Month: August 2021

These common heterocyclic compound, 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl chloride, 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. Application In Synthesis of 2,4-Dimethoxybenzene-1-sulfonyl chloride

B) 3-(2-Chlorophenyl)-1-[(2,4-dimethoxyphenyl)sulphonyl]-5-methyl-3-[2-oxo-2-[4-(2-pyridyl)-1-piperazinyl]ethyl]-1,3-dihydro-2H-indol-2-one 0.0335 g of 60% sodium hydride in oil is added, at RT, to a mixture of 0.3 g of the compound obtained in the preceding step in 10 ml of THF, and the mixture is stirred for 30 minutes. 0.2 g of 2,4-dimethoxybenzenesulphonyl chloride is then added and the mixture is stirred at RT for 1 hour. 50 ml of water are added to the reaction mixture and the resulting mixture is extracted with EtOAc, the organic phase is dried over Na2SO4 and the solvent is evaporated off under vacuum.The residue is chromatographed on silica gel, eluding with a DCM/MeOH mixture (98/2; v/v).0.32 g of the expected product is obtained after crystallization from iso ether, m.p.=239 C.

The synthetic route of 2,4-Dimethoxybenzene-1-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Di Malta, Alain; Garcia, Georges; Roux, Richard; Schoentjes, Bruno; Serradeil-Le Gal, Claudine; Tonnerre, Bernard; Wagnon, Jean; US2004/180878; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, 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 918538-05-3, name: 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine

General procedure: To a solution of 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), 1-methyl-1H-imidazol-4-amine hydrochloride (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, and friends who are interested can also refer to it.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); 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 18282-59-2 as follows. Quality Control of 4-Bromo-1,2-dichlorobenzene

A. 1-Bromo-4,5-dichloro-2-nitro-benzene. 4-Bromo-1,2-dichlorobenzene (10.5 g, 46.3 mmol) was added to 25 mL concentrated sulfuric acid at 0° C. A 1:1 mixture of 70percent nitric acid and concentrated sulfuric acid (20 mL) was added dropwise over 40 min. The reaction mixture was allowed to warm to ambient temperature with stirring over 0.5 h, then was poured onto cracked ice. The resulting mixture was filtered through paper, and the collected solids were washed with water (5*) and then dried at 45° C. under reduced pressure for 30 min to provide 10.7 g of an 88:12 mixture of desired nitroarene to starting material. Recrystalization from absolute ethanol provided 4.76 g of long yellow needles corresponding to a 20:1 mixture of product to starting material. The mother liquor was concentrated and recrystallized twice to provide an additional 1.18 g of product (17:1 mixture with recovered starting material). TLC (silica gel, 1:1 hexanes/EtOAc): Rf=0.45. 1H NMR (400 MHz, CDCl3): 7.95 (s, 1H), 7.80 (s, 1H).

According to the analysis of related databases, 18282-59-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allison, Brett; McAtee, Laura C.; Phuong, Victor K.; Rabinowitz, Michael H.; Shankley, Nigel P.; US2004/224983; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 33406-96-1, A common heterocyclic compound, 33406-96-1, name is 1-Chloro-4-fluoro-2-methylbenzene, molecular formula is C7H6ClF, 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: A mixture of aryl chloride (0.125 mmol), aryl boronic acid (0.15 mmol) and K4PO3 (0.25 mmol), catalyst (0.000125 mmol) in H2O (0.1 mL), isopropanol (0.1 mL) was stirred in a test tube at 45 C. After the reaction was completed, cooled to room temperature and the mixture was extracted with CH2Cl2 and dried over Na2SO4. The solvent was removed under vacuum. The product was purified by flash chromatography on a silica gel column. The characterization of all coupling products see Supporting Information.

The synthetic route of 33406-96-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Fangwai; Li, Yanji; Liu, Guiyan; Lu, Qingwen; Ni, Chang; Zeng, Yongfei; Zhang, Rong; Zhang, Xue; Zhang, Yingying; Zhao, Yuxuan; Tetrahedron Letters; (2019);,
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. 1939-99-7, name is Phenylmethanesulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., name: Phenylmethanesulfonyl chloride

Step 1 : N-re^butyl-1 -phenylmethanesulfonamide To a solution of teri-butylamine (2 g, 27.3 mmol) in dichloromethane (90 mL) was added N,N-diisopropylethylamine (5.7 mL, 32.8 mmol), followed by phenylmethanesulfonyl chloride (6.25 g, 32.8 mmol) and the reaction was stirred at ambient temperature for 16 hours. The reaction was then diluted with dichloromethane, washed with water and brine, dried with MgS04, and purified by silica gel column chromatography (0-50% EtOAc in heptane) to give N-teri-butyl-l-phenyl- methanesulfonamide (4.81 g, 77% yield). 1 H NMR (400 MHz, CDC13) delta 7.51 – 7.44 (m, 2H), 7.41 (dd, J= 4.9, 2.0 Hz, 3H), 4.49 (s, 2H), 4.27 (s, 1H), 1.68 (s, 6H); LCMS (m/z) ES+ 228 [M+l]+.

According to the analysis of related databases, 1939-99-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; FAUBER, Benjamin; RENE, Olivier; WO2013/92941; (2013); 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 1996-29-8 as follows. Safety of 1-Bromo-4-chloro-2-fluorobenzene

To a solution of 1-bromo-4-chloro-2-fluorobenzene (10.0 g, 47.8 mmol) in dry THF (300 ml.) at -78 C under nitrogen was added LDA (2.0 M solution in THF, 31 ml_, 62.1 mmol) dropwise and the mixture was stirred at -78 C for 15 min. DMF (7.00 g, 95.8 mmol) was added and the mixture was allowed to warm to room temperature. The reaction mixture was quenched with a saturated aqueous NH4CI solution and the mixture was extracted with EtOAc (400 ml. x 3). The combined organic extracts were washed with brine (300 ml_), dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (100% Pet. Ether) to give the title compound (4.0 g, 35%) as a white solid, which was used directly in the next step.

According to the analysis of related databases, 1996-29-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTXT PTY LIMITED; MORROW, Benjamin, Joseph; CAMERINO, Michelle, Ang; WALKER, Scott, Raymond; STEVENSON, Graeme, Irvine; STUPPLE, Paul, Anthony; (266 pag.)WO2019/219820; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 367-22-6, name is 4-Chloro-3-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 367-22-6, category: chlorides-buliding-blocks

Step B: 4-Chloro-5-fluoro-2-iodo-phenylamine Iodine chloride (20.6 ml, 1M solution in DCM, 20.6 mmol) was added dropwise to a solution of 4-chloro-3-fluoroaniline (2 g, 13.7 mmol) in methanol (35 ml) at 0 C. and the reaction mixture was stirred for 1 h at room temperature. Volatiles were removed under reduced pressure, water was added and the mixture was extracted with dichloromethane. The combined organic layers were washed with water, dried with Na2SO4 and evaporated. The remaining residue was purified by chromatography with three consecutive columns (silica gel, heptane/EtOAc 98:2-93:7 and twice heptane/EtOAc 98:2-95:5) to obtain the title compound (2.51 g, 67%) as dark red solid. MS (ESI): 272.1 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloro-3-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; Hoffmann-La Roche Inc.; Ceccarelli, Simona M.; Conte, Aurelia; Kuehne, Holger; Kuhn, Bernd; Neidhart, Werner; Obst Sander, Ulrike; Rudolph, Markus; US2013/116234; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2613-34-5, The chemical industry reduces the impact on the environment during synthesis 2613-34-5, name is 3-Chloro-2,4-difluoroaniline, I believe this compound will play a more active role in future production and life.

3-Chloro-2,4-difluoro-(trifluoroacetamido)benzene. To a solution of 10.5 g (64.3 mmol) of 3-chloro-2,4-difluoroaniline in 25 mL of dioxane kept in an ice-bath was added dropwise 10 mL (14.8 g, 70.4 mmol) of trifluoroacetic anhydride. The solution was stirred at room temperature for 20 h. It was then added to 150 mL of ice-water and the mixture was stirred for 1 h. It was filtered, washed with water, and dried to leave an almost colorless solid 16.1 g (96%); mp 73-74 C.; 1 H NMR (CDCl3), 7.068 (m, 1), 7.976 (mb, 1), 8.146 (m, 1).

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, 3-Chloro-2,4-difluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; State of Oregon, acting by and through the Oregon State Board of Higher Education, acting for and on behalf of the Oregon Health Sciences University and the University of Oregon, Eugene Oregon; Acea Pharmaceuticals, Inc.; The Regents of the University of California; US5631373; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

51419-59-1, name is p-Tolylmethanesulfonyl 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. COA of Formula: C8H9ClO2S

A solution of 1-(4-Amino-phenyl)-3-pyridin-4-ylmethyl-urea (80 mg, 0.33 mmol) in DIVIF (3 mL) was added p-Tolyl-methanesulfonyl chloride (94.7 mg, 0.46 mmol) and TEA (168.4 mg, 1.65 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was washed H20 (10 mL) and extracted with EA (50 mL). The combined organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified by prep-HPLC (5-95; NH4HCO3) to give n- [4-(3 -pyridin-4-ylmethyl-ureido)-phenyl] -c-p-tolyl-methanesulfonamide (35 mg, yield 26percent) as a white solid. ?H NMR (400 IVIHz, DMSO-d6): oe = 9.49 (s, 1H), 8.68 (s, 1H), 8.51-8.49 (m, 2H), 7.37 (d, J 8.8 Hz, 2H), 7.28 (d, J 5.6 Hz, 2H), 7.18-7.13 (m, 4H), 7.08 (d, J= 8.8 Hz, 2H), 6.71 (t, J= 5.6 Hz, 1H), 4.32 (d, J 5.6 Hz, 2H), 4.29 (s, 2H), 2.29 (s, 3H). MS: m/z 410.9 (M+HH).

The synthetic route of 51419-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); 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. 261762-56-5, name is 1-Chloro-2-fluoro-3-methoxybenzene, A new synthetic method of this compound is introduced below., Formula: C7H6ClFO

1 g (6.2 mmol) 3-Chloro-2-fluoroanisole in 20 ml THF was cooled to -70 C. and 2.7 ml of a 2.5 M n-butyl lithium solution in hexane were added. After one hour at -70 3.93 ml DMF in 7 ml THF were added at -70 C. and the mixture is stirred another hour at -70 C. 15 ml of a 1 M aqueous hydrochloric acid were added and the reaction was warmed to ambient temperature over 18 hours. The reaction mixture was partitioned between diethyl ether and water. The aqueous phase was extracted with diethyl ether, the combined organic phases were washed with brine, dried over sodium sulfate and evaporated. The crude product was purified by chromatography on silica gel to yield 0.25 g 2-chloro-3-fluoro-4-methoxybenzaldehyde. 1H-NMR (CDCl3); delta=3.98 (s, 3H), 6.98 (dd, 1H), 7.75 (dd, 1H), 10.30 (s, 1H).

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; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; ASTRAZENECA AB; US2010/16338; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics