Author: Jessica.F

7149-75-9, name is 4-Chloro-3-methylaniline, 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. name: 4-Chloro-3-methylaniline

Step 1 (0443) To a mixture of 3-iodo-4-methylbenzaldehyde (600 mg), 4-chloro-3-methylphenylamine (414 mg), tetrahydrofuran (2 mL) and methanol (6 mL) was added decaborane (90 mg), and the mixture was stirred at room temperature for 1 hour. After the mixture was diluted with ethyl acetate, to the resulting mixture was added aminopropyl silica gel powder (3 g). The resulting mixture was filtered and the filtrate was concentrated under reduced pressure to give (4-chloro-3-methylphenyl)-(3-iodo-4-methylbenzyl)amine (900 mg).

The synthetic route of 7149-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; Inoue, Hitoshi; Ohno, Kohsuke; Nakamura, Tetsuya; Ohsawa, Yusuke; (58 pag.)US2016/362368; (2016); A1;,
Chloride – Wikipedia,
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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. 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H17Cl2N

General procedure: Commercially available 5-chloro benzoxazoles or benzothiazoles(5 mmol) and K2CO3 (15 mmol) were added to 50 mL of DMF.The mixture was heated at 60 C and 1-(2-chloroethyl)hexahydro-1H-azepine hydrochloride (6.5 mmol) was added. The mixture was maintained at 60 C under stirring for 3 h, then was cooled to room temperature, poured into water, and extracted with diethyl ether(3 50 mL). The organic layer was washed with brine, dried overan hydrous Na2SO4 and evaporated under reduced pressure to give are sidue, which was purified by flash column chromatography oversilica gel using ethyl acetate/methanol 8:2 v/v as eluent. Immediately after solvent evaporation, free bases were converted into hydrochlorides by dissolving the corresponding amine in diethyl ether and treating with a 1.25MHCl ethanol solution (pH 1e2). The precipitate was filtered off, washed with diethyl ether, and dried under nitrogen. The following compounds were obtained using this procedure:

The synthetic route of 26487-67-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Romeo, Giuseppe; Prezzavento, Orazio; Intagliata, Sebastiano; Pittala, Valeria; Modica, Maria N.; Marrazzo, Agostino; Turnaturi, Rita; Parenti, Carmela; Chiechio, Santina; Arena, Emanuela; Campisi, Agata; Sposito, Giovanni; Salerno, Loredana; European Journal of Medicinal Chemistry; vol. 174; (2019); p. 226 – 235;,
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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. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, A new synthetic method of this compound is introduced below., Computed Properties of C6H3BrClF

Example 9: 4- [3- (5-Chloro-2-fluoro-phenyl)-prop-2-ynyl]-piperazine-1- carboxylic acid ethyl ester; 4-Prop-2-ynyl-piperazine-1-carboxylic acid ethyl ester (0.22 g, 0.96 mmol), 2-bromo- 1-chloro-1-fluorobenzene (0.14 mL, 1.2 mmol) and diisopropylamine (0.17 mL, 1.2 mmol) were dissolved in dioxane (1 mL), and the solution degassed with argon for -10 minutes. Bis (methylcyanate) palladium (II) chloride (12 mg, 0.05 mmol), copper iodide (4 mg, 0.02 mmol) and tri-tert-butylphosphine (0.014 mL, 0.06 mmol) were added, and the reaction was sealed and allowed to stir for 16 h. Reaction mixture was diluted with EtOAc (5 mL) and filtered over celite using EtOAc. The organic layer was washed with NH4C1 solution (4 x 10 mL), then dried (Na2S04), filtered and concentrated onto silica gel. Chromatography (SPE) eluting with 30-50 % EtOAc/ hexanes afforded 113 mg (36 %) of the title compound as a yellow oil. 1H NMR (CDC13) 8 (ppm): 7.41 (dd, 1H), 7.26 (ddd, 1H), 7.02 (t, 1H), 4.16 (q, 2H), 3.60 (s, 2 H), 3.56 (t, 4H), 2.61 (t, 4H), 1.28 (t, 3H).

The synthetic route of 1996-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB?; NPS PHARMACEUTICALS, INC.; WO2005/80363; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 61881-19-4

To 10 (3.0 g, 1.5 mmol) and N-phenyl trifluoroacetimidoyl chloride (0.95 g, 4.59 mmol, 3.0 eq) in acetone (57.5 ml) was added K2CO3 (0.6 g, 4.59 mmol, 3.0 eq), and the mixture was stirred at room temperature for 1 h. The mixture was filtered, concentrated, and purified by silica gel column chromatography (hexane : ethyl acetate = 2:1) to obtain the 11 (3.2 g, 97%) as a white solid. m.p. 149 – 151 oC. [a]25D = – 218.6 (c = 1.00 in CHCl3). 1H NMR (400 MHz, CDCl3) delta 8.57 – 6.52 (m, 65H), 6.25 (d, J = 10.5 Hz, 1H), 6.12 – 6.03 (m, 2H), 5.97 (d, J = 2.9 Hz, 1H), 5.89 – 5.68 (m, 4H), 5.59 (dd, J = 10.5, 3.2 Hz, 1H), 5.17 (d, J = 9.1 Hz, 1H), 4.61 (dd, J = 12.4, 6.2 Hz, 2H), 4.48 (d, J = 12.9 Hz, 1H), 4.35 (d, J = 12.3 Hz, 1H), 4.31 – 4.01 (m, 8H), 3.93 (d, J = 9.6 Hz, 1H), 3.88 – 3.65 (m, 5H), 1.64 (s, 3H).13C NMR (100 MHz, CDCl3) delta 171.1-164.7 (C, C=O), 143.1 (C, N-C), 141.0 133.9-128.0 (C, Ar), 124.9 (C, C-F), 119.2, 116.2q, CF3, 106.3, 100.7, 100.6, 98.8, 70.5, 70.2, 69.9, 69.8, 69.5, 69.1, 68.5, 67.4, 67.2, 66.9, 63.8, 63.3, 62.6, 61.5, 60.4, 60.1, 59.2, 58.8, 20.0.ESI-MS (m/z): [M+Na]+ : calcd for C118H96F3NO34Na+ 2150.5658, found 2150.5673.

According to the analysis of related databases, 61881-19-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Hongliang; Wang, Hengtao; Xu, Qiulong; Lu, Rui; Cao, Yunhua; Wang, Zhefeng; Tang, Pingping; Lin, Feng; Li, Yingxia; Carbohydrate Research; vol. 448; (2017); p. 6 – 9;,
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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. 4152-90-3, name is (3-Chlorophenyl)methanamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of (3-Chlorophenyl)methanamine

STEP7 Preparation of N-(3-chlorobenzyl)-3-((3aR,4S,6aS)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)imidazo[1,2-a]pyrazin-8-amine A mixture of 8-chloro-3-((3aR,4S,6aS)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)imidazo[1,2-a]pyrazine (500 mg, 1.60 mmol), (3-chlorophenyl)methanamine (0.236 mL, 1.92 mmol) and DIPEA (0.700 mL, 4.01 mmol) in i-BuOH (8.0 mL) was subjected to microwave irradiation at 170° C. for 4 h. (The reaction was repeated 4 times in same scale). The combined reaction mixture was cooled to room temperature, diluted with EtOAc and washed with water and brine. The separated organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on NH-SiO2 (Hexanes:EtOAc=1:1) to give N-(3-chlorobenzyl)-3-((3aR,4S,6aS)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)imidazo[1,2-a]pyrazin-8-amine (2.40 g, 90percent) as a yellow oil. 1H-NMR (CDCl3, 400 MHz): delta 7.44 (d, J=4.8 Hz, 1H), 7.39-7.40 (m, 2H), 7.26-7.25 (m, 4H), 6.32-6.24 (m, 1H), 5.10-5.05 (m, 2H), 4.78 (d, J=6.4 Hz, 2H), 4.55 (s, 1H), 3.05-3.04 (m, 2H), 1.60 (s, 3H), 1.38 (s, 3H).

The synthetic route of 4152-90-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HANDOK INC.; Lee, Jin-Hwa; Kim, Seung-Yong; Kim, Do-Ran; Ahn, Koo-Hyeon; Lee, Gwi-Bin; Kim, Doo-Seop; Hwang, Hyun-Sook; (74 pag.)US2017/204101; (2017); A1;,
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Electric Literature of 6579-54-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6579-54-0 name is 2,6-Dichlorobenzenesulfonyl chloride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: A solution of the appropriate acid halide fragments (4.8 mmol)in dry pyridine (5 mL) was dropwise added to a well-stirredmixture of the intermediate 3-amino-substituted rutaecarpine 5(4 mmol) in dry pyridine (50 mL) at room temperature. The reactionwasstirred for 30 min and monitored by TLC. After the reactioncompleted, the pH was adjusted to neutral with dilute hydrochloricacid. The pyridine and residual sulfonyl chloride were distilledunder reduced pressure. The mixture was extracted with an ethylacetate-water system. The aqueous layer was discarded and ethyl acetate was evaporated to obtain crude product. The crude productwas washed with water and dried under vacuum. The solid residuewas purified by flash chromatography on silica gel with ethyl acetate/petroleum ether (1:1) elution to provide the desired derivatives6a-6p, 7a-7c, and 8a.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dichlorobenzenesulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Article; Wu, Mingfei; Ma, Jie; Ji, Lijun; Wang, Min; Han, Jianfei; Li, Zeng; European Journal of Medicinal Chemistry; vol. 177; (2019); p. 198 – 211;,
Chloride – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, 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 461432-23-5, Formula: C15H14BrClO

To the 20 cc THF and 20 cc Toluene added 0.25 mole 2-ehloro-5-bromo-4′- ethoxydiphenylmethane under argon atmosphere. Cooled the reaction mass to – 78 C. Slowly added n-Butyl lithium (1.9 M in hexane) at – 78 C and stirred for 30 min. Slowly added 20 % Ammonium chloride solution to the reaction mass. Brought the reaction mass to ambient temperature and stirred for 30 min. Settled and separated layers. Extracted the aqueous layer with 50 cc toluene. Washed the combined organic layer with 500 cc brine solution. Distilled out the toluene and charged heptanes, stirred for 2 – 3 hrs at ambient temperature. Filtered the product and dried the product at 45 – 50C under reduced pressure to get 93 % titled compound. Mass: (m+1) 247 m/z found 247.1 1 HPLC purity: 96.33 %

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; HARMAN FINOCHEM LIMITED; KADAM, Vijay Trimbak; SAIKRISHNA; CHOUDHARE, Tukaram Sarjerao; MINHAS, Harpreet Singh; MINHAS, Gurpreet Singh; (26 pag.)WO2016/147197; (2016); A1;,
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Application of 39226-95-4, A common heterocyclic compound, 39226-95-4, name is 2,3-Dichlorobenzylamine, molecular formula is C7H7Cl2N, 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: Under nitrogen atmosphere, a Schlenk tube was sequentially charged with cyclicdiaryliodonium salt (1.0 equiv), copper catalyst A1 or A2 (5.0 mol%), Na2CO3 (3.0 equiv) anddichloromethane (0.05 M). After the mixture was chilled to proper temperature, the appropriateamine (1.2 equiv) was added and stirred for the time indicated in the experimental procedures.The reaction mixture was filtered through a plug of celite with ethyl acetate. The filtrate wasconcentrated under reduced pressure, and the residue was purified by column chromatographyon silica gel to deliver the corresponding product.

The synthetic route of 39226-95-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Kun; Duan, Longhui; Xu, Shibo; Jiang, Julong; Fu, Yao; Gu, Zhenhua; Chem; vol. 4; 3; (2018); p. 599 – 612;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, 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. Recommanded Product: 210532-25-5

3,5-Difluorobenzesulfonyl chloride (1 eq., 3.9 g, 18.4 mmol) was added portion-wise to a stirred solution of 6,6-dimethyl-3-[4-(4-methyl-piperazin-l-yl)-2-nitro-benzoylamino]- 5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-2-carboxylic acid ethyl ester dihydrochloride (10 g, 18.4 mmol) and N,N-diisopropylethylamine (6 eq., 19.3 mL, 110.4 mmol) in dry dichloromethane (100 mL) at room temperature. Stirring was continued for 4 hours. The reaction mixture was diluted with dichloromethane (100 mL) then washed with saturated sodium hydrogenocarbonate (150 mL), dried over sodium sulfate, evaporated to dryness and purified by flash chromatography on silica gel, using acetone as eluant. The title compound was obtained as yellow solid (9 g, 65% yield). IH-NMR (400 MHz), delta (ppm, DMSOtZ6): 10.71 (s, IH), 7.69-7.62 (m, 4H), 7.47 (d, J2=2.44 Hz, IH), 7.29 (dd, Jl=9.03 Hz, J2=2.44 Hz, IH), 4.58 (s, 2H), 4.43 (q, J=7.07 Hz, 2H), 3.41 (m, 4H), 2.50 (m, 4H), 2.26 (s, 3H), 1.67 (s, 6H), 1.35 (t, J=7.07 Hz, 3H).

The synthetic route of 210532-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; WO2007/68637; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 14752-66-0,Some common heterocyclic compound, 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, molecular formula is C6H4ClNaO2S, 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: I2 (0.5 mmol) was added to a solution of alkynes (0.5 mmol),sodium benzenesulfnates (1.0 mmol) and DTBP (1.0 mmol)in C2H5OH: H2O (2 mL:2 mL), and the reaction mixture wasstirred and heated at 60C for 2.0 h. Then, the mixture wascooled to room temperature, quenched by Na2S2O3, dilutedwithwaterandextractedbyCH2Cl2 (10mL ×3).Thecombined organic layer was washed with water and dried over anhydrousNa2SO4. The solvent was removed in vacuum and the targetcompound was obtained by column chromatography on silicagel (petroleum ether: ethyl acetate = 15: 1, v: v).

The synthetic route of 14752-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bi, Wenzhu; Ren, Chunyan; Jia, Linguo; Xia, Xiaoyi; Chen, Xi; Chen, Xiaolan; Zhao, Yufen; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 192; 4; (2017); p. 391 – 396;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics