Category: 6579-54-0

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. 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 6579-54-0

General procedure: Benzenesulfonyl chloride (1 mmol) in butanone (5 mL) was heated with stirring to 40C, and cyanamide solution (50%)was added dropwise, then the temperature was raised to 60C and stirring continued for 3 h. The compound 7 (0. 8 mmol)was added and heated to 80C for 3 h. After cooling to 40C, the reaction mixture was poured into cold water while stirring, white crystals or powders were precipitated, filtered,washed with water, and dried. Analytically pure samples were obtained by recrystallization from aqueous ethanol.

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:
Article; Li, Jie; Zheng, Tu-Cai; Jin, Yi; Xu, Jian-Guo; Yu, Jian-Gang; Lv, Yan-Wen; Chemical and Pharmaceutical Bulletin; vol. 66; 1; (2018); p. 55 – 60;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, 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 6579-54-0. 6579-54-0

General procedure: A mixture of N-Boc-aminol (1 eq.) and KOH (3eq) in THF was stirred vigorously for 15 min. It was followed by the addition of required benzenesulfonyl chloride derivative (1.2eq) and subsiquent stirring of the reaction for 4-5h. After completion of the reaction (as per TLC), the reaction mixture was filtered to expel out the precipitated salt and the filterate thus obtained was concentrated under reduced pressure to obtain the crude product which was further purified by column chromatography (eluent EtOAc:Hexane).

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 2,6-Dichlorobenzenesulfonyl chloride.

Reference:
Article; Saxena, Anil K.; Sharma, Sugandha; Pandey, Atindra K.; Shukla, Praveen K.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 21; (2011); p. 6476 – 6481;,
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. 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. 6579-54-0

a) 2-[(Cyclopropylcarbamoyl)amino]-1H-benzimidazol-5-yl 2,6-dichlorobenzenesulfonate may be prepared in the following manner:To a suspension of 300 mg of 1-cyclopropyl-3-(5-hydroxy-1H-benzimidazol-2-yl)urea in 100 cm3 of acetone are added 186 mg of triethylamine and 349 mg of 2,6-dichlorobenzenesulfonyl chloride. After stirring overnight at a temperature in the region of 20 C., 90 mg of 2,6-dichlorobenzenesulfonyl chloride are added and the mixture is stirred for a further 24 hours. The reaction medium is evaporated to dryness under reduced pressure (2 kPa). The residue is taken up in 50 cm3 of water and then extracted with three times 40 cm3 of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure (0.5 kPa). After flash chromatography on a column of silica [eluent: dichloromethane/methanol (96.5/3.5 by volume)], the product obtained is solidified in 10 cm3 of diethyl ether and then filtered off, washed with three times 5 cm3 of diethyl ether and dried under reduced pressure over phosphorus pentoxide. 130 mg of 2-[(cyclopropylcarbamoyl)amino]-1H-benzimidazol-5-yl 2,6-dichlorobenzenesulfonate are obtained in the form of a cream-coloured powder, the characteristics of which are as follows:Melting point: melting at 160-165 C. (Koefler block)1H NMR spectrum at 400 MHz: 0.47 (m, 2H); 0.68 (m, 2H); 2.62 (m, 1H); 6.75 (dd, J=2.5 and 8.5 Hz, 1H); 7.09 (broad m, 1H); 7.24 (broad m, 1H); 7.30 (broad d, J=8.5 Hz, 1H); from 7.68 to 7.79 (m, 3H); 9.82 (broad m, 1H); 11.75 (broad m, 1H)Mass spectrum: MS (ES+): m/z=441 [MH+]

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:
Patent; AVENTIS PHARMA S.A.; US2008/194555; (2008); A1;,
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

2,6-Dichloro-3-nitrobenzenesulfonic acid Lithium hydroxide hydrate (12.64 g, 0.301 mol) was added to a solution of 2,6-dichlorobenzenesulfonyl chloride (35.53 g, 0.146 mol) in MeOH (600 mL) and the reaction was allowed to stir at room temperature for 3 hr. The reaction mixture was filtered to remove suspended solids and then concentrated. The resulting solid was dried in vacuo overnight to remove any residual MeOH. The solid was then dissolved in H2SO4 (300 mL) and chilled in an ice bath. A solution of H2S04 (35 mL) and HNO3 (13.2 mL) was slowly added to the above reaction over 90 min. The reaction was allowed to warm up to room temperature overnight and then slowly poured into ice water (1200 mL) and extracted with EtOAc. The combined organic layers were dried (MgSO4) and concentrated to yield 2,6-dichloro-3-nitrobenzenesulfonic acid (44.35 g, 99%) as the dihydrate. EI-MS (m/z) 270 (M-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; SmithKline Beecham Corporation; US6500863; (2002); B1;,
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. 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., 6579-54-0

b 2,6-dichlorobenzenesulfonamide A solution of 2,6-dichlorobenzenesulfonyl chloride (10.50 g, 42.77 mmol) in 100 mL of pyridine was added into 100 mL of pyridine dropwise while anhydrous ammonia gas was passing through the solution simultaneously for 4 hours at 0 C. The mixture was acidified to pH>1 with 6N aq. HCl, then extracted with ethyl acetate. The combined organic layer was then dried (Na2SO4) and concentrated to give the desired product (8.69 g, 90%). EI-MS (m/z) 225.0, 227.1 (M-).

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; Widdowson, Katherine Louisa; Jin, Qi; US2003/65170; (2003); A1;; ; Patent; Widdowson, Katherine Louisa; Jin, Qi; US2003/65188; (2003); A1;,
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

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

6579-54-0, The chemical industry reduces the impact on the environment during synthesis 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, I believe this compound will play a more active role in future production and life.

171 mg 3-[6-(2-Methoxy-phenyl)-pyrimidin-4-ylamino]-benzyl-ammonium chloride (prepared in Example 69) (0.5 mmol) was dissolved in 50 cm3 dry dichloromethane, 0.350 cm3 N,N-diisopropyl-ethylamine (259 mg, 2 mmol) was added and the mixture was cooled to 0 C. in an ice bath. After stirring it for 15 minutes 196 mg 2,6-dichlorobenzenesulfonyl-chloride (0.8 mmol) was added and the mixture was stirred for 2 hours at 0 C. and overnight at room temperature. Then 50 cm3 5% NaHCO3 solution was added and it was extracted three times with 50-50 cm3 of chloroform. The combined organic layer was washed with brine, dried over MgSO4, decolorized with activated carbon and evaporated under reduced pressure. The residual solid was recrystallized from minimal amount of acetonitrile and air-dried to give the desired product as an yellow solid. Yield: 34 mg (13%). For analitical results and compound identification see Table 1.

The chemical industry reduces the impact on the environment during synthesis 2,6-Dichlorobenzenesulfonyl chloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Greff, Zoltan; Varga, Zoltan; Keri, Gyoergy; Nemeth, Gabor; Oerfi, Laszlo; Szantai Kis, Csaba; US2012/258968; (2012); A1;,
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

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.

To a mixture of 2,4-dichloro-5-methylpyrimidine (4.17g, 25.6mmol) and 4-acetamidophenylboronic acid (5.Og, 27.9mmol) in DME (40ml) was added Et3N (8.92ml, 64.0mmol), H2O (4ml), and dichloro[l,r-bis(diphenylphosphino)ferrocenepalladium (2.8 Ig, 3.44mmol, 13%). The mixture was allowed to stir at reflux for 5hrs. After the mixture was cooled down to rt, the crude mixture was directly filtered on silica gel and eluted with EtOAc. The filtrate was concentrated in vacuo. Further purification was conducted by flash chromatography to afford Intermediate 1 (5.94g, 89%) as a white solid. LCMS: m/z 262 (M+H)+.[0246] To a stirred solution of chloropyrimidine (1.05g, 4.0mmol) in 1-butanol (10ml) was added N-Boc-amino-3-aniline (920mg, 4.4mmol) and the mixture was heated in the sealed tube at 18O0C for 1.5hr. The mixture was cooled down to rt and acidified with IN HCl (20ml). The aqueous layer was washed with EtOAc (50ml). The separated aqueous layer was basified with 2N NaOH to pH 8-9 and extracted with EtOAc (50ml*3). The combined organic layer was dried over Na2SO4, concentrated in vacuo, and purified by flash 5 chromatography to afford product Intermediate K (943mg, 71% as a light yellow solid. LCMS: m/z 334 (M+H)+.[02471 To a stirred suspension of aniline (250mg, 0.75mmol) in THF (5ml) was added DIPEA (157ml, 0.90mmol) and 2,6-dichlorobenzenesulfonyl chloride (203 mg, 0.83mmol) and the mixture containing intermediate K was stirred at reflux for 2hrs. After cooling down to rt, the mixture was diluted with EtOAc, washed with H?O, brine, and dried over Na2SO4. After concentrated in vacuo, the residue was purified by flash chromatography to give product 26 (299mg, 73%) as a light pink solid.1H-NMR (400MHz, d6-DMSO): 10.71 (s, IH), 10.16 (s, IH), 9.54 (s, IH), 8.34 (s, IH), 7.75- 7.69 (m, 5H), 7.60 (dd, 2H), 7.51 (dd, IH), 7.31 (dd, IH), 7.09 (t, IH), 6.66 (dd, IH), 2.25 (s, 3H), 2.08 (s, 3H); MS (EI) C25H2ICl2N5O3S: 542.2 (M+H)+.

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:
Patent; EXELIXIS, INC.; WO2007/89768; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics