17.

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:
Article; Chen, Pinhong; Horton, Lori B.; Mikulski, Rose L.; Deng, Lisheng; Sundriyal, Sandeep; Palzkill, Timothy; Song, Yongcheng; Bioorganic and Medicinal Chemistry Letters; vol. 22; 19; (2012); p. 6229 – 6232;,
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Adding a certain compound to certain chemical reactions, such as: 21524-39-0, name is 2,3-Difluorobenzonitrile, 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 21524-39-0, SDS of cas: 21524-39-0

Method A (standard SNAr/CsF ) To a soln. of C-1 (1 eq) and BB-8 (1 to 1.1 eq) in DMSO (3 mL/mmol) was added CsF (2 eq). The rxn mixture was heated at a given temperature for a given time (see Table 26) and was partitioned between EtOAc and water. The org. phase was washed with water (3x) and with brine, dried over MgSCh and concentrated in vacuo. The crude was purified by CC using Hept/EtOAc.

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Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; FROIDEVAUX, Sylvie; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; (188 pag.)WO2019/141803; (2019); A1;,
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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 66389-80-8 as follows. category: nitriles-buliding-blocks

Synthesis of SiR-Tz (FIG. 8) (0148) 4-Cyanobenzylamine HCl was Boc-protected with Boc-anhydride. The Boc-protected amine was converted to the tetrazine 8 (Yang, et al., 2012, Angew. Chem., Int. Ed. 51:5222-5225). The Boc-group of tetrazine 8 was removed by treating the compound with a 1:1 mixture of TFA and dichloromethane and immediately coupled with SiR-OH (Lukinavicius, et al., 2013, Nature Chem. 5:132-139) mediated by TBTU and iPr2NEt.

According to the analysis of related databases, 66389-80-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yale University; ERDMANN, Roman; SHRADER, Alanna Schepartz; TOOMRE, Derek; (34 pag.)US2016/115180; (2016); A1;,
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Synthetic Route of 914250-82-1, 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 914250-82-1 as follows.

3-bromo-2-chlorobenzonitrile (500 mg, 2.30 mmol), bis(pinacolato)diboron (741 mg, 2.92 mmol), [l,l ‘-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with DCM (93.9 mg, 115 muiotaetaomicron) and potassium acetate (689 mg, 7.03 mmol) were weighed into a 40 ml vial equipped with a teflon/rubber screw cap and a stir bar. The reaction vessel was purged 3 times with N2, dioxane (degassed) (18.4 mL) was added against N2 and the headspace of the reaction was purged 3 more times with N2. The reaction was placed into a heating block preheated to 85 C and stirred vigorously at this temperature for 2.5 hours. After cooling to room temperature the mixture was filtered over celite, the filtrate was evaporated to dryness and the crude product was purified by column chromatography (0 – 99% EtO Ac/heptanes) to give 370 mg (61%) of the desired product. LC-MS (ESI) m/z: [M + H] calculated for CI3HI5BC1N02: 264.10, found 263.8.

According to the analysis of related databases, 914250-82-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; REVOLUTION MEDICINES, INC.; JOGALEKAR, Ash; WON, Walter; KOLTUN, Elena S.; GILL, Adrian; MELLEM, Kevin; AAY, Naing; BUCKL, Andreas; SEMKO, Christopher; KISS, Gert; (496 pag.)WO2018/13597; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 50635-21-7, name is o-Tolyloxyacetonitrile, 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 50635-21-7, Safety of o-Tolyloxyacetonitrile

Preparation example 19: 2-(2-Methylphenoxy)acetamidine The above-titled product was obtained in the same method as in Preparation example 7 using 2-(2-methylphenoxy)acetonitrile instead of 4-chlorophenoxy-acetonitrile. 1H-NMR (DMSO-d6) delta: 4.92(2H, s), 6.85(1H, d, J=8.5Hz), 6.91-6.96(1H,m),7.16-7.22(2H, m), 9.15(3H, brs). Mass (EI, m/z): 164(M+).

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Reference:
Patent; Meiji Seika Kaisha, Ltd.; EP1142881; (2001); 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. 41429-22-5, name is 2-(2-(Difluoromethoxy)phenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C9H7F2NO

[0607] To a solution of [2-(difluoromethoxy)phenyl]acetonitrile (5.00 g, 27.3 mmol) in THF (25 ml) under argon was added gradually while stirring, at -78C., a 2 M solution of LDA in THF (16 ml, 33 mmol). The mixture was allowed to come to 0C. and, after 15 min, cooled back down again to -78C. Subsequently, a solution of tert-butyl 3-bromopropanoate (5.2 ml, 33 mmol) in THF (10 ml) was slowly added dropwise thereto at -78C. while stirring. Stirring of the mixture was continued overnight, in the course of which the cooling bath (dry ice/acetone) was allowed to come gradually to RT. Subsequently, water and ethyl acetate (100 ml of each) were gradually added at about 0C. to the mixture, which was agitated. After phase separation, the aqueous phase was extracted once with ethyl acetate (100 ml). The combined organic phases were washed once with saturated aqueous sodium chloride solution (150 ml), dried over sodium sulfate, filtered and concentrated, and the residue was taken up in dichloromethane and purified by flash column chromatography (100 g silica gel Biotage Snap-Cartridge Ultra, cyclohexane/ethyl acetate gradient 93:7?7:3, Isolera One). The combined target fractions were concentrated and the residue was dried under reduced pressure. This gave 3.85 g (83% purity, 38% of theory) of the title compound. [0608] LC-MS (Method 1): Rt=2.10 min; MS (ESIpos): m/z=312 [M+H]+

The synthetic route of 41429-22-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; Bayer Pharma Aktiengeseiisehaft; BECK, Hartmut; KAST, Raimund; MEININGHAUS, Mark; DIETZ, Lisa; FUERSTNER, Chantal; STELLFELD, Timo; ANLAUF, Sonja; VON BUEHLER, Clemens-Jeremias; BAIRLEIN, Michaela; ANLAHR, Johanna; MUENSTER, Uwe; TERJUNG, Carsten; JOERISSEN, Hannah; HAUFF, Peter; MUELLER, Joerg; DROEBNER, Karoline; NAGEL, Jens; (220 pag.)US2020/31775; (2020); A1;,
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191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile, 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. Computed Properties of C8H6FNO

Pyrazolospiroketone Preparation 11; 2-Methoxy-4-(3′-methyl-7′-oxo-6′.7′-dihvdro-2’H-spirorpiperidine-4,5′-pyranor3.2-clPyrazol1-2′-; To a solution of 4-fluoro-2-methoxybenzonitrile (100 g, 0.662 mol) in ethanol (0.66 L) was added hydrazine monohydrate (331 g, 0.321 L, 6.62 mol). The mixture was heated at reflux overnight. The reaction was cooled to room temperature, diluted with water (750 mL), stirred for 1.5 hours and the resulting solids were collected by filtration. The solids were rinsed with water (2 x 250 mL) and air dried for 3 hours. The solids were then dried in a vacuum oven at 45 QC. The material was dissolved in dioxane (2 L) and HCI gas was bubbled through for 30 minutes. The resulting solids were filtered and washed with methyl tert-butyl ether (2 x 1 L). The solids were air dried for 1 hour and the resulting solids were dried in a vacuum oven at 45 QC to provide -hydrazino-2-methoxybenzonitrile hydrochloride (115.6 g, 87.5%).

The synthetic route of 191014-55-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER, INC.; WO2009/144554; (2009); A1;,
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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. 50743-32-3, name is 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 50743-32-3

REFERENCE EXAMPLE b 1 In carbon tetrachloride (300 ml) was suspended 6-isopropyl-4-oxo-4H-1-benzopyran-3-carbonitrile (10.65 g). To the suspension was added N-bromosuccinimide (8.90 g). The mixture was subjected to reflux for two hours under irradiation of infrared ray lamp (Toshiba, 100 V, 375 WR). The resultant was then cooled to room temperature, followed by removal of insolubles by filtration. The filtrate was concentrated under reduced pressure. The concentrate was dissolved in ethyl acetate (150 ml), which was washed with water three times, dried and concentrated. The precipitating crystals were collected by filtration to give 6-(1-bromo-1-methylethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile as colorless prisms (7.0 g). Melting point: 115-117 C.

According to the analysis of related databases, 50743-32-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US4716167; (1987); A;,
Nitrile – Wikipedia,
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