Tag: M.W=100-200

Some common heterocyclic compound, 38487-85-3, name is 2-Amino-4-methoxybenzonitrile, molecular formula is C8H8N2O, 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

General procedure: In a 10-mL Schlenk tube, the mixture of 2-aminobenzonitriles 1 (1.0 mmol) and methyl 4,4-difluorobut-2-ynoate 2 (1.5 equiv.) was stirred in MeOH (2.0 mL) at 80 C for 12 h, then DBU (3.0 equiv.) was added and continued to be stirred at 80 C for another 1 h. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography (petroleum ether / ethyl acetate or dichloromethane 10:1 to 1:1 as the eluent) on silica gel to give the desired 2-difluoromethylated quinolines 3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 38487-85-3, its application will become more common.

Reference:
Article; Fan, Zhenhua; Yang, Shanxue; Peng, Xin; Zhang, Cheng; Han, Jing; Chen, Jie; Deng, Hongmei; Shao, Min; Zhang, Hui; Cao, Weiguo; Tetrahedron; vol. 75; 7; (2019); p. 868 – 873;,
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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., COA of Formula: C7H3F2N

A three-necked RB flask was charged with 3,4-difluorobenzonitrile (20 g, 144 mmol) and a mixture of EtOH (190 mL) and water (10 mL). To this homogenous solution were added hydroxylamine hydrochloride (22 g, 317 mg) and TEA (48 mL, 331 mmol). The reaction mixture was stirred at r.t. for 30 min followed by heating to 85 C. for 1 h. TLC indicated the reaction was complete. The mixture was transferred to a 500 mL RB flask, concentrated under reduced pressure to almost dryness, added water (50 mL) and stirred for 30 min. The white precipitates were collected and air dry 12 h before use. LRMS (M+H+) m/z 173.0.

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

Reference:
Patent; LU, Pu-Ping; CHUANG, Chihyuan Grace; MORGAN, Bradley P.; MORGANS, JR., David J.; US2009/198057; (2009); A1;,
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Electric Literature of 6621-59-6, These common heterocyclic compound, 6621-59-6, name is 6-Bromohexanenitrile, 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: A round bottom flask is charged with propargyl derivative of 2-hydroxy benzaldehyde (320 mg, 2 mmol), 4-acetylcoumarin (376.36 mg, 2 mmol), acetyl chloride (2 mL), 2-bromoacetonitrile (1 mL) and BF3.OEt2 (.5ml) and kept under stirring for 3h at room temperature. The progress of the reaction was monitored by TLC analysis at regular intervals. After 3h, the mixture was quenched with cold water. The solid residue separated was collected and purified by passing it through a silica gel column. Elution of the column with petroleum ether (60-80 C) / ethyl acetate (9: 1 v/v) afforded coumarin amidoalkyne 1a.

The synthetic route of 6621-59-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Raj, P. Jithin; Bahulayan; Tetrahedron Letters; vol. 58; 22; (2017); p. 2122 – 2126;,
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Synthetic Route of 796600-15-2, The chemical industry reduces the impact on the environment during synthesis 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile, I believe this compound will play a more active role in future production and life.

Heat 2-chloro-4-fluoro-3-methyl-benzonitrile (144 mg, 0.85 mmol) and 2- . phenyl-pyrrolidine (0.15 g, 1.02 mmol, 1.20 equivalents) in N-methylmorpholine (0.11 ml, 1.02 mmol, 1.20 equivalents) at 150 0C overnight. Allow the reaction mixture to cool to room temperature, dilute with dichloromethane (1 ml), load on silica, and purify by chromatography (12 g silica gel, 0 to 100% ethyl acetate/hexanes over 20 minutes) to obtain 150 mg of an oily residue. Recrystallize from ethyl acetate/hexanes to obtain the title compound (92 mg, 37%). LCMS(APCI+): 297.0 (M+l)+; 1H NMR (400 MHz, CDCl3): delta 7.25 (s, 2H), 7.19 (m, 2H), EPO 6.65 (d, IH), 4.70 (m, IH), 4.06 (m, IH), 3.18 (m, IH), 2.44 (m, IH), 2.43 (s, 3H), 2.12 (m, IH), 1.94 (m, 2H).

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-Chloro-4-fluoro-3-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/124447; (2006); A2;,
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Reference of 621-03-4, 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. 621-03-4, name is 2-Cyano-N-phenylacetamide belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Pyridine was added dropwise with stirring to cyanoacetamide 2a-e(15 mmol) in a round-bottom flask until complete dissolution of the cyanoacetamide. DMAP (18 mg, 0.15 mmol) and mercaptoacetic acid (3.2 ml, 46mmol) were added to the obtained solution. The obtained mixture was refluxed for 12 h in a flask equipped with a reflux condenser,then diluted with 0.5 HCl solution (5 ml).The precipitate of 1,3-thiazolidinone 1 was filtered off and washed with hot MeCN (15 ml). When necessary, the product was additionally purified by refluxing a suspension of thiazolidine in MeCN, followed by hot filtration

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

Reference:
Article; Obydennov, Konstantin L.; Galushchinskiy, Aleksei N.; Kosterina, Marya F.; Glukhareva, Tatiana V.; Morzherin, Yuri Yu.; Chemistry of Heterocyclic Compounds; vol. 53; 5; (2017); p. 622 – 625; Khim. Geterotsikl. Soedin.; vol. 53; 5; (2017); p. 622 – 625,4;,
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Adding a certain compound to certain chemical reactions, such as: 3215-64-3, name is 2-(2,6-Dichlorophenyl)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 3215-64-3, name: 2-(2,6-Dichlorophenyl)acetonitrile

1.4 6-(2,6-dichlorophenyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7-amine.; 5.47 g of 60% NaH was added over 5 minutes to 21 g of the aldehyde obtained in the preceding step dissolved in 240 ml of DMF cooled to 5 C., then 29.05 g of 2,6-dichlorophenylacetonitrile was added over 20 minutes. Stirring was continued for 30 minutes at 5 C. then overnight at ambient temperature. The reaction medium was cooled to 5 C. and 65 ml of a saturated solution of NH4Cl was added followed by 500 ml of a water/ice mixture; a red precipitate was formed which was filtered, washed twice with water, completely drained, washed with ether using 100 ml of chloroform, then again with ether; after drying, a beige solid was obtained. MP=250-253 C., m=29.92 g. The ether and chloroform wash phases were concentrated to dryness and taken up in a little chloroform to which ether had been added: a second quantity of 3.15 g was obtained. Total m=33.07 g.

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-(2,6-Dichlorophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sanofi-aventis; US2007/167469; (2007); A1;,
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Related Products of 33143-29-2,Some common heterocyclic compound, 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, molecular formula is C12H11NO, 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.

Example 4 2,2-Dimethyl-3,4-dihydro-3-(t-butoxycarbonyl)amino-6-cyano-2H-1-benzopyran (E4) A solution of 6-cyano-2,2-dimethyl-2H-1-benzopyran (1.0g) and N,N-dichloro-t-butylurethane (1.1g) in toluene (20 ml) was heated at 50oC for 5 h. The solution was cooled, and solvent removed in vacuo . The residue was dissolved in dioxan (20 ml) at 0oC, a solution of ammonium acetate (2.08g) in water (20 ml) added, and zinc dust (1.76g) added portionwise. The mixture was stirred for 18 h at room temperature, decanted, and diluted with water and extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgSO4) and evaporated in vacuo . The residue was chromatographed on a silica gel column eluted with ethyl acetate:pentane (1:9) to give the title compound as a solid (1.17g, 72%) which recrystallized from 60-80opetrol as needles having m.pt. 141-2oC. 1H n.m.r. (CDCl3) delta 1.32 (s, 3H); 1.38 (s, 3H); 1.45 (s, 9H); 2.70 (dd, J=15, 4, 1H); 3.13 (dd, J=15, 4, 1H); 3.97 (m, 1H); 4.58 (d, J=9, N H); 6.87 (d, J=9, 1H); 7.40 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2-Dimethyl-2H-chromene-6-carbonitrile, its application will become more common.

Reference:
Patent; BEECHAM GROUP PLC; EP375449; (1990); A2;,
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Application of 16588-02-6, 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. 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 17 2-(3,4,5-Trichlorophenoxy)-5-nitrobenzonitrile In a 250 ml single-neck flask equipped with a magnetic stirrer and a reflux condenser fitted with a nitrogen bubbler were placed 8.68 g (0.0475 moles) of 2-chloro-5-nitrobenzonitrile 9.67 g (0.0489 moles) of 3,4,5-trichlorophenol, 6.75 g (0.0489 moles) of anhydrous K2 CO3, and 75 ml of acetonitrile. The mixture was heated to reflux and held there for 3 hrs. The reaction mixture was cooled to room temperature and diluted with 150 ml of water. The product separated as a solid. The solid was filtered off, washed thoroughly with water, and air-dried. The air-dried solid was recrystallized from a mixture of 200 ml of absolute ethanol and 100 ml of acetone to give 11.62 g (71% yield) of purified 2-(3,4,5-trichlorophenoxy)-5-nitrobenzonitrile as small white crystals, mp 162-164 C.

The synthetic route of 2-Chloro-5-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Dow Chemical Company; US4332820; (1982); A;,
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Related Products of 16932-49-3, These common heterocyclic compound, 16932-49-3, name is 2,6-Dimethoxybenzonitrile, 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.

Example 1 Synthesis of 2,6-Dihydroxybenzonitrile (2-Cyanoresorcinol) One potential method utilizes boron tribromide to demethylate 2,6-dimethoxybenzonitrile (1 in ) to generate 2,6-dihydroxybenzonitrile (2). Into a 250 mL 3-neck round bottom flask equipped with stir bar, nitrogen inlet, thermometer, and addition funnel was charged 2,6-dimethoxybenzonitrile (3.99 g, 24.5 mmol) and methylene chloride (27 mL). The solution was cooled to -78 C. by submerging the flask in a dry ice/acetone bath. A solution of boron tribromide (25 g, 99.8 mmol) in methylene chloride (27 mL) was added dropwise via the addition funnel over a period of 1 hour. The temperature was maintained at -78 C. for 2 hours. The mixture was allowed to rise to room temperature. The reaction was then stirred at room temperature overnight and refluxed at 55 C. for 10 hours. Excess boron tribromide was decomposed carefully by the addition of moist methylene chloride. Upon removal of the solvent, the crude product was passed through a column of silica gel using 5% acetone in methylene chloride as eluent to afford 1.42 g (43.0%) of a light brown solid, m.p. 197.5-199.6 C. 1H-NMR (DMSO-d6): 6.39-6.41 (d, 2H, Ar-H), 7.20-7.24 (t, 1H), 10.78 (s, 2H, Ar-O-H).

The synthetic route of 16932-49-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The United States of America, as represented by the Secretary of the Air Force; Tan, Loon-Seng; Wang, David Huabin; US9139696; (2015); B1;,
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Adding a certain compound to certain chemical reactions, such as: 78473-00-4, name is 4-Amino-3,5-dichlorobenzonitrile, 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 78473-00-4, Recommanded Product: 78473-00-4

Into a 1000 mL three-neck flask were put 9.4 g (50 mmol) of 4-amino-3,5-dichlorobenzonitrile, 26 g (253 mmol) of isobutylboronic acid, 54 g (253 mmol) of tripotassium phosphate, 2.0 g (4.8 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-phos), and 500 mL of toluene. The air in the flask was replaced with nitrogen, and this mixture was degassed while being stirred under reduced pressure. After the degassing, 0.88 g (0.96 mmol) of tris(dibenzylideneacetone)palladium(0) was added, and the mixture was stirred at 130 C. under a nitrogen stream for 8 hours to be reacted. Toluene was added to the reacted solution, and the solution was filtered through a filter aid in which Celite, aluminum oxide, and Celite were stacked in this order. The obtained filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography. Toluene was used as a developing solvent. The resulting fraction was concentrated to give 10 g of a yellow oily substance in a yield of 87%. The obtained yellow oily substance was identified as 4-amino-3,5-diisobutylbenzonitrile by nuclear magnetic resonance (NMR) spectroscopy.

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

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; Seo, Satoshi; WATABE, Takeyoshi; MITSUMORI, Satomi; (178 pag.)US2017/92890; (2017); A1;,
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