Author: tianli

Adding some certain compound to certain chemical reactions, such as: 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, 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 202197-26-0. 202197-26-0

Example-1 Preparation of N1-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-N,N-dimethyl formamidine (8) Into a one liter four necked round bottomed flask, 500 mL of toluene, 50.0 g of 3-chloro-4-(3-fluoro-benzyloxy)-aniline, 50.0 g of dimethylformamide dimethyl acetal and 3.0 mL of acetic acid were charged under stirring. The reaction mixture was maintained at reflux temperature for about 2 hrs and the completion of the reaction was monitored by TLC. The solvent was completely distilled off under vacuum, the resulting syrupy liquid was cooled to room temperature. To this 200 mL of water was added and adjusted to basic pH by adding dilute sodium hydroxide solution. The product was extracted into ethylacetate and separated the organic layer. The organic layer was clarified by carbon treatment and filtered. The filtrate was completely distilled off under vacuum. The mass was cooled to room temperature and added 250 mL of hexane and stirred at 0 to 5 C. for about two hours to crystallize the product. The product was filtered and dried under vacuum at 30-35 C. to get 58.0 gram (95% by theory) of N1-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-N,N-dimethylformamidine as a white crystalline powder. Purity: 99.66% by HPLC Melting-range: 45-47 C. Mass: 307.5 [M+1] IR (KBr, cm-1): 2917, 2798, 2364, 1637, 1591, 1557, 1500, 1453, 1410, 1373, 1269, 1250, 1205, 1137, 1103, 1059, 1016, 926, 877, 859, 809, 772, 749, 704, 680, 637, 606, 519. 1H-NMR (400 MHz; DMSO-D6): delta 2.87 (s, 3H); delta 2.98 (s, 3H); delta 5.15 (s, 2H); delta 6.80-6.83 (dd, 1H); delta 6.99-7.00 (d, 1H); delta 7.04-7.06 (d, 1H); 7.14-7.18 (m, 1H); delta 7.26-7.30 (m, 2H); delta 7.42-7.47 (m, 1H); delta 7.72 (s, 1H) 13C-NMR (400 MHz; DMSO-D6): delta 33.90 (2C), 69.56, 114.0, 115.19, 120.21, 121.51, 121.90, 123.20, 130.45, 140.02, 146.71, 148.41, 153.76, 160.97, and 163.39.

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 3-Chloro-4-((3-fluorobenzyl)oxy)aniline.

Reference:
Patent; Natco Pharma Limited; US2011/263852; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2533-69-9, These common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, 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 the solution containing 4,5-diaminobenzo-15-crown-5 prepared in the last step, methyl 2,2,2-trichloroacetimidate (90 L, 0.70 mmol) was added. The mixture was stirred at rt shielded from light. After 9h, K2CO3 (6.0 g) was added to the mixture. The mixture was stirred for 11 h. The solvent was evaporated to give brown solid. Deionized water (70 mL) was added to the solid, and the mixture was stirred at rt for 5 h. The precipitate was filtered on Celite 545 mu, and washed with deionized water. The precipitate was eluted with a mixture of CHCl3/MeOH (1/1). The solution was concentrated under reduced pressure to give light brown solid, which was passed through a short alumina column chromatography by using a mixture of CHCl3/MeOH (10/1) as an eluent. The fractions were concentrated, and the residue was recrystalized from acetic acid to give 1 (104 mg, 21%) as pale yellow crystal. HRMS (FAB) m/z ([M + Na]+) 637.2486, calcd for C30H38N4O10Na 637.2486. 1H NMR (600 MHz, CDCl3): 7.05 (s, 4H, Ar), 3.96 (br, 8H, crown), 3.86 (br, 8H, crown), 3.75 (br, 16H, crown); 13C NMR (150 MHz, CDCl3): 148.19 (C), 142.92 (C), 133.03 (C), 99.26 (CH), 70.81 (CH2), 70.15 (CH2), 69.22 (CH2), 69.07 (CH2).

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 2533-69-9.

Reference:
Article; Satake, Akiharu; Tanaka, Kazuo; Asakura, Hiroki; Okano, Masahiro; Hashimoto, Tsutsumu; Matsuura, You; Inaba, Yusuke; Oda, Tetsuhisa; Hirota, Shun; Koshino, Hiroyuki; Bulletin of the Chemical Society of Japan; vol. 87; 1; (2014); p. 88 – 97;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2770-11-8, Adding a certain compound to certain chemical reactions, such as: 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, 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 2770-11-8.

General procedure: A mixture of NaOH solution (2 molL-1, 20mL), 1,4-dioxane (2 mL) and compound 4 (5 mmol) was dissolved and cooled to 0 C in an ice bath. While stirring the mixture, compound 14, 15 or 16 was added slowly. Afterwards, the mixture was stirred for another 5h at room temperature. The mixture was then extracted with ethyl acetate, and the solvent was removed in vacuum. The crude product was purified by column chromatography on silica gel to give compounds 17a-17i, 18a-18i or 19a-19i in yields of 30-73%. All the compounds were list in Table1 and the spectral parameters for 1H NMR, IR and MS were as follows.

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-(4-Chlorophenoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wen, Fang; Jin, Hong; Tao, Ke; Hou, Taiping; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 244 – 251;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

33863-76-2, Adding a certain compound to certain chemical reactions, such as: 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, 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 33863-76-2.

Sodium methoxide (4.5M solution in methanol, 2.20 [ML,] 10.0 [MMOL)] was added dropwise to a stirred solution of 1-fluoro-3-chloro-5-bromobenzene (1.00 g, 4.77 [MMOL)] in methanol (28 [ML)] at room temperature under a nitrogen atmosphere. The mixture was heated at reflux for 3 days and then cooled to room temperature. The mixture was evaporated under reduced pressure and the resulting yellow oil was dissolved in [DICHLOROMETHANE] (30 [ML).] The [DICHLOROMETHANE] solution was washed with water [(2X20] [ML)] dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue was purified by chromatography on silica gel eluting with cyclohexane to provide the title compound as a colourless oil (302 mg). [1 H-NMR (400MHZ, CDC13)] : [8] 3.77 (s, 3H), 6.82 (s, 1 H), 6.94 (s, 1 H), 7.09 (s, [1 H).] Microanalysis : Found: C, 37.94 ; H, 2.75. [C7H6BRCIO] requires ; C, 37.96 ; H, 2.73%.

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, 1-Bromo-3-chloro-5-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/29051; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1996-29-8, Name is 1-Bromo-4-chloro-2-fluorobenzene, 1996-29-8, belongs to chlorides-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.

Step-l: Synthesis of 3-bromo-6-chloro-2-fluorobenzaldehyde 2Reaction scheme: To a stirred solution of l-Bromo-4-chloro-2-fluorobenzene (200 g, 0.955 mol, 1.0 equiv.) in anhydrous THF (2.0 L) was added 2.0 M lithium diisopropylamide (LDA) in THF (620 mL, 1.24 mol, 1.3 equiv.) at -50 C, the reaction mixture was allowed to -20 C and stirred for 1 h. Then it was re-cooled to -50 C and slowly added DMF (184.8 mL,2.48 mol, 2.6 equiv.) at the same temperature. The mixture was allowed to 0 C and stirred for 30-45 min. After completion of the reaction (monitored by TLC), it was quenched with the slow addition of ice cold water (2.0 L); then diluted with ethyl acetate (2.0 L) and stirred for 15 min at room temperature. The organic layer was separated and aqueous layer was extracted with ethyl acetate (2 x 1.0 L). The combined organic layers were washed with water (2 x 1.0 L); 1.0 N HC1 (1.0 L) and.5% NaCl solution (2.0 L). The organic layer was dried over anhydrous NaiSOr. concentrated under vacuum. The resultant crude solid was directly used for next step without further purification. Yield: 210.0 g, 93% (reported 78%). NMR (400 MHz, CDCb): d 10.39 (d, J= 0.8 Hz, 1H), 7.69 (dd, Ji = 7.2 Hz, J2 = 8.8 Hz, 1H), 7.19 (dd, Ji = 1.2 Hz, J2 = 8.4 Hz, 1H).

Statistics shows that 1-Bromo-4-chloro-2-fluorobenzene is playing an increasingly important role. we look forward to future research findings about 1996-29-8.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BENDER, John A.; FRENNESSON, David B.; GILLIS, Eric P; IWUAGWU, Christiana; KADOW, John F; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M.; RAJAMANI, Ramkumar; SAULNIER, Mark G.; WANG, Alan Xiangdong; (313 pag.)WO2019/198024; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

27139-97-5, name is 2-Bromo-4-chloro-1-methylbenzene, belongs to chlorides-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. 27139-97-5

To a solution of 2-bromo-4-chloro-l-methylbenzene (25 g, 0.123 mol) in anhydrous THF (150 mL) at -78 0C under N2 was added drop wise a solution of n- BuLi (2.5 M, 49 mL, 1.18 mol). After stirring at -78 0C for 1 h, a solution of tert- butyl 3-(5-chloro-2-methylphenyl)-3-oxopropyl(methyl)carbamate (26 g, 0.104 mol) in anhydrous THF (150 mL) was added drop wise. After addition, the reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was quenched with saturated NH4Cl, extracted three times with ethyl acetate, and dried over Na2SO4. Solvent removal and flash column chromatography afford tert-butyl 3-(5-chloro-2-methylphenyl)-3-oxopropyl(methyl)carbamate (3.3 g, yield 9 percent). 1H NMR (CDCl3, 400 MH2) delta 1.44 (s, 9H), 2.45 (s, 3H), 2.90 (s, 3H), 3.10 (m, 2H), 3.60 (m, 2H), 7.10 (m, 3H).

Statistics shows that 27139-97-5 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-4-chloro-1-methylbenzene.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; WO2008/156816; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

41965-95-1, 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. 41965-95-1, name is 3-Chloro-4-methoxybenzylamine Hydrochloride, A new synthetic method of this compound is introduced below.

2-acetyl-10-[(3-chloro-4-methoxybenzyl)amino]-l,2,3,4- tetrahydrobenzo[b][l,6]naphthyridine-8-carbonitrile, H [00206] A mixture of 26 (0.14 mmol), 3-chloro-4-methoxybenzyl amine hydrochloride (0.70 mmol), TEA (0.70 mmol) and Nal (0.007 mmol) in NMP (2 mL) was heated to 130 C and stirred overnight. The mixture was diluted with CH2C12 (10 mL) and washed with H20 (2×10 mL) and brine (10 mL). The organic layers were dried over Na2S04, filtered and evaporated under reduced pressure. Flash Chromatography (AcOEt: MeOH 9: 1) gave the desired product (20%> yield). MS ESI (m/z) 421 (M+H)+; 1H NMR (300 MHz, CDC13) delta 8.34 (s, IH), 7.96 (d, IH, J=8.7 Hz), 7.73 (dd, lH, Ji=1.5, J2=9.0 Hz), 7.31 (d, 1H, J=2.1 Hz), 7.20 (dd, IH, Ji=2.1, J2=8.4 Hz) , 6.93 (d, IH, J=8.1 Hz), 4.70 (s, 2H), 4.64 (d, 2H, J=6.0 Hz), 4.42 (s, IH), 3.91 (s, 3H), 3.82 (t, 2H, J=6.0 Hz), 3.20 (t, 2H, J=6.0 Hz), 2.21 (s, 3H).

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; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; LANDRY, Donald, W.; DENG, Shixian; FIORITO, Jole; ARANCIO, Ottavio; WASMUTH, Andrew; WO2015/9930; (2015); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, 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. 2770-11-8

General procedure: A mixture of NaOH solution (2 molL-1, 20mL), 1,4-dioxane (2 mL) and compound 4 (5 mmol) was dissolved and cooled to 0 C in an ice bath. While stirring the mixture, compound 14, 15 or 16 was added slowly. Afterwards, the mixture was stirred for another 5h at room temperature. The mixture was then extracted with ethyl acetate, and the solvent was removed in vacuum. The crude product was purified by column chromatography on silica gel to give compounds 17a-17i, 18a-18i or 19a-19i in yields of 30-73%. All the compounds were list in Table1 and the spectral parameters for 1H NMR, IR and MS were as follows.

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 2770-11-8.

Reference:
Article; Wen, Fang; Jin, Hong; Tao, Ke; Hou, Taiping; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 244 – 251;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 6579-54-0 as follows. 6579-54-0

(a) Step 1 [0256] A solution of 1H-indole-3-carboxaldehyde (0.290 g, 2.00 mmol) in methylene chloride (4 mL) was added with 2,6-dichlorophenylsulfonyl chloride (0.589 g, 2.40 mmol) and diisopropylethylamine (0.310 g, 2.40 mmol), and the mixture was stirred overnight at room temperature. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate to terminate the reaction, and then extracted three times with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain 1-(2,6-dichlorophenylsulfonyl)-1H-indole-3-carboxaldehyde (0.658 g, 93%).1H NMR (300 MHz, CDCl3) delta 7.32-7.38 (m, 2H), 7.41-7.45 (m, 1H), 7.48-7.51 (m, 2H), 7.63-7.67 (m, 1H), 8.28-8.31 (m, 1H), 8.41 (s, 1H), 10.18 (s, 1H).

According to the analysis of related databases, 6579-54-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The University of Tokyo; Riken; NAGANO Tetsuo; OKABE Takayoshi; KOJIMA Hirotatsu; SAITO Nae; NAKANO Hirofumi; ABE Masanao; TANAKA Akiko; HONMA Teruki; YOKOYAMA Shigeyuki; TSUGANEZAWA Keiko; YUKI Hitomi; EP2565192; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, molecular formula is C8H17Cl2N, 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. 26487-67-2.

General procedure: A mixture of riccardin D, alkyl chloride hydrochloride and potassium carbonate in acetone was stirred under reflux for 24h. The insoluble material was then filtered off and the filtrate was concentrated to provide the residue that was purified by flash column chromatography, eluting with a gradient mixture of MeOH/ EtOAc/aqueous ammonia (93:5:2 to 80:18:2, V/V), to yield the pure product (compounds 17a-17f and 18a-18f) as a solid in good yield.

The synthetic route of 1-(2-Chloroethyl)azepane hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sun, Bin; Liu, Jun; Gao, Yun; Zheng, Hong-bo; Li, Lin; Hu, Qing-wen; Yuan, Hui-qing; Lou, Hong-xiang; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 603 – 618;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics