Category: chlorides-buliding-blocks

Application of 2533-69-9,Some common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, molecular formula is C3H4Cl3NO, 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.

3) A solution of N-(4-methoxybutyl)-o-phenylenediamine in toluene was cooled to 0-10 C., and acetic acid (65.2 g, 1.09 mol) and methyl 2,2,2-trichloroacetimidate (70.3 g, 0.398 mol) were added. After stirring at 0-10 C. for 30 min, the mixture was stirred at 20-30 C. for 3 hr. The reaction mixture was successively washed with 5 w/v % brine (250 mL), a mixed solution of 2N hydrochloric acid/5 w/v % brine (1:1, 250 mL*2), 5 w/v % sodium bicarbonate water (250 mL) and 5 w/v % brine (250 mL). Under a nitrogen stream, magnesium sulfate (25.0 g) was added to the organic layer at 20-30 C., and the mixture was stirred at the same temperature for 30 min. Magnesium sulfate was filtered off and the residue was washed with toluene (100 mL). The filtrate was concentrated under reduced pressure to give the content (150 mL). The concentrated solution was stirred at 20-30 C., the crystals were precipitated, and heptane (750 mL) was added dropwise. The crystallized solution was heated to 40-50 C. and stirred for 30 min. After stirring, the solution was cooled to 0-10 C. and stirred at the same temperature for 2 hr. The precipitated crystals were collected by filtration, washed with toluene-heptane (1:5, 150 mL) and dried under reduced pressure at 40 C. to give 1-(4-methoxybutyl)-2-trichloromethyl-1H-benzimidazole as pale brown crystals (96.5 g, yield 82.9% from o-nitroaniline).1H-NMR (300 MHz, CDCl3) delta: 1.68-1.85 (m, 2H), 1.99-2.17 (m, 2H), 3.37 (s, 3H), 3.48 (t, J=6.1 Hz, 2H), 4.50-4.65 (m, 2H), 7.27-7.49 (m, 4H), 7.82-7.93 (m, 1H).[0086]Anal. Calcd for C13H15Cl3N2O: C, 48.55; H, 4.70; N, 8.71; Cl, 33.07. Found: C, 48.30; H, 4.61; N, 8.74; Cl, 33.30.

The synthetic route of 2533-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kitayama, Masato; US2013/90337; (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 16793-91-2 as follows. Product Details of 16793-91-2

Example 8A Di-tert-butyl (2-{5-[2-(2-chlorophenyl)ethoxy]-1-benzofur-2-yl}-2-oxoethyl)[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]malonate To a mixture of 100 mg (0.18 mmol) of the compound from Example 7A in 2.5 ml of acetonitrile were added 47 mg (0.21 mmol) of 1-(2-bromoethyl)-2-chlorobenzene and 49 mg (0.36 mmol) of potassium carbonate and the mixture was stirred under reflux for 1.5 h. Then, a further 47 mg (0.21 mmol) of 1-(2-bromoethyl)-2-chlorobenzene and 49 mg (0.36 mmol) of potassium carbonate were added and the mixture was stirred under reflux for a further 4.5 h. Then, the mixture was left to stand firstly overnight at RT and then, after another addition of 47 mg (0.21 mmol) of 1-(2-bromoethyl)-2-chlorobenzene, stirred for a further 5 h at 50 C. After cooling to RT, the mixture was admixed with 1 ml of water and purified directly by preparative HPLC (Method 7). The combined product-containing fractions were neutralized with saturated aqueous sodium hydrogencarbonate solution, concentrated to a residual volume of aqueous phase and extracted twice with dichloromethane. The combined organic phases were dried over magnesium sulphate and concentrated, and the residue was dried in vacuo. 21 mg (17% of theory, purity 100%) of the title compound were obtained. LC/MS (Method 1, ESIpos): Rt=1.59 min, m/z=702 [M+H]+.

According to the analysis of related databases, 16793-91-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BECK, Hartmut; LI, Volkhart Min-Jian; CANCHO GRANDE, Yolanda; TIMMERMAN, Andreas; BROHM, Dirk; JOeRIssEN, Hannah; BOGNER, Pamela; GERISCH, Michael; LANG, Dieter; (120 pag.)US2017/121315; (2017); 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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Chloro-4-((3-fluorobenzyl)oxy)aniline

To 2-propanol (300 niL) were sequentially added 4-chloro-5,8-dihydro-6H-spiro[l- benzothieno[2,3-d]pyrimidine-7,2′-[l,3]dioxolane] (20.7 g, 73.2 mmol), 3-Chloro-4-(3- fluoro-benzyloxy)-phenylamine (18.4 g, 73.2 mmol), and HCl in dioxane (4N, 0.92 mL). The suspension was stirred with heating to 8O0C, upon which the contents turn brown and homogeneous. After 15 h, the dark orange-yellow heterogeneous mixture was removed from heating, and allowed to cool to rt. The contents were filtered and the collected solid product dried under hi-vac. The filtrate was concentrated under reduced pressure and the residue suspended in CH3OH (50 mL), upon which formation of a second crop of product ensues. The second crop was collected, and from this filtrate a third crop could also be obtained. The solid product crops were combined to afford the final product (33.5 g, 92%) as an off-white solid. 1H-NMR (DMSO-J5) delta 1.90 (t, 2H), 3.00 (s, 2H), 3.26 (t, 2H), 3.97 (s, 4H), 5.22 (s, 2H), 7.11-7.30 (m, 4H), 7.41-7.55 (m, 2H), 7.74 (s, IH), 8.33 (s, IH), 8.39 (s, IH); LCMS RT = 3.63 min; [M+H]+ = 498.3.

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 PHARMACEUTICALS CORPORATION; ZHANG, Chengzhi; WO2006/23843; (2006); A2;,
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. 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H3BrClN3

To a solution of 5-ethylpyridin-2-amine (394 mg, 3.23 mmol) in DMF (8 mL) was added NaH (129 mg,60 % dispersion in mineral oil, 3.23 mmol) under N2 atmosphere at room temperature and stirred for another 0.5 h. To this mixture was added 8-bromo-6-chloroimidazo[l,2- b]pyridazine (0.3 g, 1.3 mmol). After 20 h stirring at room temperature, saturated NH4C1 solution was added and the reaction mixture was extracted with ether (200 mL) and washed with water (2 x 50 mL), then brine (2 x 50 mL). After drying and filtration, it was concentrated to afford 6-chloro-N-(5-ethylpyridin-2-yl)imidazo[l,2-b]pyridazin-8-amine (785 mg, crude) as a yellow solid that was used directly without further purification. LC-MS: [M + 1]+ = 274 > tR =1.726 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 933190-51-3.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; KUGLSTATTER, Andreas; LUCAS, Matthew C.; PADILLA, Fernando; WANNER, Jutta; ZHANG, Xiaohu; WO2013/64445; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 78068-85-6, name is 3-Chloro-4-fluorobenzotrifluoride, 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. COA of Formula: C7H3ClF4

To a suspension of 3,3′-dihydroxydiphenyl disulfide (1.01 g, 4.03 mmol) and Cs2CO3 (3.3 g, 10 mmol) in DMF (20 mL) was added 3-chloro-4-fluorobenzotrifluoride (2 g, 10 mmol). The reaction was heated at 100 C. overnight. The mixture was then cooled and partitioned between ether (200 mL) and water (200 mL). The aqueous layer was further extracted with ether (2¡Á100 mL). The organic layers were combined, washed with water (1¡Á100 mL), Brine (1¡Á100 mL), dried with anhydrous sodium sulfate, filtered and concentrated. The resulting oil was used in the next step directly.

The synthetic route of 3-Chloro-4-fluorobenzotrifluoride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ge, Min; He, Jiafang; Lau, Fiona Wai Yu; Liang, Gui-Bai; Lin, Songnian; Liu, Weiguo; Walsh, Shawn P.; Yang, Lihu; US2007/265332; (2007); 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. 627-42-9, name is 2-Methoxyethyl chloride, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 627-42-9

1-chloro-2-methoxyethane (0.48 mol) was added to the mixture ofmethyl 2-hydroxybenzoate (0.40 mol), K2CO3 (0.80 mol), KI(0.04 mol) and DMF (150 mL). The mixture was heated for 6 h at150 C. The solution was cooled and filtered, and the solvent wasevaporated under reduced pressure. The residue was dissolved inCHCl3 and extracted with water and 10% NaOH. The organic phasewas dried over anhydrous MgSO4 and filtered, and the solvent wasevaporated under reduced pressure. Yield: 96%, RF: 0.78 (EtOAc/petroleum ether 1:1).

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 627-42-9.

Reference:
Article; Vettorazzi, Marcela; Angelina, Emilio; Lima, Santiago; Gonec, Tomas; Otevrel, Jan; Marvanova, Pavlina; Padrtova, Tereza; Mokry, Petr; Bobal, Pavel; Acosta, Lina M.; Palma, Alirio; Cobo, Justo; Bobalova, Janette; Csollei, Jozef; Malik, Ivan; Alvarez, Sergio; Spiegel, Sarah; Jampilek, Josef; Enriz, Ricardo D.; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 461 – 481;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13918-92-8, name is 2,4-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: 13918-92-8

To a solution of 3 (10 g, 49.25 mmol) in pyridine (50 mL) wasadded benzenesulfonyl chloride 4 (64.03 mmol) slowly under icebath. After adding 4, the mixture was stirred for 18 h at room temperature.The resulting solution was quenched with iced water(500 mL), and stirred at room temperature for 1 h. The mixturewas filtered, and the precipitate was washed with water anddiethyl ether, and dried overnight to afford 5b

The synthetic route of 13918-92-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Ying; Zhang, Ling; Yang, Chao; Han, Jinsong; Wang, Chongqing; Zheng, Canhui; Zhou, Youjun; Lv, Jiaguo; Song, Yunlong; Zhu, Ju; Bioorganic and Medicinal Chemistry; vol. 24; 5; (2016); p. 957 – 966;,
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. 2845-89-8, name is 1-Chloro-3-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Chloro-3-methoxybenzene

General procedure: Under a N2 atmosphere, KOtBu (102.1 mg, 1.3 equiv) and a so-lution of complex 3a (10e50 mL, 0.01e0.05 mol%, prepared from4.6 mg of complex 3a in 1.0 mL dichloromethane) were added into aSchlenk reaction tube. The tube was sealed and the solvent wasremoved under reduced pressure. Then toluene (0.5 mL), amines(0.84 mmol) and aryl chlorides (0.70 mmol) were successivelyadded. The mixture was stirred vigorously at the specied tem-perature for 3e24 h. Then the solvent was removed under reducedpressure and the residue was puried by ash column chroma-tography (SiO2) to give the corresponding products.

According to the analysis of related databases, 2845-89-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Zhi-Mao; Gao, Yu-Jue; Lu, Jian-Mei; Tetrahedron; vol. 73; 52; (2017); p. 7308 – 7314;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 69957-83-1, 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 69957-83-1 as follows.

To a solution of N-(4-chlorobenzyl)-JV-ethylamine (0.150 g, 0.88 mmol) and {4-[(25)-2,3- diethoxy-3-oxopropyl]phenoxy}acetic acid (0.270 g, 0.91 mmol) in methylene chloride (10 mL) were added iVyV-diisopropylethylamine (0.34 mL, 1.9 mmol) and O-(benzotriazol-l-yl)- EPO tetrafluoroborate (0.320 g, 1.00 mmol) and the reaction mixture was stirred at room temperature overnight. The resulting solution was diluted with methylene chloride (40 mL) and the organic phase was washed with 5% HCl (50 mL), saturated aqueous NaHCO3 (50 mL), and brine (50 mL), dried over Na2SO4, and concentrated in vacuo. 5 Purification on a prepacked column of silica gel (Isolute SPE Column, 50 g/150 mL) with methylene chloride/ethyl acetate 10:1 as the eluent yielded 0.24 g (61%) of a colourless oil.1H NMR (500 MHz, CDCl3): delta 1.05-1.24 (m, 9H), 2.88-3.00 (m, 2H), 3.28-3.42 (m, 3H), 3.60 (m, IH), 3.96 (m, IH)3 4.12-4.20 (m, 2H), 4.56 and 4.58 (2s, 2H, rotamers), 4.64 and 4.73 (2s, 10 2H, rotamers), 6.75 and 6.88 (2d, 2H, rotamers), 7.09-7.20 (m, 4H), 7.24 and 7.30 (2d, 2H, rotamers).

According to the analysis of related databases, 69957-83-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2007/8156; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 5013-77-4, 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. 5013-77-4 name is N-Methyl-2,4-dichlorobenzylamine, 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.

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-bromo 1- (3-mtrophenyl)ethanone (2 g, 8 23 mmol, 1 00 equiv), t?ethylamme (3 4 g, 4 00 equiv), (2,4 dichlorophenyl)-N methylmethanamine (1 9 g, 10 05 mmol, 1 20 equiv), 1,4- dioxane (50 mL) The resulting solution was stirred for 2 h at room temperature at which time it was judged to be complete by LCMS The mixture was concentrated under vacuum and the residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 100-1 50) This resulted in 1 5 g (50%) of 2-((2,4- dichlorobenzyl)(methyl)ammo)-l-(3-nitrophenyl)ethanone as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-Methyl-2,4-dichlorobenzylamine, and friends who are interested can also refer to it.

Reference:
Patent; ARDELYX, INC.; CHARMOT, Dominique; JACOBS, Jeffrey, W.; LEADBETTER, Michael, Robert; NAVRE, Marc; CARRERAS, Chris; BELL, Noah; WO2010/78449; (2010); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics