Month: July 2021

Electric Literature of 5013-77-4,Some common heterocyclic compound, 5013-77-4, name is N-Methyl-2,4-dichlorobenzylamine, molecular formula is C8H9Cl2N, 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: 6.11. 4-Chloro-N-(2,4-dichlorobenzyl)pyrimidin-2-amine (13) and 2-chloro-N-(2,4-dichlorobenzyl)pyrimidin-4-amine (14); 2,4-Dichlorobenzylamine (1.0 mL, 7.4 mmol) was added to a stirring solution of 2,4-dichloropyrimidine (1.0 g, 6.7 mmol) and DIPEA (1.8mL, 10.1mmol) in anhydrous DCE (10mL) and the reaction mixture was stirred at 20C under a nitrogen atmosphere for 24h. LCMS showed the presence of a mixture of regioisomers (System A, RT=1.10min, 63% and 1.25min, 27%). The reaction mixture was diluted with water (50mL) and extracted with DCM (3×50mL). The combined organic extracts were washed with brine (50mL), dried using a hydrophobic frit and evaporated under reduced pressure. The residue was purified by column chromatography on a silica column, using a gradient of 0-100% ethyl acetate-cyclohexane over 40 min. The appropriate fractions were combined and evaporated under reduced pressure to afford the two regioisomers as white solids: less-polar isomer 13 (400 mg, 21%) and the more-polar isomer 14 (950 mg, 49%); 6.23 2-Chloro-N-(2,4-dichlorobenzyl)-N-methylpyrimidin-4-amine (24) Prepared from 12 (0.50 g, 3.4 mmol), N-methyl-(2,4-dichlorobenzyl)amine (0.64 g, 3.4 mmol) and DIPEA (1.3 mL, 7.4 mmol) according to the procedure described for the preparation of 14 to give 24 (0.39 g, 38%) as a white solid: 1H NMR delta (400 MHz, CD3OD) 8.04 (br. s, 1H), 7.52 (d, J = 2.0 Hz, 1H), 7.31 (dd, J = 8.0, 2.0 Hz, 1H), 7.12 (d, J = 8.0 Hz, 1H), 6.66 (br. s, 1H), 4.89 (s, 2H) (obscured by HOCD3), 3.13 (br. s, 3H); LCMS (System A, UV, ES) RT = 1.28 min, [M + H]+ = 302, 304, 306, 100% purity.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-Methyl-2,4-dichlorobenzylamine, its application will become more common.

Reference:
Article; Shukla, Lena; Ajram, Laura A.; Begg, Malcolm; Evans, Brian; Graves, Rebecca H.; Hodgson, Simon T.; Lynn, Sean M.; Miah, Afjal H.; Percy, Jonathan M.; Procopiou, Panayiotis A.; Richards, Stephen A.; Slack, Robert J.; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 14 – 25;,
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Reference of 121-27-7, The chemical industry reduces the impact on the environment during synthesis 121-27-7, name is 5-Chloro-2-(4-chlorophenoxy)aniline, I believe this compound will play a more active role in future production and life.

A solution of 8 (2.56 g, 10.1 mmol), ethyl bromoacetate (7.0 mL, 63 mmol), and N,N-diisopropylethylamine (7.0 mL, 41 mmol) was stirred at 140 C for 5 h. The reaction mixture was cooled down, and diluted with EtOAc (100 mL). The organic layer was washed with 10% aqueous citric acid (100 mL * 2), saturated aqueous NaHCO3, and brine, and dried over MgSO4. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The residue oil was purified by silica gel column chromatography (hexane/EtOAc = 95:5 to 80:20) to afford 9 (3.68 g, 85%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3): delta (ppm) 1.20 (t, J = 7.2, 6H), 4.10 (s, 4H), 4.11 (q, J = 7.2, 4H), 6.76 (d, J = 8.7, 1H), 6.81-6.87 (m, 4H), 7.24 (d, J = 8.7, 2H). 13C NMR (100 MHz, CDCl3): delta (ppm) 14.15, 54.04, 60.95, 118.72, 119.42, 121.65, 122.31, 127.95, 129.56, 129.94, 142.40, 145.35, 155.99, 170.52. LC-MS (ESI) m/z 426, 428 [M+H]+.

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, 5-Chloro-2-(4-chlorophenoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Nakao, Akira; Suzuki, Hiroko; Ueno, Hiroaki; Iwasaki, Hiroshi; Setsuta, Tomofumi; Kashima, Akiko; Sunada, Shinji; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4952 – 4969;,
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Electric Literature of 18282-59-2, A common heterocyclic compound, 18282-59-2, name is 4-Bromo-1,2-dichlorobenzene, molecular formula is C6H3BrCl2, 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.

Tris [(DIBENZYLIDINEACETONE)] di palladium (0) (5 molpercent ; 23 mg) was added to a mixture of 1- [[4- (3-PIPERIDIN-1-YL-PROPOXY)-PHENYL]-PIPERAZINE (D11)] (150 mg; 0.49 [MMOL),] 3, 4-dichloro bromo benzene (160 mg; 1.2 eq), sodium [TERT-BUTOXIDE] (71 mg; 1.1 eq) and racemic 2,2′- bis (diphenylphosphino)-1, 1′-binaphthyl (7.5 molpercent ; 24 mg) in dry [TOLUENE] [(3ML).] The resulting mixture was heated at reflux under argon for 18 hours. The reaction was allowed to cool to room temperature and diluted with ethyl acetate (10 ml). The resulting solids were removed by filtration and the filtrate evaporated in vacuo. The residue was purified by column chromatography on silica eluting with 3percent methanol in [DICHLOROMETHANE] to afford the title compound as a buff solid (45 mg) MS (ES+) [M/E] 448 [M+H] +.

The synthetic route of 18282-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/35556; (2004); A1;,
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Some common heterocyclic compound, 6940-78-9, name is 1-Bromo-4-chlorobutane, molecular formula is C4H8BrCl, 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. Product Details of 6940-78-9

The solution of isobutyronitrile (0.7 g, 10 mmol) in THF (20 mL) was cooled to -80 C and LDA (Lithium diisopropylamide) solution (2.0 M in hexane, 6 mL, 12 mmol) was added over 10 min. The solution was stirred 30 min, and then a solution of 1-bromo-5-chloropentane (1.8 g, 10 mmol) in THF (10 mL) was added over 5 min. After stirring for 90 min, 6 N HCl (6 mL) was added slowly and the temperature allowed to rise to rt. The residue was concentrated under reduced pressure and EtOAc (20 mL) was added. The separated organic layer was washed with water (10 mL). The organic solvent was dried with Na2SO4 and concentrated in vacuo to give the crude product. Purification by column chromatography (petroleum ether (60-90 C)/EtOAc) gave 1.5 g of 2,2-dimethyl-7-chloroheptanenitrile (88%) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 3.57 (t, J = 6.6 Hz, 2H), 1.92-1.72 (m, 2H), 1.58-1.44 (m, 6H), 1.36 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6940-78-9, its application will become more common.

Reference:
Article; Liu, Peng; Xu, Xing; Chen, Lili; Ma, Lei; Shen, Xu; Hu, Lihong; Bioorganic and Medicinal Chemistry; vol. 22; 5; (2014); p. 1596 – 1607;,
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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. 50638-47-6, name is 4-Bromo-2-chloro-1-methoxybenzene, A new synthetic method of this compound is introduced below., Computed Properties of C7H6BrClO

EXAMPLE 21 Preparation of 5-Hydroxy-3-(3-chloro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-cyclopent-2-en-1-one of Formula (67) [0134] A mixture of magnesium turnings (0.31 g, 13.1 mmol), 2-chloro-4-bromoanisole (3.00 g, 13.5 mmol), 4-tert-butyldimethysilyloxy-2-(3,4,5-trimethoxy-phenyl)-cyclopent-2-en-1-one (2.58 g, 6.84 mmol) and dry tetrahydrofuran (35 ml) under nitrogen was stirred at room temperature for 4 h. Reaction was then quenched with dil hydrochloric acid (30 ml), tetrahydrofuran was removed under reduced pressure and the residual reaction mixture was extracted with ethyl acetate (3*35 ml), washed with water (2*20 ml) and dried over sodium sulfate. Concentration and purification by column chromatography over silica gel (eluent-6% acetone in pet ether) afforded the alcohol of the formula (4A) [0135] wherein R1=R5=R6=R7=R10=H, R2=R3=R4=R8=OMe, R9=Cl (1.32 g, 37%). [0136] A solution of the above alcohol of the formula (4A) wherein R1=R5=R6 =R7=R10=H, R2=R3=R4=R8=OMe, R9=Cl wherein (0.95 g, 1.83 mmol) in dry dichloromethane (15 ml) was cooled to 0 C., pyridinium dichromate (1.92 g, 8.17 mmol) was added and the mixture was stirred at room temperature for 3 h. Filtration through celite (3.00 g), washing with dichloromethane (30 ml) and concentration afforded the crude product which was purified by silica gel column chromatography (eluent-3% acetone in pet ether) to yield the title compound of the formula (1B) wherein R=OTBS, R1=R5=R6=R7=R10=H, R2=R3=R4=R8=OMe, R9=Cl (0.32 g, 34%), which on deprotection of TBDMS group using the procedure described in example 10 furnished the compound of formula (67). [0137] Spectral data of compound of the formula of structure (67) [0138] 1H NMR(CDCl3+CCl4): delta 2.96 (dd, J=18 Hz and 2 Hz, 1H), 3.33 (dd, J =18 Hz and 6 Hz, 1H), 3.75 (s, 6H), 3.86 (s, 3H), 3.91 (s, 3H), 4.45-4.54 (m, 1H), 6.42 (s, 2H), 6.81 (d, J=8 Hz, 1H), 7.21-7.29 (m, 1H), 7.48 (bs, 1H). [0139] 13C-NMR (CDCl3+CCl4): delta 37.79, 55.87 (2C), 60.58, 71.57, 106.23 (2c), 111.31, 122.41, 126.82, 127.59, 128.58 (2C), 130.05, 135.90, 138.07, 153.36 (2C), 156.48, 162, 51, 206.95

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; DABUR RESEARCH FOUNDATION; US2003/229146; (2003); A1;,
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Electric Literature of 2687-12-9, A common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, molecular formula is C9H9Cl, 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.

In the reaction (r-1 ‘), a benzene derivative (3A’) (15.2 g, 0.1 mol) and triethyl phosphite represented by the chemical formula (B) (25 g, 0.15 mol ), And the mixture was stirred at 180 C. for 8 hours and then cooled to room temperature. Thereafter, unreacted or remaining triethyl phosphite was distilled off under reduced pressure to obtain a phosphonate derivative (3C ‘) as a white liquid. The yield from the benzene derivative (3A ‘) of the phosphonate derivative (3C’) was 23.5 g (yield: 92 mol%).

The synthetic route of 2687-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyocera Document Solutions Co., Ltd.; Okada, Hideki; Sugai, Akio; Kojima, Kensuke; (52 pag.)JP2017/114808; (2017); A;,
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Electric Literature of 823-57-4, A common heterocyclic compound, 823-57-4, name is 2-Bromo-5-chloroaniline, molecular formula is C6H5BrClN, 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.

The corresponding imidazopyridine (0.2 mmol) was added sequentially to a 25 ml Schlenk tube filled with oxygen and equipped with a magnetic stirrer at room temperature.Cuprous bromide (0.02 mmol), 2-bromo-5-chloroaniline (0.4 mmol),1,10-azaphenanthroline (0.04 mmol), potassium carbonate (0.6 mmol),Carbon disulfide (0.6 mmol) and toluene (2.0 mL) were added by syringe under oxygen.The reaction tube was placed in a 110 C oil bath and stirred for 12 hours.The resulting solution was cooled to room temperature, and 2 mL of deionized water was added to the reaction solution.Mix well, each time with 3mL of ethyl acetate as extractant through liquid separation extraction operation,The crude product is extracted from the reaction solution, and the extract is combined.The solvent was removed by a rotary evaporator; the residue was purified on a silica gel column (silica gel, 200 to 300 mesh, eluent, petroleum ether/ethyl acetate (10:1 v/v)).The target product was obtained in 65.2 mg, yield 83%.

The synthetic route of 823-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Qingdao University of Science and Technology; Yang Daoshan; Yan Qiuli; (17 pag.)CN110294757; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, belongs to chlorides-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 61881-19-4, Product Details of 61881-19-4

To a solution of 28 (0.91 g, 1.7 mmol) in acetone (17 mL) wereadded CF3C(=NPh)Cl (0.53 mL, 3.3 mmol) and K2CO3 (1.1 g,8.3 mmol) at 0 C. After stirring for 2.5 h at the same temperature, thecompletion of the reaction was confirmed by TLC (5:1 n-hexane/EtOAc). The reaction mixture was filtered through Celite pad and thepad was washed with CHCl3. The filtrate and washings were concentrated.The resulting residue was purified by silica gel columnchromatography (25:1 n-hexane/EtOAc) to give 29 (1.2 g, quant.) ascolorless syrup. 1H NMR (500 MHz, CDCl3) delta 7.44-6.70 (m, 17H, Ar),5.08-4.83 (br m, 4H, H-1, H-2, H-3, H-4), 4.15-3.65 (br m, 3H, H-5, H-6a, H-6b), 1.08 (s, 9H, tBu), 1.01 (s, 9H, tBu); 13C NMR (125 MHz,CDCl3) delta 143.5, 143.3, 138.9, 138.6, 135.4, 135.3, 135.3, 135.2, 133.1,133.1, 128.7, 128.4, 128.4, 128.3, 128.2, 128.2, 128.1, 128.1, 128.0,127.9, 127.7, 127.7, 127.7, 126.9, 126.5, 126.2, 126.1, 126.1, 126.0,126.0, 125.6, 124.4, 119.4, 119.2, 84.0, 81.2, 80.0, 77.9, 77.7, 77.5,75.8, 75.5, 75.5, 73.9, 71.0, 68.8, 66.5, 66.2, 27.4, 27.0, 26.9, 22.7,20.0. HRMS (ESI) m/z: found [M+Na]+ 744.2935, C40H46F3NO6Sicalcd for [M+Na]+ 744.2939.

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:
Article; Takato, Koichi; Kurita, Motoki; Yagami, Nahoko; Tanaka, Hide-Nori; Ando, Hiromune; Imamura, Akihiro; Ishida, Hideharu; Carbohydrate Research; vol. 483; (2019);,
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Application of 19752-55-7, 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. 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

A 250 ml round-bottom flask was argonated and consecutively charged with Et2O (60 ml), Mg (1.31 g; 54.0 mmol), I2(one crystal), and a solution of 1-bromo-3,5-dichlorobenzene (12.54 g; 55.5 mmol) in Et2O (60 ml) was added in ca. 5 ml portions over 45 min. Stirring was continued for 3 h at RT, and a solution of 9c (9.52 g; 18.0 mmol) in hot toluene (60 ml, ca. 90 °C) was added slowly, and the mixture was heated to 40 °C for 15 h. A precipitate was decanted, washed with toluene (2 30 ml), treated with concd HClaq. (100 ml) at reflux for 3 h, and cooled to RT. The resulted precipitate was filtered, washedwith concd HClaq. (2 30 ml), and dried. Then, most of the beige solid was dissolved in a hot mixture of water (40 ml), concd HClaq. (120 ml) and ethanol (30 ml), resulted solution was decanted, cooled to RT, and part of the solvent (ca. 50 ml) wasslowly evaporated under reduced pressure. The resulted suspension was filtered, and collected filtrate was washed with concdHClaq. (2 30 ml), and dissolved in CH2Cl2 (150 ml). The organic phase was washed with brine (100 ml), and dried overMgSO4. Then, the mixture was filtered, n-heptane (40 ml) was added, and the mixture was slowly evaporated at 300 mbar (very slow rotations, no heating bath applied). The resulted precipitate was filtered, washed with n-hexane, and dried in vacuo. Filtrate was evaporated and the crystallization procedure was repeated. Both crops were collected and combined to obtain 10c (6.70 g; 9.07 mmol; 50percent calculated as a bromide) as a white solid.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3,5-dichlorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Grudzie?, Krzysztof; Basak, Tymoteusz; Barbasiewicz, Micha?; Wojciechowski, Tomasz M.; Fedory?ski, Micha?; Journal of Fluorine Chemistry; vol. 197; (2017); p. 106 – 110;,
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Adding a certain compound to certain chemical reactions, such as: 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, belongs to chlorides-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 13078-79-0, Quality Control of 2-(3-Chlorophenyl)ethanamine

General procedure: 2.5mmol Thiazole-4-carboxyli acid and 2.0mmol amine were dissolved in 25mL DCM in a dry flask with continuous stirring, followed by the addition of 2.5mmol 3-(3-Dimethylaminopropyl)-1-Ethylcarbodiimide Hydrochloride (2.5mmol). When the temperature of the reaction system cooled to 0C, 50mg 4-dimethylaminopyridine (0.2mmol) was added dropwise and reacted for 1hat 0C. Then the reaction temperature was elevated to room temperature for another 4h. The reaction was stopped by adding 25mL saturated NaHCO3 solution and extracted twice with 20mL dichloromethane (2×20mL). The extracted organic layers were first dried by anhydrous Na2SO4, and then filtered and concentrated under vacuum distillation, obtaining the crude products. Finally, the crude products were further purified using column chromatography (ethy lacetate: petroleum ether, 1:5).

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:
Article; Li, Shengrong; Chen, Siyu; Fan, Jilin; Cao, Zhen; Ouyang, Weihao; Tong, Ning; Hu, Xin; Hu, Jie; Li, Peishan; Feng, Zifeng; Huang, Xi; Li, Yuying; Xie, Mingshan; He, Ruikun; Jian, Jingyi; Wu, Biyuan; Xu, Chen; Wu, Weijian; Guo, Jialiang; Lin, Jing; Sun, Pinghua; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 64 – 73;,
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