Tag: M.W=100-200

5653-62-3, A common heterocyclic compound, 5653-62-3, name is 2,3-Dimethoxybenzonitrile, molecular formula is C9H9NO2, 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 stirred solution of 2,3-dimethoxybenzonitrile (25)(5.0 g, 30 mmol) in Et2O (12.5 mL) under N2 atmosphere was added methylmagnesium bromide (37% in Et2O) (12.5 mL, 37 mmol). The mixture was stirred for 16 h, and then 50% AcOH (20 mL) was added. After it was stirred for 30 min, the solution was poured into crushed ice, extracted with CH2Cl2, washed with 10% Na2CO3 and then with water, dried over MgSO4 and concentrated. The crude was purified by column chromatography (SiO2, n-hexane: EtOAc=4:1) to give 26. Liquid; yield: 92.5%; 1H-NMR (CDCl3, 200 MHz): delta 2.56 (s, 3H), 3.82 (s, 3H), 3.85 (s, 3H), 6.99-7.02 (m, 2H), 7.13-7.18 (m, 1H); 13C-NMR (CDCl3, 50 MHz): delta 31.18, 55.98, 61.29, 115.83, 120.80, 123.94, 133.62, 148.63, 153.04, 200.26; Anal. calcd for C10H12O3: C, 66.65; H, 6.71. Found: C, 66.60; H, 6.73.

The synthetic route of 5653-62-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Efficient Pharma Management Corporate; US2012/15908; (2012); A1;,
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1885-38-7, 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. 1885-38-7, name is (E)-Cinnamonitrile, A new synthetic method of this compound is introduced below.

General procedure: Under a nitrogen atmosphere, a mixture of [RhCl(C2H4)2]2 (1.8 mg,0.0045 mmol) and ligand L1f (3.7 mg, 0.0099 mmol) in toluene(1 mL) was stirred at r.t. for 15 min, at which time arylboronic acid(0.60 mmol) was added, followed by cyanoalkenes (0.30 mmol),aqueous KOH (0.75 M in H2O, 0.20 mL, 0.15 mmol) and toluene(1 mL). The reaction was stirred at 80 C for 12 h, after which thereaction mixture was concentrated in vacuo and purified by silica gelflash column chromatography (petroleum ether/ethyl acetate as eluent)to give the product

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; Xue, Feng; Zhu, Yong; Qi, Xiaolei; Journal of Chemical Research; vol. 42; 6; (2018); p. 300 – 304;,
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16588-02-6, The chemical industry reduces the impact on the environment during synthesis 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, I believe this compound will play a more active role in future production and life.

In order to prepare a reaction mixture, a diselenide compound represented by a general formula R?-CH2—-a solvent, and a reducing agent were prepared. As the diselenide compound represented by the general formula R??-CH2-Se-Se–CH2—R? of the reaction mixture, various substances such as (SeCH2COOEt)2? (p-NO2PhCH2Se)2, (p-CNPhCH2Se)2, and the like were used. The diselenide compounds were as shown in [Table 1]. About 0.6 eq. of the diselenide compound was used. As the solvent, anhydrous dimethylformaldehyde (DMF) was used. Further, as the reducing agent, about 0.6 eq. of dithiothreitol (DTT) was used.10291] To be specific, the reaction mixture was prepared by adding the diselenide compound represented by the general formula R?CH2Se-Se-CH2—-R? and the reducing agent to 2 mL of the solvent. The reaction mixture was stirred for 1 hour at a constant temperature of 60 C.10292] After the reaction mixture was prepared, an aromatic compound as a starting material for producing the selenophene-fused aromatic compound was added to the reaction mixture at a time. Then, the reaction mixture was stirred for 30 minutes at a constant temperature of 60 C.10293] As the base to be added afier the starting material is added to the reaction mixture with stirring, a weak base K2C03 was used. 2.5 eq. of the base was added to the reaction mixture at room temperature with stirring for 24 hours at a constant temperature of 60 C.10294] After the base was added and the stirring was finished, it was observed that the starting material was completely consumed by using a thin layer chromatography in a mixture of ethyl acetate:hexane (EA:Hex). The solvent contained in the reaction mixture was removed in a vacuum, and a crude solid was extracted 3 times by using about 25 mE of a solvent including dichloromethane:water (1:1). An organic phase collected through the extraction process was dried in an anhydrous environment by using MgSO4, and the solvent was evaporated in a vacuum. The residue was refined by column chromatography using a silica gel column. A pure product, i.e. the selenophene-fused aromatic compound produced in the present Example, was eluted by using ethyl acetate and hexane, and recrystallized by using methanol and then filtered.

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-5-nitrobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Samsung Life Public Welfare Foundation; Industry-Academia Cooperation Group of Sejong University; Lim, Dongyeol; Nam, Do-Hyun; Dubey, Rashmi; Lee, Hangeun; US2014/213790; (2014); A1;,
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143879-80-5, 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. 143879-80-5, name is 2,3,4-Trifluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2,3,4-trifluorobenzonitrile (3 g, 19 mmol), tert-butyl carbazate (4 g, 30 mmol) and Hunig’s base were dissolved in dioxane (10 mL) and heated at 100 C. for 3 d. The mixture was concentrated and then partitioned between toluene (25 mL) and water (29 mL). The toluene layer was added to a column and chromatographed (silica gel, 10 to 40% ethyl acetate in hexanes) to give product as an oil. Recrystallization from ethyl acetate/hexanes gave N’-(4-cyano-2,3-difluoro-phenyl)-hydrazinecarboxylic acid tert-butyl ester (1.16 g, 22%) as a white powder. A second crop (0.5 g, 10%) was obtained as a slightly pinkish powder. LCMS (m/z): M+H=170.1 (loss of BOC).

The synthetic route of 2,3,4-Trifluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huang, Kenneth He; Ommen, Andy J.; Barta, Thomas E.; Hughes, Philip F.; Veal, James; Ma, Wei; Smith, Emilie D.; Woodward, Angela R.; McCall, W. Stephen; US2008/269193; (2008); A1;,
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6393-40-4, 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 6393-40-4 as follows.

A sample of 2 (6.13 mmol) was suspended in 55 mL ofdry methanol and the suspension was saturated with HCl(g)for 30 min. After 4 days stirring at room temperature, thesuspension was filtrated and the solid was washed with120 mL of ethyl ether. The yellow solid obtained wasdissolved in dry methanol and saturated with NH3 during6 h. The solution was concentrated to half and to theresulting solution was added 60 mL of ethyl ether. Theresulting precipitated was collected by filtration and washedwith 50 mL of ethyl acetate, affording the interest product. 4-Amino-3-nitrobenzamidine hydrochloride (3) This product was obtained as a yellow solid (60%yield); mp > 300 C; IR (ATR) nu / cm-1 3453, 3420 (NH2),3134, 3052 (NH.HCl amidine), 1685 (C=N), 1628 (NH2);1H NMR (200 MHz, DMSO-d6) delta 9.38 (br s, 2H, Hamidine), 9.12 (br s, 2H, H amidine), 8.62 (s, 1H, H arom.),8.17 (s, 2H, NH2), 7.87 (d, J 9.0 Hz, 1H, H arom.), 7.19 (d,J 9.0 Hz, 1H, H arom.); 13C NMR (50 MHz, DMSO-d6) delta 163.5, 149.1, 133.6, 129.6, 127.6, 119.4, 113.2.

According to the analysis of related databases, 6393-40-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; de Souza, Thiago B.; Oliver, Josidel C.; Gomes, Ana Paula B.; Aragao, Cicero Flavio S.; Ferreira, Leandro S.; Nogueira, Fernando Henrique A.; Dias, Amanda Latercia T.; Alves, Ricardo J.; Journal of the Brazilian Chemical Society; vol. 29; 6; (2018); p. 1304 – 1317;,
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A common heterocyclic compound, 134227-45-5, name is 3,4,5-Trifluorobenzonitrile, molecular formula is C7H2F3N, 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. 134227-45-5.

To N, N- dimethylformamide (10mL) solution of 3,4,5-trifluorobenzonitrile (305mg), phenol (213mg), cesium carbonate (760mg) were added,and the mixture was stirred for 3 h at 80 . Aftercooling the reaction mixture to room temperature, water was added, and themixture was extracted with ethyl acetate. The combined organic layerswere washed with saturated brine, dried over anhydrous magnesium sulfate, andconcentrated under reduced pressure. The resulting residue was purified bysilica gel column chromatography (eluent: ethyl acetate / heptane = 1/10), toobtain the desired product (387mg).

The synthetic route of 3,4,5-Trifluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISHIHARA SANGYO KAISHA LIMITED; TSUKUDA, SHINTARO; IWAMOTO, TAKUYA; MORIYAMA, TAICHI; (45 pag.)JP2016/56117; (2016); A;,
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Adding some certain compound to certain chemical reactions, such as: 40497-11-8, name is Ethyl 2,3-dicyanopropanoate, 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 40497-11-8. 40497-11-8

Ethyl 2,3-dicyanopropionate (1.0 mmol) was added to 20.0 ml of ethanol, vigorously stirred., then Hydrazine hydrate (2.0 mmol) was added to the reaction solution, and the mixture was heated under reflux for 3 hours. The heating was stopped and the mixture was cooled to room temperature. The mixture was concentrated in vacuo and the mixture was extracted with ethyl acetate and water. The resulting ethyl acetatewas extracted andconcentrated in vacuo to give 5-amino-1H-pyrazole-3-cyano as a white solid. The intermediate was used directly in the next step without further purification.

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 Ethyl 2,3-dicyanopropanoate.

Reference:
Patent; South China Agricultural University; Xu Hanhong; Jiang Xunyuan; Wei Xiaoyi; Zhang Zhixiang; Lin Fei; Yao Guangkai; Deng Chengju; (50 pag.)CN108003162; (2018); A;,
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1080-74-6, Name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, 1080-74-6, 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.

Compound 4 (0.15 g, 0.1275 mmol) and 2-(3-oxo-2,3-dihydroinden-1-ylidene)malononitrile (0.371 g, 3.825 mmol) were dissolved inchloroform (15 mL). A drop of pyridine was added and the solution wasleft to stir at 65 C overnight. The reaction was dissolved in ethanol andstirred for another 10 min. The product was extracted with dichloromethaneand dried over MgSO4. After removal of the solvent, thecrude product was chromatographically purified on silica gel column(eluted with chlorobenzene) to afford dark purple solid (105 mg, 85%).1H NMR (500 MHz, CDCl3) delta: 8.95 (s, 3H), 8.75 (m, 3H), 8.50 (m, 3H),8.01 (m, 3H), 7.98 (m, 6H), 7.91 (s, 3H), 7.83 (m, 6H), 7.69 (d, 3H),3.04 (m, 6H), 2.28 (m, 6H), 0.95 (m, 36H), 0.62 (m, 30H). 13C NMR (125 MHz, CDCl3) delta: 187.44, 159.75, 159.54, 153.77, 145.88, 145.39,141.05, 139.05, 137.13, 136.97, 135.96, 135.41, 134.29, 133.62,130.51, 124.42, 124.40, 124.27, 123.99, 122.85, 121.62, 119.14,113.53, 113.46, 70.06, 56.40, 37.23, 31.63, 29.57, 24.22, 22.41, 14.02.MS (MALDI-TOF) calculated for C114H108N6O3S3, 1705.77; found,1705.94.

Statistics shows that 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile is playing an increasingly important role. we look forward to future research findings about 1080-74-6.

Reference:
Article; Lin, Kaiwen; Xie, Boming; Wang, Zhenfeng; Xie, Ruihao; Huang, Yunping; Duan, Chunhui; Huang, Fei; Cao, Yong; Organic electronics; vol. 52; (2018); p. 42 – 50;,
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The chemical industry reduces the impact on the environment during synthesis 42872-74-2, name is 3-Bromo-4-methylbenzonitrile, I believe this compound will play a more active role in future production and life. 42872-74-2

General procedure: To 2-bromo-3-methylbenzoic acid (21, 159 g, 739 mmol) in dichloromethane (1000 mL) was added triethylamine (TEA, 119.7 mL, 813 mmol, 1.1 equiv) followed by iso-butyl chloroformate (101.5 mL, 813 mmol, 1.1 equiv) in dichloromethane (DCM, 200 mL) at 0 C over 10 min. Concentrated ammonia water (323 mL) was then added at 0 C over 2 min. The reaction mixture was poured into water (200 mL), cooled to rt and filtered. The solid was washed with water (2 ¡Á 300 mL), 0.5 N HCl (2 ¡Á 150 mL) and dried to give the amide as a solid (120 g, yield 76%). To the solution of the amide obtained (50 g, 233.6 mmol) in DMF (300 mL) was added 2,4,6-trichloro-1,3,5-triazine (64.6 g, 350.4 mmol, 1.5 equiv) dropwise at 0 C and the reaction was stirred at rt overnight. To the reaction was added 600 mL of water and the reaction was stirred for 30 min. All insoluble was removed by filtration and the solid was triturated with ethyl acetate (EA, 3 ¡Á 100 mL) for 40 min and filtered. The filtrate was washed with saturated sodium carbonate (3 ¡Á 200 mL), saturated sodium chloride (200 mL) and dried over anhydrous sodium sulfate.The solvent was removed under reduced pressure to give 22 as a solid (42 g, yield 87.3%). To a solution of 22 (20 g, 102.2 mmol, 1 equiv) in CCl4 (200 mL) was added NBS (18.2 g, 102.0 mmol, 1.0 equiv), Bz2O2 (0.15 g, 0.6 mmol, 0.006 equiv). The reaction was refluxed overnight under N2, cooled and filtered. The filtrate was crystallized at 0 C to provide the brominated intermediate (15 g, yield 53.6%). To a solution of the brominated intermediate (90 g, 327.3 mmol) in DMF (760 ml) was added KOAc (38.6 g, 393.1 mmol, 1.2 equiv). The reaction mixture was stirred at 80 C for 1 h, cooled and water (1 L) was added. The mixture was extracted with EA (1 L). The organic layer was washed with 0.5 N HCl (3 ¡Á200 mL), 2% NaHCO3 (200 mL) and dried over anhydrous sodium sulfate. The solvent was removed to give 23 as a yellow solid (77.3 g, yield 92.9%). 1H NMR of 23 (500 MHz, CDCl3): delta 2.16 (s, 3H), 5.21 (s, 2H), 7.43-7.46 (t, 1H,), 7.63 (m, 2H) ppm. To a solution of 23 (20 g, 78.8 mmol) in 1,4-dioxane (400 mL) was added bis(pinacolato)diboron (30 g, 118.1 mmol, 1.5 equiv) and KOAc (33.2 g, 338.1 mmol, 4.3 equiv). After being de-gassed and backfilled with nitrogen, Pd(dppf)Cl2 (3.2 g, 3.935 mmol, 0.05 equiv) was added. The reaction was refluxed overnight under nitrogen, cooled and filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography eluted with petroleum ether (PE)/EA = 5:1 to give 24 as red oil (29 g, crude yield 100% with 80% purity). 1H NMR of 24 (500 MHz, DMSO-d6): delta 1.42 (s, 12H), 2.20 (s, 3H), 5.25 (s, 2H), 7.44-7.49 (t, 1H), 7.57-7.64 (m, 2H) ppm. To a solution of 24 (29 g) in MeOH (100 mL) was added a solution of NaOH in MeOH (7.0 g/130 mL, 175.8 mmol, 2.3 equiv) and the reaction was stirred for 2 h at rt. The reaction mixture was concentrated under vacuum and the residue was dissolved in THF (150 mL) and 2 N HCl (138 mL, 69 mmol, 0.9 equiv). The reaction was stirred at rt for 50 min, concentrated and filtered. The solid was washed with water (3 ¡Á 20 mL) and petroleum ether (3 ¡Á 20 mL) to provide 25 (7.6 g, yield 62%). 1H NMR of 25 (500 MHz, DMSO-d6): delta 5.05 (s, 2H), 7.63-7.68 (t, 1H), 7.73-7.81 (m, 2H) ppm. To Raney Ni (0.849 g, 14.5 mmol, 2.3 equiv) in formic acid (10 mL) and water (2 mL) was added 25 (1 g, 6.29 mmol) at rt. The reaction was stirred at 100 C for 1 h, cooled and then filtered. The solvent was removed to give a solid that was purified by silica gel column chromatography eluted with CH2Cl2 to give 26 as a solid (0.714 g, yield 70%). 1H NMR of 26 (500 MHz, CDCl3): delta 10.03 (s, 1H), 8.08 (s, 1H), 7.86 (t, 1H), 7.63-7.71 (m, 2H), 5.20 (s, 2H) ppm. To a mixture of HCOOH (116.2 g, 10.0 equiv) and TEA (102.2 g, 4.0 equiv) were added 26 (40.9 g, 252.5 mmol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (43.7 g, 1.2 equiv). The resulting mixture was refluxed for 15 h and cooled to rt. Hydrochloric acid (2 N, 320 mL) was added into the mixture that was then extracted with ethyl acetate twice (2 ¡Á 250 mL). The combined organic layer was washed with 2 N HCl (160 mL) and rotary evaporated to give the crude product that was recrystallized from DMF and 2 N HCl (34:204 mL) providing compound 1 as a white solid (15.6 g, yield 30%). An additional recrystallization from DMF and 2 N HCl (16:96 mL) was performed to give high purity product (12.9 g).

The chemical industry reduces the impact on the environment during synthesis 42872-74-2. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Yong-Kang; Plattner, Jacob J.; Freund, Yvonne R.; Easom, Eric E.; Zhou, Yasheen; Gut, Jiri; Rosenthal, Philip J.; Waterson, David; Gamo, Francisco-Javier; Angulo-Barturen, Inigo; Ge, Min; Li, Zhiya; Li, Lingchao; Jian, Yong; Cui, Han; Wang, Hailong; Yang, Jian; Bioorganic and Medicinal Chemistry Letters; vol. 21; 2; (2011); p. 644 – 651;,
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622-75-3, 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. 622-75-3, name is 2,2′-(1,4-Phenylene)diacetonitrile, A new synthetic method of this compound is introduced below.

Add 4- (2-oxiranylmethoxy) benzaldehyde (0.01 mol, 1.78 g), terephthalonitrile (0.0045 mol, 0.7000 g), and 150 mL of ethanol to a 250-mL single-necked bottle, and stir for 10 minutes. After several minutes, solid potassium hydroxide (0.03 mol, 1.68 g) was added, and after 4 to 6 hours of reaction, the reaction was stopped.After the temperature of the reaction system was cooled to room temperature, the solid product was collected by suction filtration, washed with water and dried to obtain a crude product. The crude product was recrystallized from a mixed solvent of DMF and ethanol (V: V = 3: 1) to obtain a pure yellow product 1.95. g, yield 93%.

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; Xiangtan University; Zhang Hailiang; Tan Huiping; Yuan Yongjie; Yang Bohao; (15 pag.)CN110407772; (2019); A;,
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