Tag: M.W=100-200

Application of 433-94-3,Some common heterocyclic compound, 433-94-3, name is 2-Chloro-6-(trifluoromethyl)aniline, molecular formula is C7H5ClF3N, 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.

First, 30 g (0.153 mol) 2-chloro-6-trifluoromethylaniline (commercially available)765 ml of dimethyl sub-grind (DMSO)Followed by the addition of 68.1 g (0.23 mol) of 2-iodoheptafluoropropane,46 ml 1 molar aqueous solution of iron (II) sulfate with 15.4 g 98% strength sulfuric acid.The mixture was then degassed with argon,And using a syringe pump,Then 34.8 g of a 30% strength aqueous hydrogen peroxide solution was added dropwise over 30 minutes.During the addition,The temperature rose to 70 C.The mixture was allowed to stir for another 20 minutes,During that period,The temperature dropped to 30 C.The reaction mixture was then poured onto a saturated aqueous solution of sodium hydrogencarbonate,And extracted with ethyl acetate.The combined extracts were washed with water,Followed by washing with a saturated aqueous solution of sodium hydrogen sulfate and a saturated aqueous solution of sodium chloride,Dried over sodium sulfate,And concentrated on a rotary evaporator under reduced pressure. In terms of purification,The residue was placed in cassettes containing 330 g of silica gel,Gradient chromatography using pure cyclohexane to 90:10 (v / v) cyclohexyl acetate / ethyl acetate. This gave 46.1 g of 2-chloro-4-heptafluoroisopropyl-6-trifluoromethylaniline.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-6-(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; HALLENBACH, WERNER; SCHWARZ, HANS-GEORG; GOERGENS, ULRICH; ILG, KERSTIN; TURBERG, ANDREAS; HORSTMANN, SEBASTIAN; KOEHLER, ADELINE; (178 pag.)TW2016/7938; (2016); A;,
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Related Products of 26487-67-2, The chemical industry reduces the impact on the environment during synthesis 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, I believe this compound will play a more active role in future production and life.

0.12 g (3 mmol) of a 60percent NaH suspension in mineral oil were added under nitrogen to a solution of pyrazolo[1,5-a]pyridin-2-ylmethanol (100 mg, 0.67 mmol) in 5 mL of dry THF. The mixture was stirred for 5 h at room temperature, and after this time, was added 1-(2-chloroethyl)azepane hydrochloride (201 mg, 1.01 mmol) suspended in 8 mL of THF with 200mul of triethylamine (TEA). The mixture was heated at 55 ºC for 18 h, allowed to cool to room temperature, quenched with water and extracted with EtOAc, and washed with water. The organic layers were dried over Na2SO4 and concentrated under vacuum to afford 0.22 g (65percent) of brown oil.

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-Chloroethyl)azepane hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Laboratorios del. Dr. Esteve, S.A.; Diaz-Fernandez,Jose-Luis; Cuberes-Altisent,Mª Rosa; EP2631236; (2013); A1;,
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Application of 2106-02-7, A common heterocyclic compound, 2106-02-7, name is 2-Chloro-4-fluoroaniline, molecular formula is C6H5ClFN, 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: General procedure for synthesis of various 7-chloroquinolin-4-yl-phenylamine (1a-1p) Compounds were synthesized using 4, 7-dichloroquinoline and suitable substituted anilines. Briefly, equimolar quantities of anilines (1 mmol) and 4, 7-dichloroquinoline (1 mmol) were refluxed in dry ethanol in basic medium (1.2 mmol K2CO3) for 2-16 h depending upon the various substituents. Progress of reaction was monitored by thin layer chromatography. After completion of reaction, reaction mixture was neutralized by 1 N NaOH solution and extracted with 3 * 50 mL of CHCl3, washed with NaHCO3 and brine. The organic layer was dried over anhydrous Na2SO4. The solvent was again evaporated under reduced pressure. The ligands were purified by successive recrystallization [32].

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:
Article; Singh, Shailja; Agarwal, Drishti; Sharma, Kumkum; Sharma, Manish; Nielsen, Morten A.; Alifrangis, Michael; Singh, Ashok K.; Gupta, Rinkoo D.; Awasthi, Satish K.; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 394 – 407;,
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Adding a certain compound to certain chemical reactions, such as: 112-26-5, name is 1,2-Bis(2-chloroethoxy)ethane, 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 112-26-5, HPLC of Formula: C6H12Cl2O2

A mixture of imidazole (32 mmol, 2.176 g) and potassium hydroxide (32 mmol, 1.792 g) in DMSO (25 ml) was stirred at 70 C for 1 h. After this time, 1,2-bis(2-chloroethoxy)ethane (16 mmol, 2.48 ml) was added to the reaction mixture and stirred for 24 h. The resulting mixture was poured into 100 mL of water and extracted with methylene chloride (5 x 20 ml). The combined organic layer was washed with water (3 x 20 ml), dried with anhydrous Na2SO4, and concentrated to give 1,2-bis(2-(1H-imidazol-1-yl)ethoxy)ethane (1) as a pale yellow viscous oil, 3.10 g, 77 % yield

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:
Article; Eshghi, Hossein; Rahimizadeh, Mohammad; Hasanpour, Maede; Bakavoli, Mehdi; Research on Chemical Intermediates; vol. 41; 7; (2015); p. 4187 – 4197;,
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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. 59681-66-2, name is 4-Chloro-N1-methylbenzene-1,2-diamine, A new synthetic method of this compound is introduced below., Safety of 4-Chloro-N1-methylbenzene-1,2-diamine

General procedure: General procedure for the synthesis of 2-mercaptobenzimidazole derivatives (18-34): the proper 1,2-phenylenediamine 1-17 (16 mmol) was added over a stirred solution of ethanol (50 mL), water (5 mL), potassium hydroxide (19.2 mmol) and carbon disulfide (19.2 mmol). The mixture was heated overnight under a N2 atmosphere at 50 C. The cold reaction mixture was then neutralized with acetic acid and poured into 250 mL of cold water for complete precipitation. The solid was separated and dried using vacuum filtration. The crude product was purified by recrystallization, adding norite to the solvent.

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:
Article; Perez-Villanueva, Jaime; Hernandez-Campos, Alicia; Yepez-Mulia, Lilian; Mendez-Cuesta, Carlos; Mendez-Lucio, Oscar; Hernandez-Luis, Francisco; Castillo, Rafael; Bioorganic and Medicinal Chemistry Letters; vol. 23; 14; (2013); p. 4221 – 4224;,
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Synthetic Route of 118-69-4, A common heterocyclic compound, 118-69-4, name is 2,6-Dichlorotoluene, molecular formula is C7H6Cl2, 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.

Ammoxidation runs were carried out in a fixed bed tubular quartz reactor, which is filled with 5g of catalyst particles prepared by the methods described in examples 1 to 3 and mixed with corundum particles of the same size in 1: 1 by weight ratio. A preheating zone is provided on the top of the catalyst bed. The catalyst was activated in a mixture of air and [NH3] at [400C] for 4 hours and then the catalytic runs were performed. The 2,6-DCT and [H20] were pumped in the mole ratio of 1: 15 to 20. The product stream was collected for every half-an-hour and analysed by gas chromatography. The reaction was carried out under the following reaction conditions. A reaction temperature of 350 to [400C] was used, and the GHSV comprised between 650-750 [H-‘.] The contact time consisted of 4.8 to 5.5 seconds. The mole ratio of 2,6-DCT : H20 : NH3: air was 1: 15: 3-4: 21, the molar concentration of 2,6-DCT was 2.4 % and the ratio of O/NH3 was 1. [1 %.]

The synthetic route of 118-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TESSENDERLO CHEMIE S.A.; WO2003/101939; (2003); A2;,
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Adding a certain compound to certain chemical reactions, such as: 4090-55-5, name is 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, 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 4090-55-5, Recommanded Product: 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide

In a reflux condenser, thermometer, stirrer,Constant pressure dropping funnel 2000mL four-necked flask was added74g cyclic phosphorus oxychloride,8g anhydrous aluminum trichloride and800mL chloroform,Under stirring to make it fully dissolved.Under stirring at 10 C,22.8g of cyclohexanediamine was added to a four-necked flask,To be added after completion of cyclohexanediamine, the temperature was raised to 50 , and at this temperature for 8h,After the reaction was completed, the solvent was recovered by distillation under reduced pressure, the residue was washed with deionized water three times,A white solid powder was obtained, which was dried at 60 C for 10 h to give 72.5 g of the product in a yield of 88.8% by weight.

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; Sinopec Corporation; Sinopec Corporation Fushun Petrochemical Institute; Zhao Wei; Wang Xiaolin; Li Ming; Liu Mingrui; Xue Qian; (8 pag.)CN104558039; (2017); B;,
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Application of 626-43-7,Some common heterocyclic compound, 626-43-7, name is 3,5-Dichloroaniline, molecular formula is C6H5Cl2N, 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.

To a solution of benzoyl isothiocyanate (1.01 g, 6.17 mmol, Eq: 1.00) in acetone (15 mL), was added 3,5-dichloroaniline (1 g, 6.17 mmol, Eq: 1.00). The reaction mixture was heated at 40C for 3 hr. TLC shows starting material. The reaction was heated to 50C overnight. The reaction was cooled to room temperature, and carefully poured into ice water (pH 5). The resulting sold was filtered, washed with water, and dried to give 1.85 g (92%) of desired product as an off- white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dichloroaniline, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DING, Qingjie; JIANG, Nan; WEIKERT, Robert James; WO2014/135472; (2014); A1;,
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Some common heterocyclic compound, 4090-55-5, name is 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, molecular formula is C5H10ClO3P, 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. Recommanded Product: 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide

(2R,3R,4R, 5R)-5 -((((((2R,3R,4R, 5R)-5-(6-Benzamido-9H-purin-9-yl)-4-((tert- butyldimethylsilyl)oxy)-2-(hydroxymethyl)tetrahydrofuran-3 -yl)oxy)(2-cyanoethoxy)phosphoryl)oxy)methyl)-4-((tert-butyldimethylsilyl)oxy)-2-(4-oxo-4, 5 -dihydro1 H-imidazo [4,5 -c]pyridin- 1 -yl)tetrahydrofuran-3 -yl hydrogen phosphonate (160 mg) was subjected to azeotropic dehydration with anhydrous pyridine, and anhydrous pyridine (3.0 mL) was added thereto. To the mixture was added 2-chloro-5,5-dimethyl-1,3,2- dioxaphosphinane 2-oxide (99 mg) at room temperature, and the mixture was stirred at room temperature for 1 hr. Water (96 1iL) and iodine (50.5 mg) were added thereto, and the mixture was stirred at room temperature for additional 20 mm. To the reaction mixture was added a mixture of sodium thiosulfate (190 mg) and water (0.4 mL), and the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (10.6 mg). MS: [M+H] 1044.3

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4090-55-5, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; YOSHIKAWA, Masato; SAITOH, Morihisa; KATO, Taisuke; YOSHITOMI, Yayoi; SEKI, Tomohiro; NAKAGAWA, Yasuo; TOMINARI, Yusuke; SETO, Masaki; SASAKI, Yusuke; OKANIWA, Masanori; ODA, Tsuneo; SHIBUYA, Akito; HIDAKA, Kosuke; SHIOKAWA, Zenyu; MURATA, Shumpei; OKABE, Atsutoshi; NAKADA, Yoshihisa; MOCHIZUKI, Michiyo; FREEZE, Brian Scott; TAWARAISHI, Taisuke; WADA, Yasufumi; GREENSPAN, Paul D.; (423 pag.)WO2018/100558; (2018); A2;,
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Related Products of 261762-56-5, 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 261762-56-5 as follows.

Example 12 5-{[1-(4-Chloro-3-fluoro-2-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-(methoxymethyl)propyl]amino}-7-fluoro-1H-quinolin-2-one; (4-chloro-3-fluoro-2-methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methanone1 g (6.2 mmol) 3-Chloro-2-fluoroanisole in 10 ml THF are cooled to -70 C. and 2.7 ml of a 2.5 M n-butyl lithium solution in hexane are added. After 1.5 hours at -70 1 g (6.9 mmol) N,N’-dimethoxy-N,N’-dimethyl urea in 6 ml THF are added at -70 C. and the mixture is stirred another hour at -70 C. 7.5 ml of a 2 M aqueous HCl are added and the reaction is warmed to ambient temperature over 18 hours. The reaction mixture is partitioned between diethyl ether and water. The aqueous phase is extracted with diethyl ether, the combined organic phases are washed with brine, dried over sodium sulfate and evaporated. The crude product is purified by chromatography on silica gel (ethyl acetate in hexane 0 to 30%) to yield 0.59 g 4-chloro-3-fluoro-2,N-dimethoxy-N-methylbenzamid. 1H-NMR (CDCl3); delta=3.35 (br, 3H), 3.49 (br, 3H), 3.98 (s, 3H), 6.99 (dd, 1H), 7.13 (dd, 1H).0.44 ml (5.1 mmol) 1,1,1-trifluoro-2,3-epoxypropane in 7.5 ml THF and 2.2 ml hexane are cooled to -100 C. and 2.03 ml of a 2.5 M n-butyl lithium solution (5.1 mmol) in hexane are added over 15 minutes while the temperature does not exceed -95 C. 10 minutes after complete addition 0.57 g (2.3 mmol) 4-chloro-3-fluoro-2,N-dimethoxy-N-methylbenzamid in 10 ml THF are added over 15 minutes while the temperature does not exceed -95 C. After 3 hours at -100 C. 2.3 ml diethyl ether is added and the reaction mixture is warmed to room temperature over 14 hours. The reaction is quenched by addition of saturated ammonium chloride solution. The phases were separated and the aqueous layer is extracted twice with diethyl ether, the combined organic phases washed with brine, dried over sodium sulphate and then evaporated to yield 570 mg of (4-chloro-3-fluoro-2-methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methanone. 1H-NMR (CDCl3); delta=2.99 (dq, 1H), 3.37 (d, 1H), 4.14 (d, 3H), 7.18 (m, 1H), 7.19 (m, 1H). 285 mg (0.95 mmol) (4-Chloro-3-fluoro-2-methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methanone are stirred with 622 mg (1.9 mmol) caesium carbonate in 6.7 ml methanol. The reaction is quenched by addition of water after one day. The aqueous layer is extracted with ethyl acetate, the combined organic phases are washed with brine, dried over sodium sulphate and then evaporated to yield 262 mg 1-(4-chloro-3-fluoro-2-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-methoxymethypropan-1-one. To 27 mg (0.15 mmol) 5-Amino-7-fluoro-1H-quinolin-2-one and 50 mg (0.15 mmol) 1-(4-chloro-3-fluoro-2-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-methoxymethypropan-1-one in 0.45 ml toluene and 0.13 ml 1,4-dioxane are added 33 mul acetic acid and 0.12 ml tetra butyl orthotitanate. The mixture is heated over 20 hours to 110 C., cooled to room temperature and poured into aqueous ammonium fluoride solution. Ethyl acetate is added and the mixture is stirred vigorously for 30 minutes. Phases are separated and two times extracted with ethyl acetate. The combined organic phases are concentrated to yield quantitatively 5-{[1-(4-chloro-3-fluoro-2-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-methoxymethylpropylidene]amino}-7-fluoro-1H-quinolin-2-one. The raw imine in 4.2 ml methanol is cooled to 5 C. and 120 mg sodium boron hydride are added in multiple portions over the period of 72 hours. The reaction is quenched by addition of saturated ammonium chloride solution and diluted with water and ethyl acetate. The phases are separated, the aqueous layer is extracted with ethyl acetate, the combined organic phases are washed with brine and dried over sodium sulphate. After removal of the solvent preparative thin layer chromatography on silica gel (acetone in methylene chloride, 30%) yields 9.5 mg of the title compound.1H-NMR (CD3OD); delta=3.44 (s, 3H), 3.65 (m, 1H), 3.69 (d, 1H), 4.05 (d, 3H), 5.44 (s, 1H), 6.03 (dd, 1H), 6.30 (dd, 1H), 6.45 (d, 1H), 7.12 (dd, 1H), 7.35 (dd, 1H), 7.94 (d, 1H).

According to the analysis of related databases, 261762-56-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Berger, Markus; Rehwinkel, Hartmut; Zollner, Thomas; May, Ekkehard; Hassfeld, Jorna; Schacke, Heike; US2009/137564; (2009); A1;,
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