Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 90390-33-3, name is 3-Chloro-5-fluorobenzylamine, 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 90390-33-3, 90390-33-3

A solution of compound ethyl 2-oxopyrrolidine-3-carboxylate (180.00 g, 929.61 mmol) and (3-chloro-5-fluorophenyl) methanamine (148.36 g, 929.61 mmol) in xylene (4.00 L) is heated to 130 C for 16 hours. LCMS showed the starting material is still present. The reaction mixture is cooled to 10 C and a solid precipitates out after 30 minutes. The suspension is filtered and the filter cake is washed with xylene (3 x500 mL), petroleum ether (2×500 mL), and dried under vacuum to give the desired product (81 g). The filtrates are concentrated under reduced pressure and the residue in xylene (3 L) is heated to 130 C for 40 hours. The reaction mixture is cooled to 10 C and the solid precipitates out after 30 minutes. The suspension is filtered and the filter cake is washed with xylene (2×500 mL), petroleum ether (2×500 mL) and dried in vacuum to give the title product (81.38 g) which is combined with the first lot to give a title product (164.38 g, 607.26 mmol, 65.32% yield) as a white solid. ES/MS m/z 270.9 (M+l).

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-5-fluorobenzylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD; HO, Koc Kan; QUAN, Weiguo; ZHOU, Jingye; (51 pag.)WO2018/102256; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2106-04-9, Adding some certain compound to certain chemical reactions, such as: 2106-04-9, name is 3-Chloro-2-fluoroaniline, 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 2106-04-9.

Example 40 7-[2-Amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-N-(3-chloro-2-fluorophenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide To a solution of 20% phosgene in toluene (phosgene:toluene=1:4, 54.9 uL, 0.104 mmol) was added a solution of 3-chloro-2-fluoroaniline (6.5 mg, 0.045 mmol) (Aldrich, Cat. #530174) and triethylamine (19.3 uL, 0.138 mmol) in THF (0.4 mL). The resulting mixture was stirred at r.t. for 2 h., and concentrated. To the residue was added a solution of 4-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt (15 mg, 0.034 mmol) and triethylamine (19.3 uL, 0.138 mmol) in acetonitrile (0.4 mL). The reaction mixture was stirred at r.t. for 30 min The mixture was purified by RP-LCMS (pH=10) to afford the desired product. Analytic LCMS (M+H)+: m/z=496.1/498.1.

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 2106-04-9.

Reference:
Patent; INCYTE CORPORATION; US2010/240671; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

72934-36-2, 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. 72934-36-2 name is 1-(4-Chlorophenyl)cyclopropanamine, 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.

To a slurry of tert-butyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (3.6 g) and 1-(4-chlorophenyl)cyclopropanamine (1.49 g) in THF (50 mL) was stirred for 5 hours at 80 C. The precipitate was filtrated through a plug washing with THF to give a crude product that was purified by Biotage eluting with 4/1-hexane/ethyl acetate to give 1.8 g of tert-butyl 4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Chlorophenyl)cyclopropanamine, and friends who are interested can also refer to it.

Reference:
Patent; WANG, TAO; Yin, Zhiwei; Scola, Paul Michael; US2014/135335; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6276-54-6, 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. 6276-54-6 name is 3-Chloropropan-1-amine hydrochloride, 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.

di-tert-butyl dicarbonate(10.89 g, 50mmol)was dissolved in 50 ml THF. The solutionwas cooledto 0 C. 3-Chloropropan-1-amine hydrochloride (6.46 g, 69 mmol) wasdissolved in 20 ml of 1 M NaOH solution and added using a droppingfunnel, and the solution was stirred overnight. 150 ml of ethyl acetatewere added and extraction was performed. The organic phase waswashed three times with water and once with brine, and then driedover magnesium sulfate. The solvent was removed and a viscous oilwas produced, which was dried under vacuum (7.27 g, 68%). 1H NMR(400 MHz, CDCl3) delta (ppm): 4.80 (bs, NH), 3.53 (t, J = 6.4 Hz, 2H),3.22 (q, J = 6.4 Hz, 2H), 1.91 (quin, J = 6.4 Hz, 2H),1.42 (s, 9 H). 13CNMR (100 MHz, CDCl3, delta, ppm): 156, 79, 42, 37, 32, 28.

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

Reference:
Article; Weiss, Ester; Gertopski, Diana; Gupta, Maneesh Kumar; Abu-Reziq, Raed; Reactive and functional polymers; vol. 96; (2015); p. 32 – 38;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

106131-61-7, The chemical industry reduces the impact on the environment during synthesis 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, I believe this compound will play a more active role in future production and life.

General procedure: Dichloro-s-tetrazine (1 mmol) and fluorinated alcohol (1 mmol) were dissolved in anhydrous dichloromethane (10 mL). 2,4,6-collidine (1 mmol) was added dropwise at room temperature in the solution, and the mixture was stirred for 12 h under N2 atmosphere.The solvent was evaporated and the residue was passed through a column of silica (2/8 dichloromethane/petroleum ether v/v) to give compound 2 as a pink solid, with a ?yellow? fluorescence on TLC (using a standard laboratory UV lamp with a broad band centred at 365 nm).

The chemical industry reduces the impact on the environment during synthesis 3,6-Dichloro-1,2,4,5-tetrazine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Ben Chaabane, Radhia; Guermazi, Refka; Clavier, Gilles; Audebert, Pierre; Hedhli, Ahmed; Dyes and Pigments; vol. 108; (2014); p. 64 – 69;,
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. 3972-56-3, name is 1-tert-Butyl-4-chlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., 3972-56-3

General procedure: An oven-dried Schlenk tube was evacuated and backfilled with nitrogen. The Schlenk tube was charged with Pd(bda)2 (11.5 mg,0.02 mmol), L1 (13.7 mg, 0.03 mmol), K3PO4 (424.5 mg, 2 mmol), and toluene (1.0 mL). After stirring for 15 min, the solution of arylhalide (1.0 mmol) and phenol (1.2 mmol) in toluene (1.5 mL) was added. The septum was replaced with an inside reflux condenser, and then the reaction mixture was stirred for 18 h at 110 C. Then,the reaction mixture was cooled to room temperature and quenched with water (5 mL). After separating the organic phase, the aqueous phase was extracted with ethyl acetate (3 mL3), and the combined organic phase was dried over anhydrous Na2SO4. The solvent was concentrated under reduced pressure, and then the crude material was purified by column chromatography on silica gel

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:
Article; Zhang, Yi; Ni, Gang; Li, Chengjun; Xu, Sheng; Zhang, Zhaoguo; Xie, Xiaomin; Tetrahedron; vol. 71; 30; (2015); p. 4927 – 4932;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1435-48-9, A common heterocyclic compound, 1435-48-9, name is 2,4-Dichloro-1-fluorobenzene, molecular formula is C6H3Cl2F, 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.

To a solution of 2,4-Dichloro-1-fluorobenzene (165.0 g, 1.0 mol) in THF (500 mL) n-BuLi (420 mL, 2.5 M, 1.05 mol) was added at -78 C. After stirring at -78 C for 1 h, Oxirane (44.0 g, 1.0 mmol) was added and stirred at -78 C for 2 h. The mixture was quenched with sat. NH4Cl solution, extracted with EtOAc (200 mL * 3). The organic phase was washed with water (100 mL * 2), brine (100 mL * 2), dried over Na2SO4. After filtering, the organic phase was concentrated to give compound 44 as a colorless liquid (156.7 g, 75.0% yield). 1H NMR (400 MHz, CDCl3) delta 7.29-7.25 (m, 1H, Ar-H), 7.02-6.97 (m, 1H, Ar-H), 3.89-3.84 (m, 2H, CH2), 3.29-3.24 (m, 2H, CH2).

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

Reference:
Article; Liu, Na; Wang, Yanfen; Huang, Gongchao; Ji, Conghui; Fan, Wei; Li, Haitao; Cheng, Ying; Tian, Hongqi; Bioorganic Chemistry; vol. 65; (2016); p. 146 – 158;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common compound: 94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 94-97-3

General procedure: To an oven dried Schlenk tube was added 2-halo-substituted ynamide 1 (0.24 mmol), PdCl2(PPh3)2 (5 mol%), benzotriazole 2 (0.29 mmol), KOtBu (0.48mmol) and dry THF (1 mL). The contents were sealed under nitrogen atmosphere and stirred at 70C (oil bath temperature) overnight. After completion of the reaction as monitored by TLC, the crude reaction mixture was passed through a pad of celite and washed with ethyl acetate (20 mL) and concentrated in vacuum. The residue was then purified by using silica gel column chromatography using hexane-ethyl acetate as the eluent to afford benzosultams 3-14

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, 94-97-3, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Siva Reddy, Alla; Leela Siva Kumari; Swamy, K.C. Kumara; Tetrahedron; vol. 73; 19; (2017); p. 2766 – 2773;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 363-51-9, name is 2-Chloro-6-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. 363-51-9.

Example 60A N-(2-chloro-6-fluorophenyl)-4-methyl-2-(methylthio)pyrimidine-5-carboxamide Example 21A (16.5 g, 90 mmol) was dissolved in a mixture of 358 mL of dioxane and thionyl chloride (7.84 ml, 107 mmol). Four drops of N,N-dimethylformamide were added. The reaction mixture was stirred for 30 minutes at ambient temperature then 2-chloro-6-fluoroaniline (17.41 g, 120 mmol) was added and the reaction mixture was stirred at 100 C. overnight. After cooling to room temperature, the reaction mixture was slowly poured into a 1000 mL separatory funnel containing 400 mL of saturated aqueous sodium bicarbonate and the mixture extracted with ethyl acetate (3*200 mL). The combined organic extracts were washed with aqueous sodium bicarbonate (10% wt, 200 mL) and saturated aqueous brine (200 mL), dried over magnesium sulfate, filtered and concentrated. Purification by silica gel flash chromatography (Isco, Redi-Sep column, 2-85% ethyl acetate/hexane, linear gradient) yielded the title compound.

The synthetic route of 2-Chloro-6-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Woods, Keith W.; Mastracchio, Anthony; Lai, Chunqiu; Gandhi, Viraj B.; Penning, Thomas D.; US2013/225589; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common compound: 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 26487-67-2

To a suspension of 60percent sodium hydride (1.6 g) in N,N-dimethylformamide (50 ml) was added 4-bromophenol (3.0 g) under a nitrogen atmosphere, the solution was stirred for 10 minutes at room temperature, then 1-(2-chloroethyl)azepane hydrochloride (4.0 g) and sodium iodide (in catalytic amounts) were sequentially added thereto followed by stirring overnight at 80¡ãC. Water was added thereto followed by stirring, the solution was extracted with ethyl acetate, then sequentially washed with water and brine, and the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (5.0 g).1H-NMR (400MHz, CDCl3); delta (ppm): 1.58-1.67 (m, 8H), 2.73-2.79 (m, 4H), 2.93 (t, 2H), 4.02 (t, 2H), 6.79 (d, 2H), 7.36 (d, 2H).

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, 26487-67-2, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai Co., Ltd.; EP1577288; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics