Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 220227-21-4, name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride, 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 220227-21-4, Formula: C6H2ClF3O2S

A mixture of 2,4,5-trifluorobenzene-1-sulfonyl chloride (5.00 g, 21.7 mmol), 2,4- dimethoxybenzylamine (3.63 g, 21.7 mmol), diethylpropylethylamine (3.36 g, 26.0 mmol) in dichloromethane (100 mL) was stirred at ambient temperature for 16 h. The mixture was diluted in dichloromethane (100 mL), washed with iN hydrochloric acid, 25% aqueous ammonium chloride and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was crystallized from dichloromethane/hexanes to obtain N-(2,4-dimethoxybenzyl)-2,4,5- trifluorobenzenesulfonamide as a cream solid in 95% yield (7.5 g): 1H NMR (300 MHz, CDCI3) delta 7.55-7.47 (m, 1H), 6.81-6.76 (m, 2H), 6.25-6.20 (m, 2H), 5.50 (s, 1H), 4.18 (5, 2H), 3.76-3.73 (m, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4,5-Trifluorobenzene-1-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; XENON PHARMACEUTICALS INC.; SUN, Shaoyi; ZENOVA, Alla, Yurevna; CHAFEEV, Mikhail; JIA, Qi; ZHANG, Zaihui; OBALLA, Renata, Marcella; WO2013/64983; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 19230-27-4,Some common heterocyclic compound, 19230-27-4, name is 1,3-Dibromo-2-chlorobenzene, molecular formula is C6H3Br2Cl, 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 suspension of I ,3 dibromo2chorobenzene (300 mg, 1.11 mmo), 4methoxypiperidine (168 mg, 1.11mmo), sodium tert-butoxide (160 mg, 167 mmo) in touene (30 m), was added BNAP (35 mg, 005 mrnofl and Pd2(dba)3 (20 mg, 002 mmo) at once. The mixture was degassed with nitrogen for 10 minutes and then heated at 140 C for I h in microwave. After coohng to rt, the reaction mixture was diuted with water and extracted with EtOAc(x 3). The combined organic extracts were dried (Na2SO4), fi[tered and concentrated. Purification (FCC, Si02 0 -. 100% EtOAc/hexanes) afforded the tWe compound as a oH (168 mg, 50% yied). MS (ES): mass cacd. for C12H15BrCNO, 304.6; mfz found, 305.6 [M+HJ. 1H NMR (400 MHz, DMSO): oe 742 (dd, J= 7.7, 1.7 Hz, IH), 7.28-7.14 (m, 2H), 3.39-3.33 (m, IH), 3.28 (s, 3H), 3.14(dt, J= 10.5, 4.5 Hz, 2H), 277 (ddd, J=12.0, 9.2, 3.0 Hz, 2H), 2.04- 1.91 (m, 2H), 1.61 (dtd, J= 12.2, 8.8, 3.4 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dibromo-2-chlorobenzene, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; RAVULA, Suchitra; SWANSON, Devin M.; SAVALL, Bradley M.; AMERIKS, Michael K.; (250 pag.)WO2016/176449; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 14862-52-3, name is 3,5-Dibromochlorobenzene, 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 14862-52-3, Safety of 3,5-Dibromochlorobenzene

3-cyanophenyl boronic acid (25.0 g, 0.17 mol) and 1,3-dibromo-5-chlorobenzene (23.0 g, 0.08 mol) Dissolved in 290 mL of tetrahydrofuran, 1.5 M aqueous potassium carbonate solution (90 mL) was added,Tetrakis- (triphenylphosphine) palladium (3.94 g, 0.34 mmol) was added thereto, followed by heating with stirring for 13 hours.The temperature was lowered to room temperature, the water layer was separated off, dried over anhydrous magnesium sulfate and concentrated under reduced pressureRecrystallization was performed using chloroform and ethanolWas dried to prepare the intermediate n (44.7 g, yield 83%).

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

Reference:
Patent; LG Chem, Ltd.; Lee Jeong-ha; Moon Jeong-uk; Jeong Min-u; Lee Dong-hun; Chae Mi-yeong; (49 pag.)KR2018/32517; (2018); A;,
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. 367-22-6, name is 4-Chloro-3-fluoroaniline, A new synthetic method of this compound is introduced below., Formula: C6H5ClFN

To a solution of 4-chloro-3-fluoroaniline (15 g, 103.05 mmol) in dichloromethane (150 mL) was added ICl (25 g, 154.57 mmol) drop wise. The resulting black mixture was stirred at 24-29C for 2h. The mixture was diluted with 100 mL dichloromethane and washed with saturated solution of sodium bicarbonate (200 mL). The organic layer was concentrated to give the crude residue, which was purified by flash column chromatography on silica gel (0 to 0.5%ethyl acetate in Petroleum ether) to afford compound 41a (8 g brown solid and 12 g black solid, 71.5% yield in total). LCMS: R t = 0.974 min in 5-95AB_220&254 chromatography (MERCK RP18 2.5-2mm), MS (ESI) m/z = 271.8 [M+H] +. 1H NMR: (400MHz, CDCl 3) delta 7.53 (d, J = 8.0 Hz, 1H), 6.46 (d, J = 10.4 Hz, 1H), 4.12 (s, 2H).

The synthetic route of 367-22-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD; LI, Zhengtao; ZOU, Hao; ZHU, Wei; SHEN, Changmao; WANG, Rumin; LIU, Wengeng; CHEN, Xiang; TSUI, Honchung; YANG, Zhenfan; ZHANG, Xiaolin; (307 pag.)WO2019/149164; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 13078-79-0, 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. 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, This compound has unique chemical properties. The synthetic route is as follows.

Triethylamine (153 muL, 1.10 mmol) was added dropwise at 0 C to a stirred suspension of 2-(1H-indol-3-yl)-2-oxoacetyl chloride (5; 208 mg, 1.00 mmol) and 2-(3-chlorophenyl)ethylamine (139 muL, 1.00 mmol) in anhydrous tert-butyl methyl ether (20 mL). The reaction mixture was stirred at 0 C for 15 min and then for 1 h at room temperature, monitoring the reaction by TLC analysis. After completion of the reaction the mixture was washed with a saturated NaHCO3 aqueous solution and water (3 × 20 mL in each case). The organic layer was dried over anhydrous Na2SO4 and evaporated. Recrystallization of the crude product from ethanol 70% yielded colourless crystals (33%).Mp.: 184-186 C; IR (KBr): 3347 cm-1 and 3190 cm-1 (NH), 2938 cm-1 (CH aliph.), 1657 cm-1 (CO); 1H NMR (DMSO-d6, 400.1 MHz): delta (ppm) = 2.88 (t, 2H, J = 7.0 Hz, NHCH2CH2), 3.50 (dt, 2H, J = 6.4/6.8 Hz, NHCH2CH2), 7.21-7.34 (m, 6H, ar-H), 7.52-7.57 (m, 1H, ar-H), 8.21-8.27 (m, 1H, ar-H), 8.67 (s, 1H, ar-H), 8.81 (t, 1H, J = 5.8 Hz, NH), 12.24 (s, 1H, indole-NH); 13C NMR (DMSO-d6, 100.6 MHz): delta (ppm) = 34.2 (CH2), 39.2 (CH2); 112.5, 121.2, 122.5, 123.4, 126.1, 127.5, 128.5, 130.1, 138.4 (tert. C); 112.1, 132.9, 136.3, 141.9, 163.6, 182.1 (quat. C, one signal is missing due to peak overlap); C18H15ClN2O2 (326.78); calcd. C 66.16, H 4.63, N 8.57; found C 65.84, H 4.60, N 8.31; HPLC-purity: 99.3% at 254 nm and 98.9% at 280 nm, tN = 3.38 min, tM = 1.03 min (ACN/H2O; 55:45), lambdamax: 256 nm and 327 nm.

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; Schmidt, Stefanie; Preu, Lutz; Lemcke, Thomas; Totzke, Frank; Schaechtele, Christoph; Kubbutat, Michael H.G.; Kunick, Conrad; European Journal of Medicinal Chemistry; vol. 46; 7; (2011); p. 2759 – 2769;,
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. 50638-46-5, name is 4-Bromo-3-chloroanisole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-Bromo-3-chloroanisole

A mixture of 1 -bromo-2-chloro-4-methoxybenzene (1.5 g, 6.8 mmol), oxazole (878 mg, 12.7 mmol), /-BuOK (1.52 g, 13.5 mmol) and tetrakis (1.56 g, 1.35 mmol) in dioxane (10 mL) was heated to 100C under N2 atmosphere for 4 hr. After cooling to r.t., the reaction mixture was concentrated under reduced pressure to give the crude product which was purified by flash chromatography (silica gel, 0 to 25% EA in PE) to afford 2-(2-chloro-4-methoxyphenyl)oxazole (40) (600 mg, 42 % yield) as a yellow solid. LC-MS (ESI): mlz (M+l) 210.0.

According to the analysis of related databases, 50638-46-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACYCLICS LLC; CHEN, Wei; WANG, Longcheng; YAN, Shunqi; LOURY, David, J.; JIA, Zhaozhong, J.; FRYE, Leah, Lynn; GREENWOOD, Jeremy, Robert; SHELLEY, Mee, Yoo; ATALLAH, Gordana, Babic; ZANALETTI, Riccardo; CATALANI, Maria, Pia; RAVEGLIA, Luca, Francesco; (402 pag.)WO2016/4272; (2016); 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. 93-50-5, name is 4-Chloro-2-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Chloro-2-methoxyaniline

Example 57; 4-(4-Chloro-2-methoxy-phenyl)-3-(4-ethoxy-phenyl)-5-methyl-4H-[1,2,4]triazole; The products of preparations 4 (1g, 4. 9mmol) and 91 (926mg, 5. 88mmol) were dissolved in xylene (20ml) and the reaction mixture was heated for 10 hours at 150C. Heating was continued for 4.5 hours with portions of para-toluenesulfonic acid (100mg) added to the mixture at regular intervals until tic analysis showed all of the starting material to be consumed. The reaction mixture was then taken up into 2N hydrochloric acid and ethyl acetate and partitioned. The aqueous layer was basified with sodium hydroxide pellets and re-extracted with ethyl acetate. The combined organic phase was dried over sodium sulfate and evaporated to give a dark brown oil. Trituration with diethyl ether formed a dark brown solid that was re-crystallised from ethyl acetate to produce the title compound as a beige solid (340mg). Evaporation of the ethyl acetate gave a further residue that was purified by column chromatography on silica gel, eluting with dichloromethane : methanol : 0.88 ammonia, 98.2 : 0.2, to afford further amounts of product giving a total yield of 37% (629mg). ‘H NMR (CDCI3, 400MHz) d : 1.39 (t, 3H), 2.27 (s, 3H), 3.73 (s, 3H), 3.99 (q, 2H), 6.78 (d, 2H), 7.02-7. 06 (m, 3H), 7.31 (d, 2H). MS APCI+ m/z 344 [MH] +

According to the analysis of related databases, 93-50-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/82866; (2005); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 210532-25-5, 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. 210532-25-5 name is 3,5-Difluorobenzene-1-sulfonyl 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.

1.132 g (5.32 mmol) of 3,5-difluorobenzene-1-sulfonyle chloride is added under argon to a solution of 545 mg (3.55 mmol) of 5-amino-2-chloronicotinotrile in 20 mL of an anhydrous 1:1 mixture of THF and pyridine. The reaction medium is heated to 70C for 3 hours and let 12 additional hours under stirring at room temperature. The solvent is dry evaporated and the crude reaction product is redissolved in ethyl acetate and washed with several aqueous fractions. The organic phase is dried on magnesium sulfate, filtered, concentrated and then purified by silica gel chromatography to yield 784 mg (67%) of N-(6-chloro-5-cyanopyridin-3-yl)-3,5-difluorobenzene-sulfonamide. 1H NMR: deltaH ppm (400 MHz, DMSO) : 11,39 (1H, sl, NH), 8. 34 (1H, m, CHarom), 8,10 (1H, m, CHarom), 7,67 (1H, m, CHarom), 7,59 (2H, m, CHarom).

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

Reference:
Patent; PIERRE FABRE MEDICAMENT; Sokoloff, Pierre; Cachoux, Frederic; EP2689778; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 19393-92-1, 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 19393-92-1 as follows.

EXAMPLE 263 (+-)-{[5-chloro-7-(2,6-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine The title compound was prepared (0.072 g, 8percent) following the general procedure of Example 166 as a white solid, hydrochloride salt from (5-chloro-2-methoxyphenyl)boronic acid (5.0 g, 26.88 mmol) and 2-bromo-1,3-dichlorobenzene (12.14 g, 53.76 mmol). mp 234-236° C.

According to the analysis of related databases, 19393-92-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2005/261347; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2687-12-9,Some common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, molecular formula is C9H9Cl, 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: Distilled H2O in a three-necked roundbottom flask ispurged with nitrogen for 30 minutes. PdCl2 and KCl aresubsequently added to the flask and the solution is stirred atroom temperature for 1 h. Then, optionally substituted(R4)-allyl chloride is added and the resulting reactionmixture is stirred at room temperature overnight (18-20 irs).The reaction is extracted with chloroform, and the aqueouslayer washed with chloroform three times. The organiclayers are combined, dried over MgSO4, filtered and concentrated in vacuo. The crude product is recrystallised fromchloroform and methyl tert-butyl ether, and the resultingsolid is isolated by filtration and dried in vacuo; PdCl2 (590 mg, 3.33 mmol); KCl (473 mg, 6.67 mmol); cinnamyl chloride (1.39 mL, 9.99 mmol); H2O (83 mL). Thedimer is obtained as a yellow solid.

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

Reference:
Patent; Johnson Matthey Public Limited Company; Colacot, Thomas; Jon Deangelis, Andrew; (66 pag.)US9777030; (2017); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics