Author: Jessica.F

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. 108-70-3, name is 1,3,5-Trichlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,3,5-Trichlorobenzene

In a nitrogen-filled glove box, a 50 mL pressure flask wascharged with 1,3,5-trichlorobenzene (13.68 g, 75.40 mmol),0.67 mL of chloroform (1.00 g, 8.37 mmol), aluminum trichloride(1.22 g, 9.14 mmol), and a magnetic stir bar. This mixture washeated to 90 C for 2 h under an atmosphere of nitrogen. After thistime the mixture was allowed to cool to room temperature and 20 ml of HCl (0.1N) was added drop-wise over this mixture whichwas cooled in an ice bath. The purple suspension immediatelyturned into a yellow solution that was then extracted from theaqueous byproducts using 50 mL of chloroform in a separatoryfunnel. The organic layer was dried over magnesium sulfate for 1 hand filtered over a scintillated glass frit. The yellow solution wasimmediately concentrated under vacuum and the obtained oilymaterial was added to 40 mL of hexanes which resulted in theimmediate precipitation of a white solid. The solid was collected ona frit, and washed with hexanes until the washings were colorless.The white solid was dried under vacuum to get an 80% yield whichwas used in the next step without further purification. m.p. 246-248C. 1H NMR (400 MHz) (CDCl3): d 6.68 (s, 1H, CHPh), 7.23e7.24(d, 3H, J 2.3 Hz), 7.35e7.36 (d, 3H, J 2.3 Hz). 13C NMR(100.61 MHz): delta 49.80(CH), 128.43, 130.00, 133.78,133.82, 137.07,137.90. The synthesis has been modified slightly and the purificationprocess as well. Characterization data of this compound is inagreement with those reported in the literature [16].

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 108-70-3.

Reference:
Article; Neier, Eric; Arias Ugarte, Renzo; Rady, Nader; Venkatesan, Swaminathan; Hudnall, Todd W.; Zakhidov, Alexander; Organic electronics; vol. 44; (2017); p. 126 – 131;,
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Some common heterocyclic compound, 2267-25-6, name is 2-Chloro-4-fluoroanisole, molecular formula is C7H6ClFO, 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. Application In Synthesis of 2-Chloro-4-fluoroanisole

Sodium hydride (60% dispersion in mineral oil, 31 mg, 0.776mmol) was added to an ice- cooled solution of the product of preparation 20 (135mg, 0.388mmol) in N1N- dimethylformamide (4mL) and the mixture was stirred at O0C for 15 minutes. 2-chloro-4-fluoro- anisole (93mg, 0.582mmol) in N,N-dimethylformamide (1mL) was added and the mixture was stirred for 16 hours, at 5O0C. The solution was cooled to 250C and sodium hydride (60% dispersion in mineral oil, 62mg, 1.55mmol) was added and the solution was stirred for 16 hours at 80C. The reaction mixture was then cooled to 25C and quenched with water (3mL), concentrated in vacuo and the aqueous residue was partitioned between ethyl acetate (2OmL) and water (5mL). The aqueous layer was separated and extracted with ethyl acetate (2x20mL). The combined organic solution was washed with brine (1OmL), concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with pentane: (ethyl acetate:methanol;0.88ammonia, 90:10:1), 3:1 to 1:1. The product containing fractions were evaporated under reduced pressure and the residue was further purified using an Isolute SCX-2 cartridge, eluting with methanol followed by 1M ammonia in methanol. The basic fractions were evaporated to afford the title compound as a yellow gum in 32% yield, 61mg.1HNMR(400MHz, CD3OD) delta: 1.03(s, 3H), 1.08(s, 3H), 1.28-1.31(m, 2H), 1.76-1.80(m, 1H), 1.86-1.93(m, 1H), 2.09-2.18(m, 1H), 2.49-2.63(m, 2H), 2.67-2.70(m, 1 H), 2.76-2.87(m, 2H), 3.80(s, 3H), 4.71-4.75(m, 1H), 6.74-6.77(dd, 1H), 6.89-6.95(dd, 1H), 7.24-7.46(m, 10H), 8.45- 8.59(m, 1 H); LRMS APCI m/z 489 [M+H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2267-25-6, its application will become more common.

Reference:
Patent; PFIZER LIMITED; WO2007/34325; (2007); A1;,
Chloride – Wikipedia,
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Electric Literature of 2533-69-9, 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. 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 2,2,2-trichloroacetimidate (1.53 g) in acetic acid (10 ml) was added a solution of 4-fluorobenzene-1,2-diamine in acetic acid (10 ml) under ice-cooling, followed by stirring at room temperature for 3 hours. The reaction liquid was concentrated under reduced pressure and to the obtained residue was added water, followed by neutralization with a saturated aqueous sodium hydrogen carbonate solution and extraction with EtOAc. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from iPr2O/EtOAc/MeOH to obtain 5-fluoro-2-(trichloromethyl)-benzimidazole (1.5 g) as a beige powder.

The chemical industry reduces the impact on the environment during synthesis Methyl 2,2,2-trichloroacetimidate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Astellas Pharma Inc.; EP2351749; (2011); A1;,
Chloride – Wikipedia,
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Reference of 33786-89-9,Some common heterocyclic compound, 33786-89-9, name is 5-Chloro-m-phenylenediamine, molecular formula is C6H7ClN2, 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.

STR4 Using the above description one ordinarily skilled in the art can make and use the compounds of this invention. Specific embodiments of the invention are provided below. Structures and names of the embodied compounds are found summarized in CHART C. The examples below serve to illustrate the invention and are not intended to limit the invention in any manner. Example 1. Synthesis of N-(3-azido-5-ehlorophenyl)-N’-cyano-N”-(1,1dimethylpropyl)guanidine. Chart A. Step A-2. A stirred solution of 5-chloro-1,3-phenylenediamine (A-1, X is Cl, 1.93 g, 13.5 mmol) in 55 mL of dichloromethane is cooled to 0 C. and di-tert-butyl dicarbonate (2.96 g, 13.5 mmol) is added. The reaction mixture is stirred at 20-25 C. for 5 days and then concentrated. The residue is purified by medium pressure liquid chromatography using 25% ethyl acetate in hexane to afford 2.20 g of 3-amino-5-chlorophenylcarbamic acid, 1,1-dimethylethyl ester. (A-2) mp 85-87 C.; IR (mull) 3439, 3357, 3328, 2926, 1691, 1613, 1589, 1524, 1475, 1438, 1391, 1366, 1311, 1274, 1240, 1159, 851 cm-1; 1 H NMR (CDCl3) delta6.77 (bs, 1 H), 6.64 (m, 1 H), 6.39 (bs, 1 H), 6.34 (m, 1 H), 3.73 (bs, 2 H), 1.50 (s, 9 H); 13 C NMR (CDCl3) delta152.1, 147.8, 139.9, 134.8, 109.4, 108.2, 102.6, 80.5, 28.2; Analysis calculated for C11 H15 CIN2 O2: C, 54.44; H, 6.23; N, 11.54; Cl, 14.61. Found: C, 54.27; H, 6.50; N, 10.96; Cl, 13.99.

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

Reference:
Patent; The Upjohn Company; US5525742; (1996); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 2687-12-9, name is Cinnamyl 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. Quality Control of Cinnamyl chloride

General procedure: Aryl, benzyl or allyl halides (1.0mmol), arylboronic acid (1.2mmol), K2CO3 (1.5mmol), C1 (5×10-6 mol%) and H2O (2.0mL) were added into a sealed tube and the mixture was stirred at 60C for a few hours. After the reaction, the aqueous phase was extracted with ethyl acetate for 3 times (3×7mL). Then the combined organic layers were dried over anhydrous Na2SO4, concentrated under vacuum and purified by column chromatography.

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

Reference:
Article; Luo, Kaixiu; Zhang, Lu; Yang, Rui; Jin, Yi; Lin, Jun; Carbohydrate Polymers; vol. 200; (2018); p. 200 – 210;,
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Synthetic Route of 13726-14-2, The chemical industry reduces the impact on the environment during synthesis 13726-14-2, name is 4-Chloro-3-methoxyaniline, I believe this compound will play a more active role in future production and life.

General procedure: Procedure B: A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.), and substituted aniline (1.0-1.05 equiv.), and DIPEA (1.2 equiv.) in isopropanol (0.1 M) was stirred and heated at reflux. The reaction time, work-up, and product isolation procedure are described below.

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

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); A1;,
Chloride – Wikipedia,
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Related Products of 29671-92-9,Some common heterocyclic compound, 29671-92-9, name is Carbamimidic chloride hydrochloride, molecular formula is CH4Cl2N2, 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 7 Synthesis of 2-amino-8-chloro-3H-benzo[4,5]furo[3,2-d]pyrimidin-4-one; To a solution of S-amino-S-chlorobenzofuran-l-carboxylic acid methyl ester (5.0 g, 22.16 mmol, 1 eq) in sulfolane (25 ml) is added chloroformamidine hydrochloride (3.82 g, 33.24 mmol, 4.5 eq) at 100 0C and the reaction mixture is stirred further at 160 0C for an hour, it is cooled down to 50 0C and diluted with methanol (75 ml), the precipitated product is filtered off, dried in vacuo at 80 0C. A yellowish solid (3.85 g, 16.34 mmol, 73.73%) is obtained.1H NMR (DMSO-de): 7.67 (dd, IH), 7.82 (d, IH), 8.06 (d, IH)

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

Reference:
Patent; CELLZOME (UK) LTD.; WO2008/62013; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 64628-73-5, 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. 64628-73-5, name is 3-Chloro-4-(trifluoromethoxy)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-Bromo-7-fluoro-1H-indole-2-carboxylic acid ethyl ester (200 mg, 0.7 mmol) was dissolved in toluene (16 mL), and Pd2 (dba) 3 (64 mg, 0.07 mmol) and Davephos (55 mg) were sequentially added. , 0.14mmol) and K3PO4 (401mg, 2.1mmol, 2.1mLH2O), after stirring well, 3-methoxy-5-trifluoromethylaniline (444mg, 2.10mmol) in toluene (4mL) was added, argon Under protection, the reaction was refluxed overnight with a small amount of starting material remaining. Cool to room temperature, concentrate, add EA (30mL) to dissolve the residue, 6N hydrochloric acid (10mL × 2), wash with saturated brine (20mL × 3), wash with water (20mL × 2), column chromatography (P / E = 20: 1 10: 1) to obtain 225 mg of off-white solid, yield 81.2%, melting point: 143-145 C.

The synthetic route of 3-Chloro-4-(trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xu Boling; Chen Xiaoguang; Cui Guonan; Lai Fangfang; Zhou Jie; Ji Ming; Wang Xiaoyu; Du Tingting; Li Ling; Jin Jing; (144 pag.)CN110483366; (2019); A;,
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2268-05-5, name is 2,6-Dichlorofluorobenzene, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 2268-05-5

tert-Butyl 4-(3-oxo-2,3-dihydro-1H-indazol-1-yl)benzoate (300 mg; 0.97 mmol; 1.00 eq.), 1,3-dichloro-2-fluoro-benzene (1.59 g; 9.67 mmol; 10.0 eq.), potassium carbonate -325Mesh (267 mg; 1.93 mmol; 2.00 eq.) and 1-methyl-2-pyrrolidinone (5.00 mL) were stirred at 200 C for 4 hours in a sealed tube. The reaction mixture was cooled, diluted in ethyl acetate (50 mL) and water (50 mL). The pH of the aqueous layer was adjusted to 1 using a 3 M solution of hydrochloric acid. The aqueous layer was extracted with ethyl acetate (50 mL). The combined organic layers were dried over MgSO4,concentrated and purified by preparative HPLC.4-(3-(2,6-dichlorophenoxy)-1H-indazol-1-yl)benzoic acid was isolated as a beige solid (120 mg; 29.0 %).1H NMR (DMSO-d6) delta: 7.47 – 7.35 (m, 2H), 7.75 – 7.61 (m, 5H), 7.92 – 7.86 (m, 1H), 8.00 (d,J =8.7 Hz, 1H), 8.10 – 8.04 (m, 2H), 13.02 (s, 1H).MS-ESIm/z399 [MH+].

The synthetic route of 2268-05-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ouvry, Gilles; Bouix-Peter, Claire; Ciesielski, Fabrice; Chantalat, Laurent; Christin, Olivier; Comino, Catherine; Duvert, Denis; Feret, Christophe; Harris, Craig S.; Lamy, Laurent; Luzy, Anne-Pascale; Musicki, Branislav; Orfila, Danielle; Pascau, Jonathan; Parnet, Veronique; Perrin, Agnes; Pierre, Romain; Polge, Gaelle; Raffin, Catherine; Rival, Yves; Taquet, Nathalie; Thoreau, Etienne; Hennequin, Laurent F.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 23; (2016); p. 5802 – 5808;,
Chloride – Wikipedia,
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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 2106-04-9 as follows. Formula: C6H5ClFN

Preparation of compound 18[00187] A solution of compound 17 (5g, 0.034mol) in DMF (50mL) was added a DMF solution (50mL) of NBS (6.05 g, 0.034 mol) drop-wise at room temperature. After 16h, the reaction mixture was diluted with ethyl acetate (lOOmL) and washed with brine (2xl00mL). The separated organic phase was dried over Na2S04 and concentrated to give the title compound 18 as an oil (5.0g, 65% yield). ESI-MS (M+H)+: 223.92.

According to the analysis of related databases, 2106-04-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TONG, Youzhi; WO2011/29392; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics