Category: nitriles-buliding-blocks

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. 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., 1813-33-8

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol) and appropriate thiol (RSH, 3.00 mmol),18-crown-6-ether (cat.) and potassium carbonate (2.00 mmol)were dissolved in acetonitrile (3 ml). The mixture was refluxedfor 12 h and then cooled to ambient temperature. The mixturewas quenched by adding water and extracted with EtOAc.Extracted organic compound was dried over MgSO4, filtered, andconcentrated in vacuo. The residue was purified by flash columnchromatography on silica gel using EtOAc/hexane (1:4) eluantcondition. (RSH = CH3CO2(CH2)2SH for 42).

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; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
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179898-34-1, 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. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 3-bromo-5-fluorobenzonitrile (LXVI) (44.0 g, 220.0 mmol, 1.0 eq) was dissolved in THF (30 mL). BH3-Me2S (33.43 g, 440.0 mmol, 2.0 eq) was added to the solution at 20C. Then it was stirred at 80C for 2 h, HC1 (6 N, 100 mL) was added to the mixture slowly at 20C. The mixture was stirred at 80C for 1 h, then it was washed with EtOAc (300 mL). The water phase was basified with 50% aqueous NaOH and it was extracted with EtOAc (300 mL x 3). The combined organic layers were dried over anhydrous Na2504 and concentrated in vacuo to produce (3-bromo-5-fluoro-phenyl)methanamine (LXVII) (24.0 g, 117.62 mmol, 53.5% yield). ?H NMR (CDC13, 300 MHz) ppm 3.86 (s, 2H), 7.01 (d, J=8Hz, 1H), 7.12 (d, J=8Hz, 1H), 7.28 (s, 1H); ESIMS found C7H7BrFN mlz 203.9 (Br79M+H).

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; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (254 pag.)WO2017/23993; (2017); A1;,
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610-66-2, Adding a certain compound to certain chemical reactions, such as: 610-66-2, name is 2-(2-Nitrophenyl)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 610-66-2.

To a solution of 2- nitrophenylacetonitrile (162 mg, 1 mmol) in anhydrous DMSO (5 mL) was added K2C03 (152 mg, 1.1 mmol) and the reaction mixture was stirred for 10 min under nitrogen atmosphere. Butyl iodide (125 //L, 1.1 mmol) was added to the reaction mixture and the stirring was continued for 3 h. Water was added to the reaction mixture and it was extracted with EtOAc (3 x 20 mL). The combined organic layer was dried over Na2S04, concentrated under reduced pressure, and the crude material was purified by silica gel column chromatography (10%> EtOAc/hexanes) to afford compound A2 as a pale yellow oil (174 mg, 80%>). Rf = 0.50 (10%> EtOAc/hexanes).

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, 2-(2-Nitrophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNIVERSITY OF KANSAS; DAVID, Sunil, Abraham; YOO, Euna; SHUKLA, Nikunj; SALYER, Alex, Christopher; BEESU, Mallesh; MALLADI, Subbalakshmi, S.; JONES, Cassandra; WO2015/23958; (2015); A1;,
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151-18-8, A common compound: 151-18-8, name is 3-Aminopropanenitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

At room temperature,To a solution of 4- (2- (1-methyl-1H-pyrazol-4-yl) -5 – ((2- (trimethylsilyl) ethoxy) methyl) -5H-pyrrolo [ 3-b] pyrazin-7-yl) cyclohexanone (15 mg, 0.03 mmol)3-aminopropionitrile (30 [mu] L, 0.41 mmol)Of tetrahydrofuran (4 mL)Was added sodium triacetoxyborohydride (12 mg, 0.05 mmol)Stirred at room temperature for 6 hours,(20 mL), extracted with dichloromethane (20 mL x 3), dried over anhydrous sodium sulfate and concentrated column chromatography (dichloromethane / methanol (v / v) = 10/1) to give 12 mg of a yellow oil, yield: 70.98%.

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

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Bing; Huang Jiuzhong; Zheng Changchun; Zhang Yingjun; Ouyang Luo; Mao Hongfen; Nie Biao; Xu Juan; Chen Hongfen; (137 pag.)CN106336413; (2017); A;,
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17626-40-3,Some common heterocyclic compound, 17626-40-3, name is 3,4-Diaminobenzonitrile, molecular formula is C7H7N3, 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.

Into a 100-mL round-bottom flask, was placed a solution of l,2-bis(4- methoxyphenyl)ethane-l,2-dione (200 mg, 0.74 mmol, 1.00 equiv) in acetic acid (20 mL), 3,4-diaminobenzonitrile (118.2 mg, 0.89 mmol, 1.20 equiv). The resulting solution was stirred for 1 h at reflux in an oil bath. The reaction was then quenched by the addition of water. The solids were collected by filtration and washed with MeOH. This resulted in 205 mg (71%) of 2,3-bis(4-methoxyphenyl)quinoxaline-6- carbonitrile as a yellow solid.LC-MS-PH: (ES, m/z): 368 [M+H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17626-40-3, its application will become more common.

Reference:
Patent; BIOENERGENIX; MCCALL, John, M.; MCKEARN, John; ROMERO, Donnal, L.; CLAIR, Michael; WO2011/28947; (2011); A2;,
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A common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, molecular formula is C8Cl4N2, 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. 1953-99-7.

.60 g (0.015 mol) of sodium hydroxide was added to a solution of 1.64 g (0.0075 mol) of 2,6-dichloro-4-nitroaniline in 40 mL of DMF, followed by addition of 2 g (0.0075 mol) of 3,4,5,6-tetrachlorophthalonitrile under stirring, the mixture was stirred for 5 h after addition at room temperature. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was poured into water and extracted with ethyl acetate, the organic phase was washed with water and saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90¡ã C.)=1:4, as an eluent) to give 2.8 g of compound A-44 as yellow solid, m.p. 188-190¡ã C. [0129] 1H-NMR (300 MHz, internal standard TMS, solvent CDCl3), delta (ppm): 6.76 (s, 1H, NH), 8.31 (s, 2H, Ph-3,5-2H).

The synthetic route of 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY CO., LTD.; SINOCHEM CORPORATION; Liu, Changling; Huang, Guang; Lan, Jie; Hao, Shulin; Li, Zhinian; Li, Huichao; Guan, Aiying; Jiang, Airu; Xu, Ying; US2014/213598; (2014); A1;,
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1080-74-6, A common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, molecular formula is C12H6N2O, 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 intermediate 27 (370 mg, 0.24 mmol) in anhydrous chloroform (26 cm3) is added pyridine (1 .4 cm3, 17 mmol). The mixture is then degassed with nitrogen before 3-(dicyanomethylidene) indan-1 -one (280 mg, 1 .4 mmol) is added. The solution is then further degassed and stirred at 23 C for 20 minutes. The mixture is stirred at 40 C for 2 hours and then the solvent is removed in vacuo. The crude is triturated with ethanol (200 cm3) to produce a heavy suspension which is collected by filtration and the solid washed with acetone (50 cm3). The crude is dissolved in dichloromethane (20 cm3) added precipitated into acetone (250 cm3) to form a suspension. The solid collected by filtration to give compound 90 (437 mg, 96%) as a gray solid. 1H NMR (400 MHz, CDCIs) 8.87 (2H, s), 8.63 – 8.74 (2H, m), 8.13 (2H, s), 7.87 – 7.97 (2H, m), 7.68 – 7.82 (4H, m), 7.23 (8H, d, J 8.8), 6.90 (8H, d, J 9.0), 3.92 (8H, t, J 6.5), 1 .69 – 1 .84 (8H, m), 1 .16 – 1 .52 (72H, m), 0.80 – 0.97 (12H, m).

The synthetic route of 1080-74-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; MORSE, Graham; NANSON, Lana; MITCHELL, William; KROMPIEC, Michal; D’LAVARI, Mansoor; PRON, Agnieszka; (327 pag.)WO2018/65350; (2018); A1;,
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218632-01-0, 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 218632-01-0 as follows.

4-Cyano-2-fluoro-1 -nitrobenzene (300 mg, 0.0018 mol, 1 eq), 1-(tetrahydro-2H-pyran-4- yl)-4~piperidinamine (D9, 330 mg, 0.0018 mol, 1 eq), diisopropylethylamine (350 mg, 0.0027 mol, 1.5 eq), and dimethylformamide (5ml) were combined, heated to 2000C and held for 1 min in a microwave reactor. 100 ml of water was then added and the reaction extracted with 2 x 75 ml dichloromethane. The dichloromethane layers were combined, dried with sodium sulfate, and evaporated to yield the title compound which was used without further purification in the next step. MS (ESI): 331 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 218632-01-0, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/36711; (2007); 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. 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., 25808-30-4

Example 122-Cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(cyanomethylmethyl-carbamoyl)-ethyl]-amide2-Cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(cyanomethylmethyl-carbamoyl)-ethyl]-amide.Prepared according to the procedure outlined in Example 11 substituting Boc-D-alanine for Boc-D-leucine monohydrate and methylaminoacetonitrile hydrochloride for dimethylamine hydrochloride. MS: (M+H)+=327.

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; Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael; US2011/230414; (2011); A1;,
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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. 139152-08-2 name is 4,5-Dichlorophthalonitrile, 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. 139152-08-2

4,5-Dichlorophthalonitrile (1.0g, 5.3mmol) and 13 5-hydroxy-2-methylpyridine (1.4g, 12.4mmol) were dissolved in 15mL of dry 14 N,N-dimethylformamide at 80C under N2. 15 Potassium carbonate (4.5g, 32.6mmol) was added to the reaction solution in 5 portions every 5min. The reaction mixture was heated for 3h at 80C, then cooled to room temperature, and poured into 100mL of 16 ice-water. The title compound was extracted for the reaction liquid using 50mL of 17 CHCl3 at 3 times. After filtration under vacuum, the 18 title compound was obtained as a white powder. Yield, 1.8g (97% (based on 4,5-Dichlorophthalonitrile)). Anal. Calc. for C20H14N4O2: C; 70.17, H; 4.12, N; 16.37. Found: C; 69.93, H; 4.21, N; 16.08%. HR-MS (ESI-TOF): Found 343.1190m/z. [M+H]+ (calcd. for C20H14N4O2 343.1191). 1H NMR (CD2Cl2): delta=8.31 (s, 2H, Ar-H), 7.34 (d, 2H, J=8.4Hz, Ar-H), 7.26 (d, 2H, J=8.4Hz, Ar-H), 7.23 (s, 2H, Ar-H), and 2.57ppm (s, 6H, CH3).

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

Reference:
Article; Fujishiro, Rei; Sonoyama, Hayato; Ide, Yuki; Fujimura, Takuya; Sasai, Ryo; Nagai, Atsushi; Mori, Shigeki; Kaufman, Nichole E.M.; Zhou, Zehua; Vicente, M. Graca H.; Ikeue, Takahisa; Journal of Inorganic Biochemistry; vol. 192; (2019); p. 7 – 16;,
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