Month: July 2021

Synthetic Route 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 500912-18-5, A common heterocyclic compound, 500912-18-5, name is 2-(2-Fluoro-6-methoxyphenyl)acetonitrile, molecular formula is C9H8FNO, 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.

First, sodium bis(trimethylsilyl) amide (1.0 M tetrahydrofuran solution) (1.6 mL) was added dropwise to a solution of 2-(2-fluoro-6-methoxyphenyl)acetonitrile (86 mg) in tetrahydrofuran (2.4 mL) under ice cooling, and the mixture was stirred at the same temperature for 30 minutes. N-benzyl-bis(2-chloroethyl)amine hydrochloride (140 mg) was added to the resultant solution, followed by reflux for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then was dried with anhydrous magnesium sulfate. the solvent was removed by evaporation under reduced pressure. The obtained residue was purified by silica gel column chromatography (diethylether/n-hexane = 50/50) to obtain 1-benzyl-4-(2-fluoro-6-methoxyphenyl)piperidine-4-carbonitr ile (132 mg). 1H-NMR (400MHz, CDCl3) delta: 2.28-2.37(m,2H),2.43-2.50(m,2H),2.50-2.59(m,2H),2.89-2.98(m ,2H),3.58(s,2H),3.91(s,3H),6.67(ddd,J=12.9,8.4,1.2Hz,1H),6. 74(d,J=8.3Hz,1H),7.21-7.29(m,3H),7.29-7.36(m,4H).

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; RIKEN; Japanese Foundation For Cancer Research; YOSHIDA, Minoru; SEIMIYA, Hiroyuki; OKUE, Masayuki; YASHIRODA, Yoko; SHIRAI, Fumiyuki; TSUMURA, Takeshi; KANO, Yuko; WASHIZUKA, Kenichi; YOSHIMOTO, Nobuko; KOUDA, Yasuko; FUKAMI, Takehiro; CHIKADA, Tsubasa; WATANABE, Takashi; (261 pag.)EP3480198; (2019); A1;,
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Reference of 127946-77-4,Some common heterocyclic compound, 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, molecular formula is C4H7ClN2, 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.

(1S,4S)-5 -(1 -Methyl-cyclopropanecarbonyl)-2-oxa-5-aza-bicyclo [2.2.1]heptan-3-one (100 g, 512 mmol), 1-amino-cyclopropanecarbonitrile hydrochloride (62.0 g, 523 mmol), and sodium 2-ethylhexanoate (97%, 96.5 g, 563 mmol) were dissolved in water (500 mL). The mixture was stirred for 16 h at 50C. After cooling to room temperature, dichloromethane (500 mL) was added, the mixture was acidified by addition of hydrochloric acid (25% m/m, 13.8 mL, 106 mmol), and sodium chloride (120 g) was added. The mixture was stirred for 1 h, phases were separated, the aqueous layer was extracted with dichloromethane (3 x 330 mL) and the combined organic extracts were concentrated in vacuo to a volume of ca. 1.1 L. Ethyl acetate (1.1 L) was added, the mixture was concentrated in vacuo to a volume of ca. 1 L and heptane (1 L) was added within 30 mm. The resulting suspension was stirred for 2 h at 2C, filtered, the precipitate was washed with cold ethyl acetate / heptane 1:1 (v/v, 340 mL) and heptane (340 mL) and dried in vacuo to afford the title compound as light yellow crystals (129.4 g, 90%). MS (ESI & APCI): m/z = 278.1 [M + H]. 1H NMR (CDC13, 600 MHz): oe 0.60-0.65 (m, 2H), 0.89-0.92 (m, 1H), 0.95-0.98 (m, 1H), 1.20-1.26 (m, 2H), 1.33 (s, 3H), 1.50-1.57 (m, 2H), 2.13 (ddd,J 5.0 Hz, 9.0 Hz, 14.1 Hz, 1H), 2.39 (br d, J= 14.3 Hz, 1H), 3.76 (dd, J 4.3 Hz, 11.6Hz, 1H), 3.85 (d, J 11.6 Hz, 1H), 4.48- 4.53 (m, 1H), 4.57 (d, J 9.0 Hz, 1H), 4.70 (br s, 1H), 7.92 (br s, 1H).

The synthetic route of 127946-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BARTELS, Bjoern; BLISS, Fritz; CUENI, Philipp; PFLEGER, Christophe; ZUTTER, Ulrich; WO2013/68434; (2013); 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. 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H6FN

1,2-Dichloroethane (151 kg) was charged to a suitable vessel along with 4-cyano-2-fluorotoluene (24 kg) and AIBN (2 kg). The mixture was heated to 7074 C. Once the batch temperature reached 70 C., N-bromosuccinimide (47.4 kg) was added in portions at the rate of 12 kg/h, maintaining the temperature at 7074 C. (it is important to control addition rate to avoid exothermic reaction). The mixture was sampled via GC detection after 24 kg of N-bromosuccinimide was added, and the reaction was heated at 70-74 C. until complete reaction was observed. The mixture was cooled to 0-5 C. and allowed to stand for 2 additional hours. The mixture was filtered, and the cake was washed with MTBE (24 kg). The filtrate was washed with water (3×65 kg). The organic layer was dried with sodium sulfate (10.3 kg) for 6 hours, filtered and the cake was washed with MTBE (24 kg). The solution was evaporated under reduced pressure, ethanol (12 kg) was added and the mixture was heated to 40-45 C., then cooled slowly to 0-5 C. while stirring to crystallize. The mixture was filtered and the cake was washed with cold ethanol (5 kg). The crude solid was recrystallized from petroleum ether, filtered and washed with petroleum ether (10 kg), giving the title compound 4-(bromomethyl)-3-fluorobenzonitrile as an off white solid (21 kg, 55% yield). 1H NMR (300 MHz, CDCl3) delta ppm 4.46-4.50 (m, 2H) 7.36 (dd, J=8.85, 1.32 Hz, 1H) 7.44 (dd, J=7.91, 1.32 Hz, 1H) 7.52 (dd, J=7.91, 7.16 Hz, 1H). 13C NMR (75 MHz, CDCl3) 8 ppm 23.65 (d, J=4.60 Hz, 1C) 113.76 (d, J=9.77 Hz, 1C) 117.09 (d, J=2.87 Hz, 1C) 119.44 (d, J=24.71 Hz, 1C) 128.44 (d, J=4.02 Hz, 1C) 130.66-130.81 (s, 1C) 130.81-131.06 (s, 1C) 132.18 (d, J=3.45 Hz, 1C) 159.86 (d, J=254.03 Hz, 1C). IR: (KBr) 3088, 3077, 3040, 2982, 2250, 1571, 1508, 1439, 1248 cm-1.Anal. Calcd for C8H5BrFN: Calc. C, 44.89; H, 2.35; N, 6.54; F, 8.88. Found: C, 44.94; H, 2.73; N, 6.56; F, 8.73.

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 170572-49-3.

Reference:
Patent; Bristol-Myers Squibb Company; US2010/240719; (2010); 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. 623-00-7, name is 4-Bromobenzonitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

4-[(4-Cyanophenyl)(hydroxy,)methylJbenzonitrile (lOu, Q1=CN, Q4=CN). To a solution ofiPrMgCl LiCl complex 1.3 M in THF (10.5 ml) at -15C 4-bromobcnzonitrilc (1.4 g, 7.6 mmol) in THF (4 ml) was added dropwise over 15 mm. The brown solution was stirred for 30 mm at -15 C and 1.5 h at it The solution was added dropwise to a yellowish solution of 4- formylbenzonitrile (1.0 g, 7.6 mmol) in THF (4 ml) over 10 mm at -15C. After 1 h stirring at 0C the light green solution was quenched with aq. sat. NH4C1 (20 ml), TBME (30 ml) andwater (20 ml) were added. After separation of the organic layer the inorganic phase was extracted with TBME (2 x 20 ml). The organic layers were washed with aq. sat. NaC1, combined, dried over Na2SO4 and concentrated at reduced pressure. To the liquid crude product (2 g) EtOAc/hept 1:2 was added. An insoluble pale yellow solid (0.54 g) was filtered off, dissolved in diethylether and precipitated with pentane to afford a pale yellow solid lOu(0.49 g, 27.5%). The mother liquor was concentrated at reduced pressure and was purified by silica gel flash chromatography (EtOAc/hept 1:2) to afford a pale yellow solid lOu (0.23 g, 13%).

The synthetic route of 623-00-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALLOCYTE PHARMACEUTICALS AG; BREITENSTEIN, Werner; HUERZELER, Marianne; KELLY, Terence; MANCUSO, Riccardo; SCHNEIDER, Gisbert; WEITZ-SCHMIDT, Gabriele; WO2015/189265; (2015); 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. 17626-40-3, name is 3,4-Diaminobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 17626-40-3

To a solution of 1,2-diamino-4-cyanobenzene (1.00 mL, 7.51 mmol) in tetrahydrofuran (5 mL) was added 1 , 1 ‘-carbonyldiiimidazole (1.22 g, 7.51 mmol). The reaction was stirred at ambient temperature for one hour, concentrated, then triturated with water. ‘The brown precipitate was collected by vacuum filtration to provide 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbonitrile as a brown powder. MS (ESI, pos. ion) m/z: 160.2 j i j

According to the analysis of related databases, 17626-40-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; BARTBERGER, Michael D.; CHAKKA, Nagasree; GAO, Hua; GUZMAN-PEREZ, Angel; HORNE, Daniel B.; HUA, Zihao; KIEFFER, Madeleine; LIN, Daniel C. H.; MILGRAM, Benjamin Charles; PANTELEEV, Jane; SCHENKEL, Laurie; STELLWAGEN, John; WEISS, Matthew; WHITE, Ryan D.; ZHAO, Wei; (345 pag.)WO2019/79578; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 31643-49-9, name is 4-Nitrophthalonitrile, 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 31643-49-9, Recommanded Product: 4-Nitrophthalonitrile

Under inert gas (N?), 4~Mtro~o~phth.ak>nitrile (9.2 g), phenol (5.0 g), .2CO3 (7.3 g) and DMSO (40 mL) were added into a flask, and were stirred and reacted at room temperature for 48 hrs., then heated to 60 C and reacted for 2 hrs. After cooled down, the reaction mixture was filtered and the resulted yellow solid was dried to obtain 11.6 g of Compound 1.

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; ZHEJIANG BETA PHARMA INCORPORATION; KANG, Xinshan; LONG, Wei; ZHANG, Jianxi; HU, Yunyan; WANG, Yinxiang; WO2013/13609; (2013); 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. 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

2-Fluoro-5-nitrobenzonitrile (50 g, 0.3 mol) was dissolved in 500 ml of dimethylsulfoxide and potassium carbonate (49.7 g,0.36 mol) and sodium methanesulfinate (36.7 g, 0.36 mol) was added.Heated to 100 C overnight reaction, TLC detection (EpsilonAlpha: PE =1: 1), the reaction is over.After the reaction solution was poured into 100 mL of water, no solid was precipitated, and extracted with EA (250 mL * 4). The combined EA phases and sulfuric acidSodium dried, concentrated by column chromatography to give a yellow brown solid (5g, yield 7.4%);Intermediate 5g suspended in 100mL of water, add10 mL of concentrated hydrochloric acid was added and the mixture was stirred for 30 minutes. TLC (EA: PE = 1: 1) was performed. The reaction was completed and the reaction mixture was extracted with DCMTake, merge DCM phase three times,Saturated brine (100mL * l), the organic phase was dried over sodium sulfate, concentrated to give a solid which was purified by column chromatography to give a yellow powder (3.00g, 7.3 ·)

The synthetic route of 17417-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Qidong Shaoyuan Chemical Technology Co., Ltd.; Li Shaobo; Wu Yong; Gai Hongguang; Xie Chunhui; Guo Meng; (5 pag.)CN104744429; (2016); B;,
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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. 64248-62-0, name is 3,4-Difluorobenzonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 64248-62-0

A well dried 5 L, four necked round bottom flask fitted with over-head stirrer was charged a solution of diisopropyl amine (174.6 mL, 2.3 eq, 826.7 mmol) in THF (400 mL) and cooled to -78C. It was added n-butyllithium (496 mL, 2.3 eq, 1240.1 mmol, 2.5 M solution in hexane) at -78C under nitrogen atmosphere and stirred for 1 h. To the resulting LDA solution was added a mixture of N- nitrosodimethylamine 2 (87.7 g, 2.2 eq, 1 186.1 mmol) and 3,4- difluorobenzonithle (75 g, 1 eq, 539.1 mmol) in THF (1000 mL). The reaction mixture was stirred at -78C for 1 h and then slowly warmed to RT and stirred for additional 4h at RT. The reaction mixture was quenched by the addition of saturated aq. ammonium chloride solution (300 mL), extracted with ethyl acetate (3*300 mL). The combined organic extracts were washed with brine (2*200 mL), dried over anhydrous sodium sulphate and evaporated to afford crude (1 18 g) as a brownish gum. The crude material was purified by column chromatography by using silica gel (60-120 mesh) using 30% ethyl acetate in hexane as eluent, to afford 4-(3,4-difluorophenyl)-1 -methyl-1 H-1 ,2,3-triazole 3 (30 g, 28% yield) as pale yellow solid. 1H NMR (400 MHz, CDCl3): delta 7.73 (s, 1 H), 7.71 -7.64 (m, 1 H), 7.57-7.51 (m, 1 H), 7.28-7.19 (m, 1 H), 4.18 (s, 3H).

The synthetic route of 64248-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANIONA APS; LARSEN, Janus Schreiber; GUSTAFSSON, Magnus; JESSEN, Carsten; WO2014/1278; (2014); 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. 939-80-0, name is 4-Chloro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Chloro-3-nitrobenzonitrile

General procedure: 0.5 mmol nitrobenzene, 4.0 mmol TBH (70%. aq. soln.), 40 mg Co-Ni/ Lignin catalyst and 10 mL Toluene were added in to an 80 mL autoclave. It was then exchanged with 4.0 MPa H2. The reaction was reacted at 160 C for 36 h under magnetic stirring. Subsequently, the autoclave was cooled to room temperature, and 70 mg biphenyl and 10 mL ethanol were added for quantitative analysis by GC-FID (Agilent 6890A). Purification Procedure: The crude products were subjected to silica gel column chromatography (60, 230-400 mesh supplied by Qingdao Haiyang Chemical and Special Silica Gel Co, Ltd). Eluting with ~75mL of Petroleum Ether, followed by 100:1 (Petroleum Ether:EtOAc).

According to the analysis of related databases, 939-80-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pang, Shaofeng; Shi, Feng; Tetrahedron Letters; vol. 57; 52; (2016); p. 5872 – 5876;,
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