Category: nitriles-buliding-blocks

Application of 7357-70-2, 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. 7357-70-2, name is 2-Cyanothioacetamide, This compound has unique chemical properties. The synthetic route is as follows.

N-Methylmorpholine (10 drops) was added to a mixture of cyanothioacetamide 1 (4.00 g, 0.04 mol) [5] and indole-3-carbaldehyde (5.80 g, 0.04 mol) in 50 mL of 96% EtOH. The mixture was refluxed for 5 min with stirring. After cooling the resulting red solution, the precipitate formed, which was filtered off after 24 h, washed with diethyl ether, and dried. Yield 5.50 g (61%), yellow powder, mp 169-172C (EtOH) (mp 174-176C [37]). IR spectrum, nu, cm-1: 3320 (N-H), 2215 (C?N). 1H NMR spectrum, delta, ppm: 7.15-7.22 m (3H, H-Ar), 7.88-7.93 m (1H, H-Ar), 8.54 d (1H, H2, J = 2.9 Hz), 8.64 s (1H, CH=), 9.01 br.s (1H, CSNH2), 9.44 br.s (1H, CSNH2), 12.24 br.s (1H, NH). 13C NMR spectrum, deltaC, ppm: 104.1 (C-C?N), 108.2 (C3, indole), 115.0 (CH-Ar), 116.9 (C?N), 120.5 (CH-Ar), 122.9 (CH-Ar), 123.8 (CH-Ar), 129.7 (C-Ar), 135.0 (C-Ar), 138.7 (C-Ar), 142.1 [CH=C(C?N)], 190.3 (C=S). Found, %: C 63.57; H 4.12; N 18.33. C12H9N3S. Calculated, %: C 63.41; H 3.99; N 18.49.

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

Reference:
Article; Dotsenko; Krivokolysko; Krivokolysko; Frolov; Russian Journal of General Chemistry; vol. 88; 4; (2018); p. 682 – 688; Zh. Obshch. Khim.; vol. 88; 4; (2018); p. 599 – 605,7;,
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Synthetic Route of 261762-98-5, 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. 261762-98-5, name is 3-Chloro-2-fluorophenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows.

1-Bromomethyl-3-chloro-2-fluoro-benzene (10.00 g, 44.80 mmol) and KCN (5.80 g, 89.07 mmol) were mixed in DMF and the resulting reaction mixture was stirred at 75 C. for 2 days. The reaction mixture was cooled to room temperature, and water was added. The mixture was extracted with Et2O (3¡Á300 mL). The combined organic phases were washed with H2O (2¡Á200 mL) and brine (1¡Á200 mL), then dried over MgSO4 and concentrated. The crude nitrile was taken up in water and KOH (5.00 g, 89.11 mmol) was added. The resulting mixture was refluxed for 14 hours. After cooling to room temperature, the reaction mixture was diluted with water and washed with Et2O (2¡Á150 mL). The aqueous layer was acidified with concentrated HCl and was extracted with Et2O (3¡Á300 mL). The combined organic phases were washed with H2O (2¡Á200 mL) and brine (1¡Á200 mL), then dried over MgSO4 and concentrated to afford the title acid.

The chemical industry reduces the impact on the environment during synthesis 3-Chloro-2-fluorophenylacetonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Allerghan, Inc.; US2008/194650; (2008); A1;,
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Related Products of 77-57-6,Some common heterocyclic compound, 77-57-6, name is 1-Phenylcyclopentanecarbonitrile, molecular formula is C12H13N, 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 1 -phenyl- l-cyclopentanecarbonitrile (1.500 mL, 8.76 mmol, Acros Organics USA) in MeOH (40 mL) was added a solution of palladium, 10wt. % on activated carbon (93 mg, 0.876 mmol, Aldrich) in EtOAc (0.5 mL) and concentrated HCl (0.4 mL). The reaction mixture was stirred at room temperature under H2 (42 psi) overnight. The reaction mixture was filtered through celite, washed the filter-cake with MeOH. The combined filtrates were concentrated and H2O was added to the residue. The aqueous solution was extracted with EtOAc. The aqueous layer was basified (pH >10) using saturated aqueous NaHCtheta3 and extracted with EtOAc. The combined organic extracts were dried over MgSO4, concentrated, and dried in vacuum to give (l-phenylcyclopentyl)methanamine as light yellow oil, which was used in the next step without purification.

The synthetic route of 77-57-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2009/137404; (2009); A1;,
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2042-37-7, name is 2-Bromobenzonitrile, 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. Product Details of 2042-37-7

Intermediate Example Int3.1(6-Bromo-[1 ,2,4]triazolo[1 ,5-a]pyridin-2-yl)-o-cyanophenyl-amineTo a stirred solution of 213 mg (1 mmol) Int1.2 in THF (2.5 mL) was added 364 mg (2 mmol, 2 eq) 2-Brombenzonitril, 183 mg (0.2 mmol, 0.2 eq) Pd2(dba)3, 374 mg (0.6 mmol, 0.6 eq) rac-BINAP and 240 mg (2.5 mmol, 2.5 eq) NaOtBu at room temperature in a microwave reactor. The solution was heated at 150 C for 50 min under microwave irradiation. After cooling, the solution was filtered and evaporated. Subsequent purification by by preparative reverse phase HPLC gave 186 mg (59 %) of the title compound.1H-NMR (300 MHz, d6-DMSO): delta = 9.56 (1H, s), 9.16 (1 H, s), 7.91 (1 H, d), 7.72 (1 H, d), 7.70 (1 H, d), 7.62 (1H, dd) 7.54 (1 H, d), 7.15 (1H, dd) ppm. UPLC-MS: RT = 1.15 min; m/z (ES+) 315.2 [MH+]; required MW = 314.2.

The synthetic route of 2042-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; KOPPITZ, Marcus; KOSEMUND, Dirk; SCHIROK, Hartmut; BADER, Benjamin; LIENAU, Philip; WENGNER, Antje; BRIEM, Hans; HOLTON, Simon; SIEMEISTER, Gerhard; PRECHTL, Stefan; BOeMER, Ulf; WO2011/63908; (2011); 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 67515-59-7 as follows. category: nitriles-buliding-blocks

To a solution of 4-fluoro-3-(trifluoromethyl)benzonitrile (10 g), /-PrOH (8.15 mL) in tetrahydrofuran (THF) (90 mL) stirred under nitrogen at -10 C was added solid NaH (3.46 g) portionwise during 30 min. The reaction mixture was stirred at -10 C for 6 h. The reaction mixture was quenched with water, partitioned between ether (.100 mL) and water (50 mL).The organic phase was dried over magnesium sulphate and evaporated in vacuo to give the crude product 4-[(1-methylethyl)oxy]-3- (trifluoromethyl)benzonitrile (D10) (15 g).

According to the analysis of related databases, 67515-59-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; DENG, Guanghui; LIN, Xichen; REN, Feng; ZHAO, Baowei; WO2011/134280; (2011); A1;,
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Synthetic Route of 185836-35-5,Some common heterocyclic compound, 185836-35-5, name is 4-(Benzyloxy)-2-fluorobenzonitrile, molecular formula is C14H10FNO, 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.

16.1. 6-(Phenylmethoxy)-1,2-benzisothiazol-3-amine A mixture of 13.2 g (0.058 mol) of 2-fluoro-4-(phenylmethoxy)benzonitrile and 1.85 g (0.058 mol) of sulphur in 15 ml (0.58 mol) of ammonia and 50 ml of methylglycol is brought to 100 C. in an autoclave over 5 hours. The methylglycol is subsequently evaporated off under reduced pressure. The mixture is taken up in dichloromethane, the insoluble material is filtered off, and then the solvent is evaporated off under reduced pressure. The product is purified by chromatography on a silica column with cyclohexane and ethyl acetate in proportions of 60:40. Subsequently, a second purification by chromatography on a silica column with a mixture of diisopropyl ether and methanol in proportions of 99:1 leads to 1.7 g of product. Melting point: 158 C.

The synthetic route of 185836-35-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Synthelabo; US5843975; (1998); A;,
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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. 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C8F4N2

SYNTHESIS EXAMPLE 2 Synthesis of 3-(2,6-dibromo-4-methylphenoxy)-4,5-bis(2,5-dichlorophenoxy)-6-fluorophthalonitrile In a four-neck separable flask having an inner volume of 500 ml, 60 g (0.30 mol) of tetrafluorophthalonitrile, 41.8 g (0.72 mol) of potassium fluoride, and 160 ml of acetone were placed. Further, in a dropping funnel attached thereto, 97.8 g (0.60 mol) of 2,5-dichlorophenol and 110 ml of acetone were placed. The 2,5-dichlorophenol/acetone mixed solution was added dropwise from the dropping funnel to the flask over a period of about two hours while kept stirred at -1¡ã C. The stirring was subsequently continued for about two hours. Thereafter, the contents of the flask were stirred overnight, with the reaction temperature thereof slowly raised to room temperature. Then, to this flask, 79.8 g (0.30 mol) of 2,6-dibromo-4-methylphenol, 20.9 g (0.36 mol) of potassium fluoride, and 15.0 ml of acetone were charged and the mixture was kept stirred at 40¡ã C. for 10 hours. The reaction solution was cooled and filtered. The filtrate was distilled by a rotary evaporator to expel the acetone and was recrystallized from methanol. The produced crystals were separated by filtration and vacuum dried to afford 176.8 g of 3-(2,6-dibromo-4-methylphenoxy)-4,5-bis(2,5-dichlorophenoxy)-6-fluorophthalonitrile (yield: 80.5 mol percent).

The synthetic route of 1835-65-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Shobukai Co., Ltd.; US6323340; (2001); B1;,
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These common heterocyclic compound, 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, 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. category: nitriles-buliding-blocks

Step 7 : Preparation of N1(cyanomethyl)-N2{(1S)-2,2,2-trifluoro-1-[4′-(methylsulfonyl)-1,1′- BIPHENYLLETHYL}-L-LEUCINAMIDE; To a DMF (200 ML) solution of the acid from Step 7 (9 g) was added benzotriazol-1- yloxytris (dimethylamino) phosphonium hexafluorophosphate (11.6 g), aminoacetonitrile hydrochloride (3.94 g) and the mixture was cooled to 0 C. Triethylamine (9.9 ML) was added dropwise and the mixture warmed to room temperature and stirred for 16 hours. It was poured into ice and saturated aqueous sodium bicarbonate and extracted with diethyl ether (3 X 100 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo. The residue was purified by chromatography on SIO2USING ethyl acetate and hexanes (1: 1). The title compound was then stirred in diethyl ether for 16 hours, filtered and dried (mp 140.5 C). 1H NMR (CD3COCD3) 6 8.0 (2H, d), 7.95 (2H, d), 7.8 (2H, d), 7.65 (2H, d), 4.35-4. 45 (1H, m), 4.1-4. 2 (2H, m), 3.45-3. 55 (1H, m), 3.15 (3H, s), 2.65-2. 7 (1H, m), 1.85-1. 95 (1H, m), 1.4-1. 6 (2H, m), 0. 85-0. 95 (6H, m).

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

Reference:
Patent; MERCK FROSST CANADA & CO.; WO2005/19161; (2005); A1;,
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Related Products 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.

General procedure: Method I. A mixture of Py (4.4 ml) and AcOH (3.0 ml) was stirred and treated by the addition of 5-aminoazole1a-h (0.01 mol) and (2E)-(3-morpholin-4-yl)-acrylonitrile (2) (1.38 g, 0.01 mol). The obtained mixture was refluxed at 150C for 5 h. After refluxing, the mixture was cooled. The precipitate that formed was filtered off, washed with a small amount of EtOH, and dried. Method II. A solution (or suspension) of the appropriate aminoazole 1a-h (0.01 mol) in solvent (15 ml) (EtOH in the case of compound 3a, dioxane in the case of compounds 3b-h) was stirred at 50C and treated by adding 3,3-diethoxypropionitrile (4) (1.5 ml, 0.01 mol), then 36% HCl solution (0.86 ml, 0.01 mol). The reaction mixture was refluxed for 2.5-3 h, the suspension (or solution) was cooled to room temperature, and the target product was isolated by the method indicated for each particular compound.

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

Reference:
Article; Gazizov, Denis A.; Fedotov, Victor V.; Gorbunov, Evgeny B.; Ulomskiy, Evgeny N.; Yeltsov, Oleg S.; Rusinov, Gennady L.; Rusinov, Vladimir L.; Chemistry of Heterocyclic Compounds; vol. 55; 6; (2019); p. 573 – 577; Khim. Geterotsikl. Soedin.; vol. 55; 6; (2019); p. 573 – 577,5;,
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Synthetic Route of 1953-99-7, 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. 1953-99-7 name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, 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.

Five grams of 3,4,5,6-tetrachlorophthalonitrile, 3.25 grams of 2-bromophenol, 3.9 grams of K2CO3, and 25 milliliters of N, N-dimethylformamide were placed in a 100 milliliter flask , Followed by stirring while heating at 70 ¡ãC. EIA (ethyl acetate) was used for extraction when the reaction was completed. After extraction, the resultant was concentrated to obtain a solid. In this context, the solid obtained is dissolved in a small amount of dichloromethane, washed several times with hexane, filtered and dried in vacuo to give 3,4,6-dichloro-5- (2-bromo-phenoxy ) -phthalonitrile.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Sanxing SDI Co., Ltd.; Zheng Yishu; Xu Huiyuan; Xin Mingye; Shen Xianxiong; Zheng Zhouhao; Han Guishi; (48 pag.)CN107522704; (2017); A;,
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