Month: August 2021

These common heterocyclic compound, 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, 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. Application In Synthesis of 2-(4-Chlorophenoxy)aniline

A solution of 2-(4-chloro-phenoxy)-phenylamine (298 mg, 1.4 mmol), N-(2-acetyl- phenyl)-acetamide, (200 mg, 1.13 mmol) and chlorotriisopropoxytitanium IV (0.53 ml, 2.26 mmol) in toluene (15 ml) was stirred at r.t. for 4 days. NaHCO3 was added and the mixture was extracted repeatedly with EtOAc, dried (MgSO4) and evaporated to dryness. The residue was re-dissolved in THF (20 ml) and cooled to 0 C, to this was added succinic acid (270 mg, 2.26 mmol) and borane (IM in THF, 2.3 ml, 2.26 mmol). The reaction was slowly warmed to r.t. and stirred for 8 h. NaHCO3 was added and the volatile solvents removed in vacuo, the mixture was then extracted with EtOAc and dried (MgSO4). The crude material was purified by flash chromatography (0-100 % DCM in hexane) to yield the product, 79 mg, 19 % yield. LCMS: tr= 1.42 min (95 % MeOH in water), m/z M-H 365.33, HPLC: U= 4.49 min (90 % ACN in water), 97 %,1H NMR (CDCl3, 270 MHz,): delta 1.17 (3H, X, J = 12 Hz, CH3CH2), 1.56 (3H, d, J = 6.7 Hz, CH3CH), 3.10 (2H, q, J= 14.1 Hz, CH2), 4.22 (IH, d, J= 6.0 Hz, NH), 4.53 (IH, q, J = 13.3 Hz, CH), 4.59 (IH, br.s, NH), 6.66-6.93 (7H, m, ArH), 7.01 (IH, td, J= 7.9, 1.5 Hz, ArH), 7.16-7.31 (4H, m, ArH).13C NMR (CDCl3, 68 MHz): 14.9, 19.9 (CH3), 38.1 (CH2), 50.9 (CH), 111.1, 113.6, 117.0, 118.0, 118.6, 119.5, 125.5, 126.5 (ArCH), 128.6, 127.8 (ArC), 128.3, 129.7 (ArCH), 13.7, 143.3, 146.7, 156.4 (ArC).HRMS: Calcd for C22H23ClN2O (M+Na)+ 389.1386, found (M+Na)+ 389.1391.

The synthetic route of 2-(4-Chlorophenoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; STERIX LIMITED; WO2009/66072; (2009); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 106-39-8, 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 106-39-8 as follows.

General procedure: In a thermostatted bath at 25C (or 60C for compounds 18 and 28), a 25 mL Schlenk flask was charged in air with a magnetic stir bar, arylbromide (0.5 mmol), arylboronic acid (0.6 mmol), K2CO3 (0.6 mmol), 1 (26.6 mg, 1mol-%), ethanol (1.5 mL), and water (0.5 mL). The reaction mixture was kept under vigorous stirring until the GC control showed no residual aryl bromide in solution. Water (10 mL) was added to the suspension and the organics were extracted with dichloromethane (3×10 mL). The solution was dried over Na2SO4 and then passed through a column filled with silica gel (diatomaceous earths were used in the case of compound 28). Elimination of the solvent under vacuum gave the desired biaryl as white microcrystalline solid. Purity (96÷99%) was established by GC and 1H NMR. 1H and 13C{1H} NMR data of compounds 8-28. Spin multiplicity is given by s=singlet, br s=broad singlet, q=quartet, st=septet, qq=quartet of quartets, ddd=doublet of doublets of doublets, m=unresolved multiplet. 4-Chloro-4′-methoxy-1,1′-biphenyl (17). Yield 94%. C13H11OCl (218.68): calcd. C 71.40, H 5.07; found C 71.27, H 5.13. 1H NMR (CDCl3): delta = 7.58-7.44 (4H, m), 7.42-7.33 (2H, m), 7.08-6.95 (2H, m), 3.86 (3H, s, OCH3) ppm. 13C NMR (CDCl3): delta = 159.3, 139.2, 132.6, 132.4, 128.8, 128.0, 127.9, 114.3, 55.3 (OCH3) ppm.

According to the analysis of related databases, 106-39-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Del Zotto, Alessandro; Colussi, Sara; Trovarelli, Alessandro; Inorganica Chimica Acta; vol. 470; (2018); p. 275 – 283;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 29671-92-9, 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. 29671-92-9, name is Carbamimidic chloride hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

Step 3; 2-Amino-6- (2-chlorophenoxymethyl)benzonitrile mg; 0.31mmol) and chloroformamidine hydrochloride (53.0 mg, 0.46 mmol) were heated at 140 C in diglyme for 3 hours. The reaction mixture was diluted with water, stirred for 2 hours, filtered, washed with water and dried. Purification by silica gel chromatography (5% methanol in dichloromethane) yielded 50 mg of 5-(2- chlorophenoxymethyl) quinazoline-2,4-diamine.

The chemical industry reduces the impact on the environment during synthesis Carbamimidic chloride hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DECODE CHEMISTRY, INC.; SINGH, Jasbir; GURNEY, Mark E.; WO2005/123724; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, 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 54932-72-8, Recommanded Product: 4-Bromo-1-chloro-2-methylbenzene

Reference Example 5 Preparation of methyl N-(5-bromo-2-chlorobenzyl)carbamate (Compound II-b) A mixture comprising 10.0 g of 5-bromo-2-chlorotoluene, 8.7 g of N-bromosuccinimide, 0.3 g of 2,2′-azobisisobutyronitrile and 60 ml of carbon tetrachloride, was refluxed under heating for 3 hours and, after cooling to room temperature, filtered and concentrated. A mixture comprising the obtained crude product, 5.9 g of potassium cyanate, 10 ml of methanol and 50 ml of N,N-dimethylformamide, was stirred at 100 C. for 2 hours. To this reaction mixture, water was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained crude crystals were washed with isopropanol to obtain 6.8 g of methyl N-(5-bromo-2-chlorobenzyl)carbamate as white crystals.

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; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US6313071; (2001); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 2401-24-3, These common heterocyclic compound, 2401-24-3, name is 2-Chloro-5-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.

6-Chloro-3-methoxyaniline (1.57 g, 10 mmol) was dissolved in ethyl acetate (15 mL)Under ice-cooling,To the above solution was added portionwise1,3-dibromo-5,5-Dimethylhydantoin(3.1 g, ll mmol),After the addition, the reaction solution was allowed to react under ice-cooling for 1 hour,The reaction solution was quenched with saturated potassium carbonate solution,The organic phase was separated,Respectively, with water,Washed with a saturated saline solution,Dried over anhydrous sodium sulfate,Filtered, concentrated under reduced pressure,Bromo-2-chloro-5-methoxyaniline(Brown solid, 1.96 g).

The synthetic route of 2401-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Pharmaceuticals Holding Co., Ltd.; Wan, huixin; Shen, JingKang; Li, ChunLi; Han, yanan; Liu, Haiyan; Zhou, ZhaoLi; Li, Ping; Li, Yufeng; Chen, gang; Xu, Jia; (54 pag.)CN103848785; (2016); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 39885-50-2, name is 2-Chloro-4-(trifluoromethyl)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Chloro-4-(trifluoromethyl)aniline

General procedure: Aniline (140mg, 1.5mmol) and Et3N (202mg, 2mmol) were dissolved in 5mL of dichloromethane and slowly added dropwise to a solution of triphosgene (BTC) (223mg, 0.75mmol) in 10mL of dichloromethane at 0°C. The mixture was then stirred at 0°C for 1h. Then, 5a (300mg, 1mmol) in 1mL of DMF was added at 0°C, and the mixture was then stirred at room temperature for 30min, and the solvent was distilled with a rotary evaporator. The residue was washed with water (10mL×3) and purified via silica gel flash column chromatography to afford 1-(3-((2S,5S)-5-((1H-indol-3-yl)methyl)-3,6-dioxopiperazin-2-yl)propyl)-3-phenylurea (6a) as a pale powder in 74percent yield. Compounds 6b?v, 7a?k and 8a?k were prepared similar to 6a.

The synthetic route of 39885-50-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sun, Haiyang; Li, Hui; Wang, Jiayi; Song, Gonghua; Chinese Chemical Letters; vol. 29; 6; (2018); p. 977 – 980;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 115843-99-7, 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. 115843-99-7 name is 4-Bromo-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.

Anhydrous DMF (60 ml.) is added to a flask charged with bromide 9a (5.00 g, 22.2 mmol), jb/s-(pinacolato)diboron (8.48 g, 33.4 mmol) and potassium acetate (6.35 g, 66.8 mmol) and the resulting suspension is deoxygenated by bubbling a stream of N2 gas through the mixture for about 45 min. 1 , 1 ‘-bis(diphenylphosphino)ferrocene (2.73 g, 3.34 mmol) is then added and the mixture is deoxygenated for approximately a further 5 min and is then heated to 950C. After about 16 h, the dark reaction mixture is cooled, extracted with EtOAc (500 mL and 300 mL) and washed with 1 :1 water/brine (600 ml.) and brine (600 mL). The combined extracts are dried over anhydrous MgSO4, filtered and evaporated to a black syrup which is purified by flash column chromatography (EtOAc / hexanes) to afford the boronate 9b as white solid contaminated with <25 % of the diboron reagent (4.24 g, 62% yield). At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-3-chloro-2-fluoroaniline, and friends who are interested can also refer to it. Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; WO2009/62308; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 39885-50-2,Some common heterocyclic compound, 39885-50-2, name is 2-Chloro-4-(trifluoromethyl)aniline, molecular formula is C7H5ClF3N, 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 6 A mixture (301 g) of 2-chloro-4-trifluoromethylaniline, 2-chloro-5-trifluoromethylaniline and N-methylpyrrolidone (NMP) (1.06 m/m) was mixed with 500 ml chlorobenzene. Sulfuryl chloride (148.4 g) was added to the mixture at 55-60° C. over a period of 4 hours and the reaction mixture was maintained at 55-60° C. for 4 hours. Reaction medium on treatment and fractionation gave 0.84 m of 2,6-dichloro-4-trifluoromethylaniline, 95percent yield on 2-chloro-4-trifluoromethyl aniline.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-4-(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; Gharda, Keki Hormusji; US2013/30190; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1996-30-1, These common heterocyclic compound, 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, 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: E0 (1.00 equivalent), bromo-chloro-fluorobenzene (1.00 equivalent) tris(dibenzylideneacetone)dipalladium(0) Pd2(dba)3 (0.04 equivalents, CAS: 51364-51-3), XPhos (0.08 equivalents, CAS 564483-18-7) and potassium phosphate (K3PO4, 3.0 equivalents) are stirred under nitrogen atmosphere in toluene/H2O (10:1) at 100 C for 16 h. After cooling down to room temperature (RT) and the reaction mixture is extracted with ethyl acetate/brine. Organic phase is collected, washed with brine and dried over MgSO4. The organic solvent is removed, the crude is recrystallized from toluene.

The synthetic route of 1996-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CYNORA GMBH; SZAFRANOWSKA, Barbara; ZINK, Daniel; (205 pag.)WO2019/101746; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, 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: 1127-85-1

9a) 2-(4-(2-Chloro-5,6,7,8-tetrahydrocuinazolin-4-yloxy)phenyl)acetic acid methyl ester 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline (300 mg, 1.477 mmol), 2-(4-hydroxyphenyl)acetic acid methyl ester (245 mg, 1.477 mmol) and potassium carbonate (408 mg, 2.95 mmol) in DMF (4 ml) were stirred for I h at 80C. After adding water the precipitated solid was filtered off, washed with water and dried under vacuum. White solid. Yield: 441 mg (90% of theory)LC-MS (method 1): R 2.43 mm, m/z [M+H] 333 (ES)

The synthetic route of 1127-85-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; KONETZKI, Ingo; JAKOB, Florian; CRAAN, Tobias; HESSLINGER, Christian; RATCLIFFE, Paul; SHIERS, Jason J.; WO2014/117948; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics