Tag: M.W=100-200

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. 94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole, A new synthetic method of this compound is introduced below., Safety of 5-Chloro-1H-benzo[d][1,2,3]triazole

General procedure: A typical procedure for the catalytic N-sulfonylation of benzotriazoles using I2 as catalyst includes: in EtOAc-H2O (10:1) mixture solvent (2 mL), benzotriazole 1a (0.3 mmol), sodium benzenesulfinate 2a (0.9 mmol), I2 (0.06 mmol) were added successively. The suspension mixture was vigorously stirred at room temperature for 3 h. Upon completion, the reaction was quenched by addition of sat. aq. Na2S2O3 (2 mL), basified with sat. aq. Na2CO3 (8 mL) and H2O (5 mL). The mixture was extracted with CH2Cl2 (3* 5 mL) and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was then purified by TLC technique (petroleum ether/ethyl acetate = 3:1, v/v) to furnish 1-phenylsulfonylbenzotriazole 3a [28] in 97% yield.

The synthetic route of 94-97-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Si-Xue; Zhang, Yi-Kun; Shi, Hong-Wei; Yan, Jie; Chinese Chemical Letters; vol. 27; 9; (2016); p. 1519 – 1522;,
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Related Products of 112-26-5, 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. 112-26-5, name is 1,2-Bis(2-chloroethoxy)ethane belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2: Preparation of 1N, 1N’-[(3,6-dioxa)-1,8-octyl]-diimidazole 9 Sodiumethoxide and the compound 8 (18.71 g, 0.10 mol) obtained in Step 1 were added to a solution where imidazole (13.62 g, 0.20 mol) is melted in 100 of ethanol. Then, the resultant complex was stirred and heated to reflux till white solids precipitated for six hours. After cooling the complex at room temperature, the solids were filtered and the filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (dichloromethane/methanol=50/50 volume %), thus obtaining a target compound 9 of colorless liquid (22.50 g, 0.089 mmol, 89%). 1H NMR (CDCl3): 3.54-3.56(m, 4H), 3.66(t, 4H, 4.5 Hz), 3.91(t, 4H), 7.98(d, 4H, 1.8 Hz), 9.40(s, 2H, 1.8 Hz)

The synthetic route of 1,2-Bis(2-chloroethoxy)ethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Park, Sang Hyun; Jang, Seung Ho; Gwon, Hui Jeong; Byun, Myung Woo; US2007/173640; (2007); A1;,
Chloride – Wikipedia,
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Electric Literature of 13726-14-2, These common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, 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: Anilines (1 mmol), N,N-dimethylcarbamoyl chloride (2 mmol), DMAP (1 mmol), and pyridine (4mmol) were sequentially added under air to a reaction tube equipped with a stir bar and aseptum. CH2Cl2 (2 mL) was added by syringe and the resulting mixture vigorously stirred for36-48 h at ambient temperature. After this time, the contents of the flask were extracted withEtOAc. The solution obtained was filtered through the plug of silica gel and anhydrous MgSO4,and then concentrated by rotary evaporation. The residue was purified by flash chromatography,eluting with hexane/EtOAc to afford the product.

Statistics shows that 4-Chloro-3-methoxyaniline is playing an increasingly important role. we look forward to future research findings about 13726-14-2.

Reference:
Article; Nishikata, Takashi; Abela, Alexander R.; Huang, Shenlin; Lipshutz, Bruce H.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 1040 – 1064;,
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Electric Literature of 139512-70-2, 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 139512-70-2 as follows.

General procedure: Intermediate compound 5 (0.2 g, 1.24 mmol) and benzil 6d (0.26 g, 1.24 mmol) were weighed and dissolved in 20 mL glacial acetic acid. This mixture was refluxed for 2.5hr. The completion of reaction was monitored by TLC. The reaction mixture was cooled and poured into crushed ice. The precipitated product was filtered off and washed with cold water. The product was then purified by column chromatography using hexane: ethyl acetate as mobile phase. The pure fractions obtained were dried and concentrated to obtain white solids of product 7d. (yield 82%, m.p. 110-112 C).

According to the analysis of related databases, 139512-70-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Patel, Saloni B.; Patel, Bhumika D.; Pannecouque, Christophe; Bhatt, Hardik G.; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 230 – 240;,
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Related Products of 870-24-6, 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. 870-24-6 name is 2-Chloroethanamine 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.

Analog 5, N-(2-Chloroethyl)arachidonylamide. A solution of arachidonic acid (50 mg, 0.165 mmol) and 0.03 mL of anhydrous DMF in 1 mL of dry dichloromethane was cooled in an ice bath under argon and 0.17 mL of a 2 M solution of oxalyl chloride (0.34 mmol) in dichloromethane was added dropwise. Reaction mixture was stirred further at ice bath temperature for 1 hour. A solution of 65 mg (0.50 mmol, 3 equiv) of 2-chloroethylamine hydrochloride in 0.5 mL of dry pyridine was added, the cooling bath was removed, and the solution was stirred at room temperature for 30 min. The mixture was transferred to a separatory funnel, washed with 10% aqueous hydrochloric acid and water, and dried (MgSO4). After rotary evaporation of solvents, the residue was chromatographed on silica gel (60% ethyl ether-petroleum ether) to afford 54 mg (90%) of the pure title compound as an oil: Rf (70% ethyl ether-petroleum ether) 0.35; 1H NMR (270 MHZ, CDCl3) 5.80 (br s, 1H), 5.36 (m, 8H), 3.61 (m, 4H), 2.80 (m, 6H), 2.21 (t, J=7.89 Hz, 2H), 2.10 (m, 4H), 1.72 (m, 2H), 1.29 (m, 6H), 0.88 (t, J=6.79 Hz, 3H). Anal. (C22H36CINO) C, H, N.

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

Reference:
Patent; University of Connecticut; US7161016; (2007); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, 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 2533-69-9, Product Details of 2533-69-9

(a) 2-Trichloromethyl-6-trifluoromethyl-1H-benzoimidazole. To a solution of 4-trifluoromethyl-benzene-1,2-diamine (1.76 g, 10 mmol, Lancaster) in DCM (20 mL) was added methyl 2,2,2-trichloroacetimidate (1.94 g, 11 mmol, Aldrich) and glacial acetic acid (3 mL) with stirring at room temperature. The reaction mixture was stirred at room temperature for 16 h and concentrated in vacuo. The residue was purified by silica gel column chromatography (35% EtOAc/hexane) to give the title compound as a brown solid. MS (ESI, pos. ion) m/z: 303 (M+1).

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

Reference:
Patent; Hulme, Christopher; Ncube, Mghele Vellah; Norman, Mark H.; Ognyanov, Vassil I.; Pettus, Liping H.; Wang, Xianghong; Zhu, Jiawang; US2005/165049; (2005); A1;,
Chloride – Wikipedia,
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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

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

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

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