Category: chlorides-buliding-blocks

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,
Chlorides – an overview | ScienceDirect Topics

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

The chemical industry reduces the impact on the environment during synthesis 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, I believe this compound will play a more active role in future production and life. 60811-21-4

A mixture of 4-bromo-2-chloro-l-fluorobenzene (8.04 g) and sodium methylthiolate(3.05 g) in DMF (25 ml) was heated at 50 C for 2.5 h. Water was added and the mixture wasextracted with ether (three times). The organic extracts were washed with water (twice), dried(MgSO4), and evaporated to give the sub-title compound (8.93 g).1K NMR CDC13: 6 7.54 (1H, d), 7.34 (1H, dd), 7.02 (1H, dd), 2.47 (3H, s).

The chemical industry reduces the impact on the environment during synthesis 60811-21-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/21759; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1996-29-8, The chemical industry reduces the impact on the environment during synthesis 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, I believe this compound will play a more active role in future production and life.

Under argon atmosphere, a mixture of X-Phos (750 mg; 1.53 mmol), l-bromo-4-chloro-2-fluoro-benzene (1.93 mL; 15.31 mmol), ieri-butyl 4-[(4, 4,5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)methylene]piperidine- 1 -carboxylate (5 500 mg;, 15.31 mmol), Pd dba3 (708 mg; 0.76 mmol) and K3P04 (4 975 mg; 22.97 mmol) in a mixture of H20 (5 mL) and dioxane (100 mL) was heated to 100 C and stirred for 2 h. After cooling down to rt, H20 and EA were added. The organic layer was separated, washed with brine, dried over MgS04, filtered and concentrated to dryness. The residue was purified by column chromatography (silica gel;PE: EA; 30:1 ; v/v) to afford feri-butyl 4-[(4-chloro-2-fluoro-phenyl)methylene]piperidine-l- carboxylate (4 000 mg) as a white solid. (0255) MS xn/z (+ESI): 311.1, 313.1 [M-/-Bu+HCOOH]+. (0256) ?H-NMR (400 MHz, CDC13) d ppm: 7.10 – 7.06 (m, 3H), 6.20 (s, 1H), 3.51 (t, J= 5.6 Hz, 2H), 3.41 (t, J = 5.6 Hz, 2H), 2.36 – 2.30 (m, 4H), 1.48 (s, 9H).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-chloro-2-fluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BASILEA PHARMACEUTICA INTERNATIONAL AG; RICHALET, Florian; EL SHEMERLY, Mahmoud; LANE, Heidi; (43 pag.)WO2019/115709; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13078-79-0, The chemical industry reduces the impact on the environment during synthesis 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, I believe this compound will play a more active role in future production and life.

General procedure: A solution of 24 (1.0 equiv.), HOBt (1.1 equiv.) and EDC (1.5 equiv.) in DMF (1.3 mmol/mL) was stirred at rt for 15 minutes. The appropriate amine (2.0 equiv.) was added and the resulting solution was stirred at rt for 5 hours. Reaction media was diluted with water and aqueous phase was extracted 3 times with EtOAc. Combined organic layers were washed successively with a solution of HCl 1N, a saturated solution of NaHCO3 and brine, dried over Na2SO4 and concentrated. The resulting solid was then purified by column chromatography on silica gel using the appropriate heptanes:EtOAc mixture.

The chemical industry reduces the impact on the environment during synthesis 2-(3-Chlorophenyl)ethanamine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Bollenbach, Maud; Lugnier, Claire; Kremer, Melanie; Salvat, Eric; Megat, Salim; Bihel, Frederic; Bourguignon, Jean-Jacques; Barrot, Michel; Schmitt, Martine; European Journal of Medicinal Chemistry; vol. 177; (2019); p. 269 – 290;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

94-97-3, Adding some certain compound to certain chemical reactions, such as: 94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole, 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 94-97-3.

General procedure: A mixture of azole (0.2 mmol), ketone (0.3 mmol, 1.5equiv.), NaHCO3 (33.6 mg, 2.0 equiv.), I2 (101.6 mg, 2.0 equiv.), and 1,2-dichloroethane (2 mL) was stirred at 80 C for 24 h. After cooling to room temperature, the reaction mixture was quenched with a saturated solution of Na2S2O3 (5 mL) and extracted with ethyl acetate (3×5 mL). The combined organic phases were washed with brine (10 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash column chromatograph, using a mixture of petroleum ether and ethyl acetate (5:1-2:1) as eluent to afford the corresponding products. The identity and purity of the products was confirmed by 1H and 13C NMR spectroscopic analysis.

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 94-97-3.

Reference:
Article; Chen, Wenlin; Yan, Rulong; Tang, Dong; Guo, Shuaibo; Meng, Xu; Chen, Baohua; Tetrahedron; vol. 68; 38; (2012); p. 7956 – 7959;,
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 6775-78-6 as follows. 6775-78-6

b) 3-Bromo-6-chloroimidazo[1,2-b]pyridazine Bromine (3.8 mL, 74.19 mmol) was added dropwise to a solution of 6-chloroimidazo [1,2-b]pyridazine (preparation 1 a, 4.8 g, 31.06 mmol) in glacial acetic acid (80 mL) and the resulting mixture was stirred at room temperature for 20 minutes. The precipitate formed was collected by filtration, washed with diethyl ether several times and dried in vacuo. The solid obtained was partitioned between ethyl acetate and a saturated aqueous solution of potassium carbonate. The organic layer was separated and washed with a saturated aqueous solution of potassium carbonate (x3), dried over magnesium sulphate and the solvent removed under reduced pressure. The crude was then treated with pentane, filtered and the solid obtained was dried in vacuo to yield the title compound (6.6 g, 92%) as a pale yellow solid. LRMS (m/z): 232 (M+1)+. 1H-NMR delta (300 MHz, CDCl3):7.13 (d, 1H), 7.80 (s, 1H), 7.92 (d, 1H).

According to the analysis of related databases, 6775-78-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Almirall, S.A.; EP2463289; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 363-51-9, name is 2-Chloro-6-fluoroaniline, 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 363-51-9, 363-51-9

A mixture of acetic anhydride (17.1 mL, 181 mmol) in formic acid (75 mL) was stirred at 90 C. for 10 minutes. 2-Chloro-6-fluoroaniline (22.0 g, 151 mmol) was then added and the reaction mixture was heated to 90 C. for 6 hrs. After cooling to r.t., water was added and the precipitated product was collected via filtration, washed with water, and air dried to afford N-(2-chloro-6-fluorophenyl)formamide as a white solid. The crude product obtained was used directly in the next step without further purification. LCMS calculated for C7H6ClFNO (M+H)+: m/z=174.0; Found 174.0.

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-Chloro-6-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Incyte Corporation; Hummel, Joshua; Nguyen, Minh; Sokolsky, Alexander; Vechorkin, Oleg; Ye, Qinda; Yao, Wenqing; (72 pag.)US2019/315717; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 64628-73-5, name is 3-Chloro-4-(trifluoromethoxy)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 64628-73-5

An ice-cold mixture of 98% H2SO4 (0.75 mL) and water (2.25 mL) was added to 3-chloro-4-(trifluoromethoxy)aniline (53) (1 .00 g, 4.73 mmol) and the resulting salt was crushed (using a glass rod) and cooled in an ice bath. A solution Of NaNO2 (359 mg, 5.20 mmol) in cold water (0.75 mL, then 0.25 mL) was added drop-wise, and the mixture was stirred at 0 0C for 12 min. A solution of urea (42.6 mg, 0.709 mmol) in cold water (0.25 mL) was added, and the mixture was stirred at 0 0C for 3 min. Finally, a solution of KI (1.65 g, 9.94 mmol) in cold water (1.6 mL, then 0.2 mL) was added slowly, and the mixture was stirred at room temperature for 10 min, and then at 52 C for 2 h. The resulting cooled mixture was diluted with ice-water (45 mL) and extracted with CH2Cl2 (4x 50 mL). The extracts were sequentially washed with an aqueous solution of Na2SO3 (30 mL of 0.5%) and then with water (40 mL) and finally concentrated carefully under reduced pressure at 17 C. The resulting oil was chromatographed on silica gel, eluting with pentane, to give 2-chloro-4-iodo- 1 -(trifluoromethoxy)benzene (54) (1.24 g, 81%) as a colourless oil (a white solid on freezing); 1H NMR (CDCl3) delta 7.82 (d, J = 2.1 Hz, 1 H), 7.61 (dd, J = 8.6, 2.1 Hz, 1 H), 7.05 (dq, J = 8.6, 2.0 Hz, 1 H); HRAPCIMS calcd for C7H3ClF3IO mlz (M+) 323.8834, 321.8864, found 323.8834, 321.8861.

The synthetic route of 64628-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT; DENNY, William, Alexander; THOMPSON, Andrew, M.; BLASER, Adrian; MA, Zhenkun; PALMER, Brian, Desmond; SUTHERLAND, Hamish, Scott; KMENTOVA, Iveta; WO2011/14774; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 33863-76-2 name is 1-Bromo-3-chloro-5-fluorobenzene, 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. 33863-76-2

To a solution of 1-bromo-3-chloro-5-fluorobenzene (25 g, 120 mmol) in methanol (800 ml) was added sodium methoxide (64 g, 1180 mmol). The reaction was heated to reflux for 9 days. The reaction was then concentrated in vacuo to one fifth of the volume (150 ml), cooled, and water (1000 ml) added. The mixture was extracted with diethyl ether (3 x 150 ml). The combined organic extracts were washed with brine (2 x 100 ml), dried over Na2SO4 and evaporated to afford the title compound (24.6 g). 1HNMR (CDCI3): 3.80(s, 3H), 6.84(s, 1 H), 6.96(s, 1 H), 7.10 (s, 1 H)GCMS Rt=3.86min MS m/z 222 [MH]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-chloro-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER LIMITED; WO2008/135826; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics