Month: March 2021

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 1303587-99-6 as follows. Safety of 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine

Synthesis of2-chloro-8-(4-(trifluoromethoxy) benzyl)-7, 8-dihydro-6H-pyrimido [5, 4-b] [I, 4] oxazine [0456] To a stirred solution of 2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (150 mg, 0.87 mmol) in DMF (5 mL) under argon atmosphere were added sodium hydride (42 mg, 1.75 mmol) and l-(bromomethyl)-4-(trifluoromethoxy) benzene (268 mg, 1.05 mmol) at 0C. The reaction mixture was warmed to RT and stirred for 1 h. After consumption of the starting materials (monitored by TLC), the reaction was diluted with water (20 mL) and extracted with EtOAc (2 x 20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography using 40% EtOAc:hexane to afford 2-chloro-8-(4- (trifluoromethoxy) benzyl)-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (160 mg, 53%>) as an off-white solid. 1H-NMR (DMSO-<, 400 MHz): delta 7.71 (s, 1H), 7.42 (d, 2H), 7.34 (d, 2H), 4.80 (s, 2H), 4.21-4.19 (m, 2H), 3.52-3.50 (m, 2H); LCMS: 345.8 (M+); (column; X- Select CSH C-18 (50 3.0 mm, 3.5 mupiiota); RT 3.94 min 0.05% Aq TFA: ACN; 0.80 mL/min); TLC: 60% EtOAc/hexane (R 0.6). According to the analysis of related databases, 1303587-99-6, the application of this compound in the production field has become more and more popular. Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, 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 4584-46-7, Product Details of 4584-46-7

To a solution of 4-hydroxy-3-methoxybenzaldehyde (10g) in DMF (500ml) were added potassium carbonate (18.20g)and 2-chloro-N,N-dimethylethylamine hydrochloride (14.08g). The reaction mixture was stirred at 80C for 1 h30min. The suspension was filtrated off and the filtrate was diluted with Et20 and sat. aq. NaCI. The aq. layer was extracted with Et20, the combined org. layers were dried over MgS04, filtrated off and evaporated in vacuo. The crude was purified by CC (Buchi Sepacore, 70g cartridge, solvent A: DCM, solvent B: MeOH, gradient in %B: 2 to 4, flow rate: 20ml/min) to afford 7.3g of a yellow oil. LC-MS (A): tR = 0.60min; [M+H]+: 224.48.

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; ACTELION PHARMACEUTICALS LTD; BUR, Daniel; GRISOSTOMI, Corinna; KIMMERLIN, Thierry; REMEN, Lubos; SIENDT, Herve; VERCAUTEREN, Magali; WELFORD, Richard; (138 pag.)WO2016/177690; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 4090-55-5, name is 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, 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. Safety of 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide

General procedure: Ph(But)P(O)Cl or 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide (5.0mmol) was added to the suspension of NaH (0.133g, 5.5mmol) in THF (25mL). Subsequently, 5,7-dibromo-2-methylquinolin-8-ol (1a), 5-fluoro-2-methylquinolin-8-ol (1i) (5.0mmol) in THF (5mL), was added. The reaction was carried out for 24 h under reflux. The mixture was allowed to cool to room temperature. The reaction was neutralized with aqueous solution of KHSO4. After extraction with CH2Cl2 (3¡Á50mL), the organic phase was dried over MgSO4, followed by filtration and solvent evaporation. The crude product was purified by chromatography and crystallization.

The synthetic route of 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nycz, Jacek E.; Szala, Marcin; Malecki, Grzegorz J.; Nowak, Maria; Kusz, Joachim; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 117; (2014); p. 351 – 359;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 6781-98-2, name is 2-Chloro-1,3-dimethylbenzene, molecular formula is C8H9Cl, 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. Product Details of 6781-98-2

General procedure: To a 50 mL Schlenk tube containing base (1.5 mmol) and precatalyst 4a (1 mol %, 0.0083 g) purged with N2 (three times), amine (1.2 mmol) was added via syringe, and the resulted mixture was allowed to stir at room temperature for 2-3 min. Solvent (1 mL) was then injected via syringe followed by the aryl chloride (1.0 mmol). If the aryl chloride was a solid, it was introduced into the vial prior to purging with N2. At this time, the reaction was stirred for 24 h at 100 C. After cooling to the room temperature, the reaction mixture was concentrated in vacuo and directly purified via silica gel flash chromatography. N-(2,6-Dimethylphenyl)-2,4,6-trimethylaniline (26) ;1H NMR (CDCl3, 400 MHz, 298 K): delta=6.97 (d, J=7.6 Hz, 2H), 6.81-6.78 (m, 3H), 4.71 (br s, 1H), 2.25 (s, 3H), 1.99-1.95 (m, 12H); 13C NMR (CDCl3, 100 MHz, 298 K): delta=142.14, 138.94, 131.43, 130.40, 129.17, 128.74, 128.34, 120.91, 20.55, 19.06, 18.96; GC-MS: tR=16.270 min, m/z=239.1 [M]+, 239.1, 222.1, 208.1, 132.0, 120.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6781-98-2, its application will become more common.

Reference:
Article; Fang, Weiwei; Jiang, Jian; Xu, Yong; Zhou, Juefei; Tu, Tao; Tetrahedron; vol. 69; 2; (2013); p. 673 – 679;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2106-04-9, 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. 2106-04-9 name is 3-Chloro-2-fluoroaniline, 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.

General procedure: To a solution of (E)-N-(2-cyano-4-nitrophenyl)-N,N-dimethylformimidamide 17 (6.0 g, 2.7 mmol) and acetic acid (45 mL) was added 3-fluoroaniline (18a, 3.3 g, 3.0 mmol) at room temperature. The reaction mixture was heated up to reflux temperature for 1 h. After completion of the reaction, the resulting mixture was cooled to room temperature. The solid separated was filtered and washed with ether to give 19a, 6.5 g (83%);

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-2-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Article; Marvania, Bhavin; Lee, Pei-Chih; Chaniyara, Ravi; Dong, Huajin; Suman, Sharda; Kakadiya, Rajesh; Chou, Ting-Chao; Lee, Te-Chang; Shah, Anamik; Su, Tsann-Long; Bioorganic and Medicinal Chemistry; vol. 19; 6; (2011); p. 1987 – 1998;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 2845-89-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2845-89-8, name is 1-Chloro-3-methoxybenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A Schlenk ask was charged with the required aryl chloride (0.25 mmol), amine (0.30 mmol), N-heterocyclic carbene-palladium(II) complex (2 mol%), KOtBu (1.3 equiv), and toluene (0.5 mL). The mixture was stirred at 110 C for 15 h under N2. After cooling, the mixture was evaporated and the product was isolated by preparative TLC on silica gel plates. The puried products were identied by 1H NMR spectra, and their analytical data are given in the Supporting Information.

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-Chloro-3-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Tao; Xu, Kai; Liu, Lantao; Xie, Huanping; Li, Ying; Zhao, Wen-Xian; Transition Metal Chemistry; vol. 41; 5; (2016); p. 525 – 529;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 104-11-0, These common heterocyclic compound, 104-11-0, name is 1-(4-Chlorophenyl)-N-methylmethanamine, 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.

EXAMPLE 10 1-(N-4-Chlorobenzyl-N-methyl-amino)-3-methyl-4-isoquinoline Acetic Acid Hydrochloride N-Methyl-4-chlorobenzylamine (1.40 g., 9.0 mmol) and 1-chloro-3-methyl-4-isoquinoline acetic acid (770 mg., 3.0 mmol), prepared as in Example 8, were refluxed in 20 ml. p-dioxane for 16 hr. The cooled reaction mixture was partitioned between 200 ml ether and 50 ml 1 N sodium hydroxide. The ether rafinate was extracted with 2*30 ml 1 N sodium hydroxide. The combined basic phases were acidified to pH 6.5 with 6 N hydrochloric acid and extracted with 3*75 ml ethyl acetate. This organic phase was dried over magnesium sulfate, filtered, and vacuum evaporated to an oily residue. Chromatography of this on silica gel eluted with ethyl acetate gave an oil. The title compound was prepared from this oil by treatment with hydrochloric acid gas in ether, filtrate, and drying in vacuo; 52 mg. (4%), m/e 354.

Statistics shows that 1-(4-Chlorophenyl)-N-methylmethanamine is playing an increasingly important role. we look forward to future research findings about 104-11-0.

Reference:
Patent; Pfizer Inc.; US4283539; (1981); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 1939-99-7, name is Phenylmethanesulfonyl 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. name: Phenylmethanesulfonyl chloride

Synthesis of Ethyl 1-(benzylsulfonyl)piperidine-2-carboxylate (Ref .1 ) Ethyl piperidine-2-carboxylate (100mg, 0.63 mmol) was dissolved in 5mL of anhydrous DMF, and triethylamine (191mg, 1.89 mmol) was added drop wise followed by phenylmethanesulfonyl chloride (119.7mg, 0.63 mmol). The reaction was stirred for 6h at RT and subsequently the solvent was removed in vacuo. The crude mixture was purified using column chromatography (hexane : EtOAc 8:2) to yield Ethyl 1-(benzylsulfonyl)piperidine-2-carboxylate_(170mg, 0.55 mmol, 86%). TLC (hexane: EtOAc 8:2): Rf = 0.20. HPLC (gradient A) retention time= 23.4-23.8 min 1 HNMR (300 MHz, CDCI3) delta= 1 .14-1 .25 (m, 1 H), 1 .28 (t, 3H, J= 7.2 Hz), 1 .34-1 .49 (m, 1 H), 1 .54-1 .68 (m, 3H), 2.14 (d, 1 H, J= 13.5 Hz), 3.14 (dt, 1 H, J= 3.3, 12.6 Hz), 3.44 (d, 1 H, J= 12.6 Hz), 4.18-4.24 (m, 2H), 4.26 (s, 2H), 4.54 (d, 1 H, J= 4.8 Hz), 7.31 -7.38 (m, 3H), 7.43-7.48 (m, 2H). 13C NMR (75 MHz, CDCI3) delta= 14.22, 20.31 , 25.04, 27.78, 43.39, 55.95, 58.71 , 61 .36, 128.40, 128.48, 129.35, 130.96, 171 .38. MS (ESI) m/z: found Rt 14.28 min. (Method LCMS), 312.12 [M + H] +, 334.22 [M + Na] +. calculated 312.12 [M + H] +, 334.1 1 [M + Na] +.

The synthetic route of Phenylmethanesulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MAX-PLANCK-GESELLSCHAFT ZUR FOeRDERUNG DER WISSENSCHAFTEN E.V.; GOPALAKRISHNAN, Ranganath; HAUSCH, Felix; WO2013/97947; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 56961-77-4,Some common heterocyclic compound, 56961-77-4, name is 1-Bromo-2,3-dichlorobenzene, molecular formula is C6H3BrCl2, 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.

Under a nitrogen atmosphere, and added at 120 will have the N 1 , the N 1 ,the N 3 – triphenyl benzene-1,3-diamine (20.0g), 1- bromo-2,3-dichlorobenzene ( 6.4g),Pd-132 (0.2g ), NaOtBu (6.8g) and xylene (70ml) was stirred for 2 hours the flask washeated. The reaction mixture was cooled until room temperature, water and ethyl acetateto carry out a liquid. Then, the use of silica gel column chromatography (eluent:toluene / heptane = 4/6 (volume ratio)) to be purified, to thereby obtain the N 1 , theN 1 ‘ – (2- chloro-1,3-phenylene yl) bis (the N 1 , the N 3 , the N 3 – phenyl-trityl-1,3-diamine) (15.0g)

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

Reference:
Patent; Kwansei Gakuin School Corporation; Tian, Shanzuoci; Zhong, Zhongzongyiliang; Zhong, Daoguiyi; Ping, Jingdagui; Xiao, Yeyangping; Zhi, Lianyizhi; Ni, Jingping; Song, Xiawusi; Sheng, Tianlizhao; (405 pag.)CN105431439; (2016); A;,
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

Step 1: In a sealed tube 4-chloro-2-anisidine (3.0 g, 19.0 mmol), 5-chloro-2-trifluromethylpyridine (3.8 g, 20.9 mmol) and Cs2C03 (8.02 g, 24.7 mmol) were mixed in toluene (50 mL). The resulting mixture was purged with nitrogen, added Pd(OAc)2 (0.64 g, 2.8 mmol) and X-phos (0.45 g, 0.95 mmol) and heated at 140 C for 12 h. After completion of the reaction, the reaction mixture was filtered through Celite bed and concentrated under vacuum. The residue obtained was diluted with ethyl acetate (200 mL), washed with water, brine solution and dried over anhydrous Na2S04. The organic phase was concentrated and purified by the column chromatography (230-400 size mesh) to get the desired product /V-(4-chloro-2-methoxyphenyl)-6- (trifluoromethyl)pyridin-3-amine (3.5 g, 61.4%). LC MS: 303.0 (M+H), RT- 3.45 min, 96.03% (max) Method A-0.1% HCOOH; B-ACN Flow = 1.5 mU in. Column-ZORBAX XDB C18 (50X 4.6mm-5pm) positive Mode 1H NMR (300 MHz, DMSO-d6) : delta 8.42 (s, 1H), 8.27 (d, J = 2.58 Hz, 1H), 7.58 (d, J = 8.7 Hz, 1H), 7.21-7.27 (m, 2H), 7.16 (d, J = 2.16 Hz, 1H), 6.97 (dd, J = 2.17, 9.80 Hz, 1 H), 3.81 (s, 3H).

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 93-50-5.

Reference:
Patent; MERCK PATENT GMBH; SPANGENBERG, Thomas; (129 pag.)WO2016/827; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics