Month: October 2020

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. 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, A new synthetic method of this compound is introduced below., 6579-54-0

EXAMPLE 34; 2,6-dichloro-N-(2-chloro-5-(4-(4-morpholinyl)-6-quinolinyl)-3- pyridinyl)benzenesulfonamide; (Some starting materials may be obtained from Alfa Aesar, Ward Hills, MA) To a flame-dry 50 mL rb flask was added 2-chloro-5-(4-morpholinoquinolin-6-yl)pyridin-3-amine (0.07 g, 0.2 mmol) and THF (8 mL). The reaction mixture was cooled to 0 0C followed by adding sodium bis(trimethylsilyl)amide, 1.0m solution in tetrahydrofuran (0.4 ml, 0.4 mmol). After the addition, it was continued to stir at 0 0C under N2. After 30 min, 2,6-dichlorobenzene- 1-sulfonyl chloride (0.07 g, 0.3 mmol) was added into the reaction mixture. After the addition, it was continued to stir at 0 0C then slowly warmed up to rt overnight. The reaction was quenched with water. The solvent was concentrated. The residue was partitioned between EtOAc/water. The organic layer was washed with brine, dried over MgSO4 and concentrated. The crude product was purified using SiO2 (12 g) chromatography with DCM:EtOAc:MeOH=70%:26%:4% as the solvent system to afford the desired product as light yellow solid (63.0 mg). MS (ESI pos. ion) m/z: calc’d for C24H19Cl3N4O3S: 548.1; found: 549.4 (M+l). 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 3.21 – 3.38 (m, 4 H) 3.93 – 4.11 (m, 4 H) 6.94 (d, J=4.97 Hz, 1 H) 7.33 – 7.44 (m, 1 H) 7.45 – 7.55 (m, 2 H) 7.85 (dd, J=8.77, 2.05 Hz, 1 H) 8.18 (d, J=8.77 Hz, 1 H) 8.25 (d, ./=1.90 Hz, 1 H) 8.39 – 8.50 (m, 2 H) 8.81 (d, J=4.97 Hz, 1 H).

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; AMGEN INC.; WO2009/155121; (2009); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

627-42-9, A common compound: 627-42-9, name is 2-Methoxyethyl chloride, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

The ether-functionalized ionic liquids 1-(2-methoxyethyl)-3-methylimidazolium threonine ([C1OC2Mim][Thr]) and 1-(2-ethoxyethyl)-3-methylimidazolium threonine ([C2OC2Mim][Thr]) were prepared according to the method as described in the literatures [32]. Under the protection of nitrogen, 2-chloroethyl methyl ether (122 ml, 1.1 mol) was added to N-methylimidazole (85 ml,1.0 mol) with a constant pressure funnel in round-bottom flaskwas stirred at 353.15 K for 48 h. After the reaction, extraction with ethyl acetate (3 ¡Á 60 mL) and drying under vacuum at 353.15 K for48 h to obtain pale yellow liquid [C1OC2Mim][Cl]. Next,[C1OC2Mim][OH] was synthesized from [C1OC2mim][Cl] by the useof activated anion-exchange resin. Then aqueous [C1OC2Mim][OH] was added to a slightly excess threonine aqueous solution and stirred for 48 h. Finally, excess water was evaporated under reduced pressure. To this reaction mixture was added the mixed solvent ethanol/acetonitrile (volumetric ratio = 9/1), and it was stirred befittingly. The mixture was then filtered to remove excess threonine.The product was dried under vacuum at 353.15 K for 48 h to obtain the target ionic liquid [C1OC2Mim][Thr]. Similarly, [C2OC2Mim] [Thr] was also synthesized according to the above method. Fig. 1 shows the synthetic route of the ionic liquids [C1OC2Mim][Thr] and [C2OC2Mim][Thr]. Based on the mass loss of product, the yields were estimated approximately 80%. The ether groups are abbreviated as CmOCn-, where m stands for the number of carbon atoms inthe alkyl tail and n stands for the number of carbon atoms of the spacer between the cationic nitrogen atom and the ether oxygen atom. The 3-methylimidazolium and the threonine are abbreviated as Mim and Thr, respectively.

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-Methoxyethyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Duo; Li, Biao; Hong, Mei; Kong, Yu-Xia; Tong, Jing; Xu, Wei-Guo; Journal of Molecular Liquids; vol. 304; (2020);,
Chloride – Wikipedia,
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112-26-5, A common compound: 112-26-5, name is 1,2-Bis(2-chloroethoxy)ethane, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

A mixture of 1,2-bis(2-chloroethoxy)ethane (5.00 g, 26.73 mmol, 1.00 Eq) and NaI (12.02 g, 80.19 mmol, 3.00 Eq) in acetone (50 mL) was stirred at 56 C. for 72 hr under N2 atmosphere. Most solid sodium chloride was formed. After filtration of the resulting sodium chloride, the solution was concentrated in vacuum. The residue was diluted with CH2Cl2 (200 mL) and the solution was washed with water (100 mL), dried over Na2SO4 and evaporated in vacuum. The residue was purified by chromatography on silica gel (eluting with PE_EA=100:1 to 10:1) to afford the pure product 1,2-bis(2-iodoethoxy)ethane (9.10 g, 24.60 mmol, 92.02% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 3.80 (t, J=6.90 Hz, 4H), 3.70 (s, 4H), 3.29 (t, J=6.78 Hz, 4H).

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, 1,2-Bis(2-chloroethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Novira Therapeutics, Inc.; Hartman, George D.; Kuduk, Scott; (85 pag.)US2016/272599; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

622-24-2, Name is (2-Chloroethyl)benzene, 622-24-2, 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.

methyl 5-(phenethylamino)-2-(phenylsulfonamido)benzoate (13) To a round-bottom-flask under nitrogen methyl 5-amino-2-(phenylsulfonamido)benzoate 12 (184 mg, 0.6 mmol, 1.0 equiv.) and dry DMF (20 mL) were added. This was followed by addition of K2CO3 (691 mg, 3 mmol, 5.0 equiv.) and 1 -(2-chloroethyl)benzene (0.199 mL, 211 mg, 1.5 mmol, 2.5 equiv.) and the mixture was heated at 120 C for 16 hours. The reaction mixture was then allowed to cool down to room temperature and diluted with ice H20 (20 mL). The resulting mixture was extracted with Et^O (2 x 30 mL). All the organic extracts were combined, dried over NaS04 and concentrated. The crude product was purified by flash column chromatography (ethyl acetate_hexanes=50:50) on silica gel to afford 13 (211 mg, 85%) as yellow oil. lH NMR (400 MHz, CDC13) delta 7.62-7.12 (m, 11H), 6.71-6.64 (m, 2H), 3.92-3.69 (m, 6H), 3.03-2.85 (m, 2H); 1 C NMR (100 MHz, CDC13) delta 166.57, 146.52, 139.75, 138.58, 133.08, 132.16, 131.83, 128.78, 128.64, 128.41, 127.73, 127.38, 126.31, 117.75, 117.00, 53.61, 52.04, 35.58.

Statistics shows that (2-Chloroethyl)benzene is playing an increasingly important role. we look forward to future research findings about 622-24-2.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; NIKOLOVSKA-COLESKA, Zaneta; STUCKEY, Jeanne A.; MADY, Ahmed; MIAO, Lei; (140 pag.)WO2016/172218; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

98446-49-2, 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. 98446-49-2, name is 2,4-Dichloro-5-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 4 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide 2,4-Dichloro-5-methoxyaniline (5.00 g, 26 mmol) and cyanoacetic acid (2.28 g, 26.8 mmol) were mixed in 50 mL of tetrahydrofuran until a solution formed. This solution was heated to reflux and 1,3-diisopropylcarbodiimide (4.2 mL, 26.8 mmol) was added dropwise. After 30 minutes the mixture was cooled to ~15 C. in an ice-bath. The solid was collected by filtration and washed with tetrahydrofuran. The filtrate was slowly poured into water and stirred for 30 minutes. The white solid was collected by filtration, washed with water, and was then dissolved in 500 mL of ethyl acetate. The solution was dried over sodium sulfate and concentrated in vacuo to give 5.9 g (88%) of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide as a white solid, mp 180-181 C.; 1H NMR (400 MHz, DMSO-d6) delta 3.84 (s, 3H), 4.02 (s, 2H), 7.58 (s, 1 H), 7.66 (s, 1 H), 10.00 (s, 1 H); MS (ES) m/z257.0, 259.0 (M-H)- Analysis for C10H8Cl2N2O2; Calcd: C, 46.36; H, 3.11; N, 10.81. Found: C, 46.25; H, 3.10; N, 10.85.

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; Wyeth Holdings Corporation; US2005/43537; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, molecular formula is C6H3Cl3O2S, 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. 6579-54-0

General procedure: To a solution of amine 7 (41 mg, 0.1 mmol) indry pyridine (2 mL), substituted benzenesulfonyl chloride (1.52 eq.) was added. The reaction mixturewas kept at r.t. overnight and poured into a mixture of 1 M hydrochloric acid (10 mL) and ethyl acetate(10 mL) while being vigorously stirred. The organic phase was separated and concentrated in vacuo.The residue was dissolved in a mixture of methanol (10 mL) and 5 M sodium hydroxide solution(5 mL) and kept at r.t. for 1 h. The mixture was concentrated in vacuo to remove the methanol andwas diluted with water (3 mL) and ltered. The clear water phase was washed with ethyl acetate(3 mL x 2) and then concentrated hydrochloric acid was added dropwise until pH = 4. The mixturewas filtered to afford the desired sulfonamide 9a-9n as yellow solids (yield: 30-80%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6579-54-0, its application will become more common.

Reference:
Article; Wang, Penghui; Jiang, Lulu; Cao, Yang; Ye, Deyong; Zhou, Lu; Molecules; vol. 23; 6; (2018);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 626-43-7, name is 3,5-Dichloroaniline, 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 626-43-7. 626-43-7

General procedure: PdTBAB (1 mol % Pd in 250 mg of TBAB synthetized in scCO2), alcohol (2 mmol, 2 eq), amine (1 mmol, 1 eq) and anisole (1 mL) were introduced into a sealed tube under argon. The reaction was then heated at 140 C for 12 h. After cooling the reaction at room temperature, the mixture was filtrated on Celite and washed with Et2O and the filtrate was concentrated under vacuum. The crude oil was purified by column chromatography.

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 3,5-Dichloroaniline.

Reference:
Article; Cacciuttolo, Bastien; Pascu, Oana; Aymonier, Cyril; Pucheault, Mathieu; Molecules; vol. 21; 8; (2016);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, 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 1996-30-1. 1996-30-1

Intermediate 7A. 3-Chloro-l-(5-chloro-2-fluorophenyl)propan-l-one: In a flame-dried 3 -neck flask, 2-bromo-4-chloro-l-fluorobenzene (2.0 g, 9.55 mmol) was dissolved in THF (anhydrous) (28.9 mL) under argon. Isopropylmagnesium chloride (2 M in THF) (5.01 mL, 10.03 mmol) was added, and the reaction was stirred at rt. To this solution was added zinc chloride (0.5 M in THF) (20.44 mL, 10.22 mmol) and the mixture was stirred at ambient temperature for 40 min. To the reaction was then added Pd(PPh3)4 (0.276 g, 0.239 mmol), and the mixture was cooled to 0 C. A solution of 3- chloropropanoyl chloride (0.981 mL, 10.22 mmol) in THF (2.89 mL) was added, and the reaction was stirred for 2 h at 0 C. The reaction mixture was then quenched with 3 N HCl, diluted with water, and extracted with Et20 (3x). The combined organics were dried (MgS04), filtered and evaporated to yield a grainy yellow liquid, which was purified using silica gel chromatography to obtain a colorless oil, 3-chloro-l-(5-chloro-2- fluorophenyl)propan-l-one (0.405 g, 19%). MS (ESI) m/z: 221.0 (M+H)+. 1H NMR (400 MHz, CDC13) delta 7.88 (dd, J = 6.3, 2.8 Hz, 1H), 7.51 (ddd, J = 8.8, 4.3, 2.8 Hz, 1H), 7.13 (dd, J = 10.2, 8.7 Hz, 1H), 3.94 – 3.88 (m, 2H), 3.46 (td, J = 6.6, 3.2 Hz, 2H) ppm.

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-Bromo-4-fluorochlorobenzene.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LAM, Patrick Y.S.; CLARK, Charles G.; CORTE, James R.; EWING, William R.; GILLIGAN, Paul J.; JEON, Yoon; YANG, Wu; SMITH, Leon, M., II.; WANG, Yufeng; WO2013/22814; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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

Preparation of N-[2-(4-chlorophenoxy)phenyl]-3-acetamido-3-phenylpropanamide STX1858 C23H21ClN2O3, MW: 408.88 EPO To a pre-stirred solution of iV-acetyl-3-phenyl-beta-alanine (104 mg, 0.50 mmol), EDC (265 mg, 1.38 mmol), triethylamine (70 mg, 0.69 mmol) and DMAP (6 mg, 0.046 mmol) in anhydrous DCM (25 ml), was added 2-(4-chlorophenoxy)phenylamine (100 mg, 0.46 mmol). This mixture was then allowed to stir at room temperature for 14 h. The reaction mixture was washed with 2.5M NaOH (20 ml), 2M HCl (20 ml) and the organics were then dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (eluant; DCM to 9:1 DCM:MeOH) then proceeded to afford the desired product as an off-white solid (58.9 mg, 31%). 1H NMR (270 MHz, CDCl3): delta 2.03 (3H, s, CH3), 2.83-2.99 (2H, m, CH2), 5.30-5.40 (IH, m, CH), 6.73-6.77 (IH, dd, J= 1.5, 8.2 Hz, Ar-H), 6.83-6.86 (2H, m, Ar-H), 6.95-7.03 (IH, td, J= 1.7, 7.9 Hz, Ar-H), 7.05-7.11 (IH, td, J= 1.7, 7.9 Hz, Ar-H), 7.19-7.30 (7H, m, Ar-H), 7.60 (IH, br s, Ar-H), 8.22-8.25 ppm (IH, dd, J – 1.5, 8.0 Hz, Ar-H). LCMS: M+H: 409.44 HPLC: 98.66% (2.268 mins, isocratic 90% acetonitrile, 10% water at 1 rnl/min).

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 2-(4-Chlorophenoxy)aniline.

Reference:
Patent; STERIX LIMITED; WO2007/3934; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

10061-02-6,Some common heterocyclic compound, 10061-02-6, name is trans-1,3-Dichloropropene, molecular formula is C3H4Cl2, 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 mixture of 0.01 mol (1.0 g) of pentane-2,4-dione, 0.001 mol (0.1 g) of sodium butylate, and 60 mL of anhydrous acetonitrile was irradiated at constant stirring for 20 min. The mixture was then cooled to room temperature and was charged with 0.015 mol of the corresponding alkene 4. Next, irradiation was continued for 2 h to complete conversion of pentane-2,4-dione. Upon completion of the reaction (GLC monitoring) the mixture was cooled to room temperature, washed with water, and extracted with chloroform. The organiclayer was dried with potassium carbonate and evaporated. The residue was distilled in a vacuum.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 10061-02-6, its application will become more common.

Reference:
Letter; Borisova, Yu. G.; Raskildina; Zlotskii; Russian Journal of General Chemistry; vol. 86; 9; (2016); p. 2126 – 2128; Zh. Obshch. Khim.; vol. 86; 9; (2016); p. 1564 – 1566,3;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics