Month: July 2021

Related Products of 6775-78-6, These common heterocyclic compound, 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, 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.

Stage 1.2: 3-Bromo-6-chloro-imidazo[1,2-b]pyridazine (II). 6-Chloro-imidazo[1,2-b]pyridazine (I) (example 1; stage 1.1) (4.94 g; 29.3 mMol) is dissolved in DMF (50 mL) and cooled to 0C. At this temperature, N-bromo-succinimide (5.76 g; 30.7 mMol) is added and the brown solution is stirred at OC for 2 h, followed by stirring at RT for 1h. The brown solution is taken up into EtOAc (400 mL) and washed with water (2x 200 mL), followed by back extraction of the aqueous layers with EtOAc (1x 200 mL). The combined organic layers are dried (Na2SO4), and concentrated under reduced pressure to obtain the title compound as yellowish crystals; mp. 132-137C; MS(ESI+):m/z= 233.8 (M+H)+; HPLC: tRet = 4.61 min (System 1). The title compound is used in the next step without further purification. Additional material can be isolated from the mother liquor. The structure is confirmed by x-ray analysis; it contains N-bromo-succinimide.

The synthetic route of 6775-78-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2008/138889; (2008); A2;,
Chloride – Wikipedia,
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Electric Literature of 367-22-6,Some common heterocyclic compound, 367-22-6, name is 4-Chloro-3-fluoroaniline, molecular formula is C6H5ClFN, 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.

[0216] Ethyl 2-(4-chloro-3-fluorophenylamino)-2-oxoacetate (2′). TEA (2.28g, 0.023 mol) was added at once to a solution of 3 g (0.0206 mol) 4-chloro-3-fluoroaniline in 50 ml of DCM and then ethyl 2-chloro-2-oxoacetate (2.81 g, 0.0206 mol) was added dropwise at 0C. Reaction mixture was stirred at 0C for 1 h and then continued at room temperature (RT) for 6 h. The mixture was washed with 25% aqueous solution of K2C03 (2×50 ml) and water (50 ml). The product was dried over Na2S04 and evaporated. The residue was washed with ether and dried on the air to give ethyl 2-(4-chloro-3-fluorophenylamino)-2- oxoacetate (2′) (3.97 g, 78.6%) as a white powder; LC-MS (APCI+) m/z: calcd for C10H9CIFNO3: 245.03; found: 245 (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 4-Chloro-3-fluoroaniline, its application will become more common.

Reference:
Patent; NEW YORK BLOOD CENTER, INC.; THE UNITED STATES OF AMERICA as represented by THE DEPARTMENT OF HEALTH AND HUMAN SERVICES (WASHINGTON, DC); DEBNATH, Asim, Kumar; CURRELI, Francesca; KWONG, Peter, D.; KWONG, Young, Do; WO2013/36676; (2013); A1;,
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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 4152-90-3 as follows. SDS of cas: 4152-90-3

General procedure: The mixture of benzylamine 1a (5.0 mmol), CuI (0.0190 g, 0.1 mmol, 2 mol%), and TEMPO (0.0156 g, 0.1 mmol, 2 mol%) was directly stirred in open air at room temperature (ca. 30 oC) in a reaction tube. After completion of the reaction as monitored by GC-MS and/or TLC, the mixture was then directly purified, without any workup, through a Et3N-washed silica gel column using ethyl acetate and petroleum ether as the eluent, affording N-benzylidenebenzylamine 2a in 85% isolated yield.

According to the analysis of related databases, 4152-90-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Huang, Bo; Tian, Haiwen; Lin, Shoushuai; Xie, Meihua; Yu, Xiaochun; Xu, Qing; Tetrahedron Letters; vol. 54; 22; (2013); p. 2861 – 2864;,
Chloride – Wikipedia,
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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. 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C15H14BrClO

A mixture of 4-bromo-1-chloro-2-(4-ethoxybenzyl)benzene compound of formula-4 (83.33 gms) and toluene (420 ml) was heated to reflux temperature and stirred for 2 hrs under azeotropic conditions. Distilled off the solvent completely under reduced pressure. Cooled the obtained compound to 25-30 C. under nitrogen atmosphere. Tetrahydrofuran (665 ml) followed by the compound obtained in step-(a) were added to the reaction mixture at 25-30 C. under nitrogen atmosphere. Cooled the reaction mixture to -85 to -80 C. and stirred for 20 mins at the same temperature. n-butyl lithium (238.3 ml) was slowly added to the reaction mixture at -85 to -80 C. under nitrogen atmosphere. Raised the temperature of the reaction mixture to -75 to -70 C. and stirred for 2 hrs at the same temperature. A solution of methane sulfonic acid (91.4 ml) in methanol (500 ml) was slowly added to the reaction mixture at -75 to -70 C. The temperature of the reaction mixture was slowly raised to 0-5 C. and then to 10-15 C. The reaction mixture was stirred for 18 hrs at 10-15 C. 10% aqueous sodium bicarbonate solution was added to the reaction mixture at 10-15 C. The temperature of the reaction mixture was raised to 25-30 C. and stirred for 15 mins. Separated the both organic and aqueous layers, the aqueous layer was extracted with ethyl acetate. Both the organic layers were combined, washed with 10% aqueous sodium chloride solution and then distilled off the solvent completely from the organic layer under reduced pressure. Cooled the obtained compound to 40-45 C. and then co-distilled with toluene. Toluene (100 ml) was added to the obtained compound at 25-30 C. and stirred for 20 mins at the same temperature. Diisopropyl ether (500 ml) was added to the reaction mixture at 25-30 C. Cooled the reaction mixture to 15-20 C. and stirred for 2 hrs at the same temperature. Settled the reaction mixture and decanted the upper organic layer. Distilled off the solvent from the bottom to get title compound. Yield: 135 gms; Purity by HPLC: 89.02%.

The synthetic route of 461432-23-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MSN LABORATORIES PRIVATE LIMITED; Thirumalai Rajan, Srinivasan; Eswaraiah, Sajja; (15 pag.)US2017/29398; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 461432-23-5, 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. 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-bromo-1-chloro-2-(4-ethoxybenzyl)benzene (4.9 g, 15 mmol) and 20 mL of tetrahydrofuran were added to a 50 mL three-necked flask, and the mixture was stirred and cooled to -5 to 0 C.Isopropylmagnesium chloride Grignard reagent (8 mL, 2 mol/L) was slowly added dropwise, and the system was stirred at 0 C for 2 h.In another 100mL three-neck bottle, add(2R,3R,4S,5R,6R)-2-bromo-6-(pivaloyloxymethyl)tetrahydro-2H-pyran-3,4,5-tripivalyl ester (IIb, 5.8 g , 10 mmol), tetramethylethylenediamine (5 wt%),Cobalt triacetylacetonate (5 wt%) and 20 mL of tetrahydrofuran were cooled to 0 C.Slowly add the Grignard reagent in the previous 50mL bottle and add it in about 30min.The system was warmed to 25-30 C, stirred under heat for 2 h, and the system was quenched with 1N aqueous hydrochloric acid.The organic phase was extracted with EtOAc, brine and brine.Column chromatography (PE/EA = 6/1) gave the target product (5.4 g, yield 72%).

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-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Fangnan Biological Technology Co., Ltd.; Zhang Nian; (6 pag.)CN104059041; (2018); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 326-64-7, 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. 326-64-7, name is 5-Chloro-2-(trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 5-chloro-2-(trifluoromethoxy)aniline (1.00 g, 4.73 mmol) in acetonitrile (60 mL) and water (6 mL) was added copper(II) bromide (1.48 g, 6.62 mmol). And isopentyl nitrite (0.95 g, 8.13 mmol). The mixture was stirred at 70C for 1 h. It was cooled to rt and quenched with water (200 mL). The mixture was extracted with DCM (60 mL x 2). The combined organic layers were washed with brine (60 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (eluting with petroleum ether) to give the title compound.1H NMR (400 MHz, CDCl3): delta 7.58 (d, J = 2.2 Hz, 1H), 7.29 – 7.22 (m, 1H), 7.19 (s, 1H).

The chemical industry reduces the impact on the environment during synthesis 5-Chloro-2-(trifluoromethoxy)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; XU, Jiayi; ALI, Amjad; ZHOU, Wei; GAO, Ying-Duo; EDMONDSON, Scott, D.; MERTZ, Eric; NEELAMKAVIL, Santhosh, F.; LIU, Weiguo; SUN, Wanying; SHEN, Dong-Ming; HARPER, Bart; ZHU, Cheng; BARA, Thomas; LIM, Yeon-Hee; YANG, Meng; (227 pag.)WO2017/74832; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 13526-66-4, A common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, 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.

Intermediate 2 3-(1-Benzofur-2-yl)-6-chloroimidazo[1,2-b]pyridazine 13.9 g (59.8 mmol) 3-bromo-6-chloro-imidazo[1,2-b]pyridazine were suspended in 508 mL 1,4-dioxane. 10.1 g (62.8 mmol) 2-benzofuranylboronic acid, 2.76 g (2.29 mmol) tetrakis(triphenylphosphino)palladium-(0) and 90 mL (180 mmol) of a 2M aqueous sodium carbonate solution were added. The obtained mixture was heated to 100 C. for 24 h. 400 mL of a saturated aqueous ammonium chloride solution were added. The obtained mixture was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. After evaporation of the solvent, the obtained solid material was digested in 40 mL of a mixture of dichloromethane and methanol (8:2), filtered off and dried in vacuo to yield 5.42 g (44%) of the title compound as solid material. 1H-NMR (300 MHz, DMSO-d6): delta [ppm]=7.23-7.40 (2H), 7.51 (1H), 7.59-7.67 (2H), 7.77 (1H), 8.33-8.40 (2H). LCMS (Method 1): Rt=1.35 min; MS (ESIpos) m/z=270 [M+H]+.

The synthetic route of 13526-66-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Eis, Knut; Puehler, Florian; Zorn, Ludwig; Schulze, Volker; Suelzle, Detlev; Lienau, Philip; Haegebarth, Andrea; Petersen, Kirstin; Boemer, Ulf; US2015/87631; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 622-86-6 as follows. Safety of (2-Chloroethoxy)benzene

a. Diethyl 2,2-di(2-phenoxyethyl)malonate To a stirred solution of sodium (2.3 g) in absolute EtOH (50 ml) was added diethyl malonate (15.2 ml) followed by 2-phenoxyethyl chloride (15. 7 g). The reaction mixture was then refluxed for 12 hr. The EtOH was evaporated under vacuum and the mixture diluted with water (40 ml). The aqueous phase was extracted with Et2 O. The combined Et2 O extracts were washed (brine), dried (MgSO4) filtered and evaporated. Bulb to bulb distillation afforded 12.2 g (27%) of the title diester as a clear liquid, bp 155-175 (106 Pascals, 0.8 Torr); TLC, Rf =0.34, CH2 Cl2.

According to the analysis of related databases, 622-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ICI Americas Inc.; US4910190; (1990); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 50638-46-5,Some common heterocyclic compound, 50638-46-5, name is 4-Bromo-3-chloroanisole, molecular formula is C7H6BrClO, 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.

Step 1: Preparation of 4-hydroxy-1-(2-chloro-4-methoxyphenyl)-2-methylbutan-1-one [0064] To a 1.0 L, 3-neck round bottom flask, equipped with a mechanical stirrer and an internal thermometer, was added a solution of 4-bromo-3-chloroanisole (12.0 g, 54.0 mmol) in 350 mL of THF under nitrogen. The solution was cooled to -85 C. with a MeOH/liquid nitrogen bath. To this solution was added t-BuLi (72.0 mL, 1.6 M in pentane, 122 mmol) slowly followed by the addition of a solution of alpha-methyl-gamma-butyrolactone (9.25 g, 92.0 mmol) in THF (30.0 mL). The internal temperature was controlled <-80 C. After 1 h stirring at <-80 C., the reaction mixture was quenched with saturated NH4Cl solution and warmed to room temperature. Water and EtOAc were added and separated. The aqueous layer was extracted with EtOAc (2×). The combined organic solutions was dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography (E:H, 1:3) to give 10.4 g (79%) of brown oil as the title compound: 1H NMR (400 MHz, CDCl3) delta 7.53 (d, J =8.6 Hz, 1H), 6.97 (d, J =2.4 Hz, 1H), 6.85 (dd, J =8.6, 2.4 Hz, 1H), 3.88 (s, 3H), 3.77-3.69 (m, 2H), 3.64-3.56 (m, 1H), 2.16-2.07 (m, 1H), 1.76-1.67 (m, 1H), 1.23 (d, J=7.0 Hz, 3H); MS (El m/z 241.16 (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 4-Bromo-3-chloroanisole, its application will become more common. Reference:
Patent; Pfizer Inc; US2004/204415; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 6276-54-6, name is 3-Chloropropan-1-amine hydrochloride, molecular formula is C3H9Cl2N, 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. category: chlorides-buliding-blocks

Triethylamine (51.0 g) was added dropwise to a solution of di-tert-butyl dicarbonate (100.0 g) and 3-chloropropylamine hydrochloride (71.5 g) in methanol (400 mL) at 0 C., and the mixture was then stirred at the same temperature for 16 hours. Thereafter, toluene (400 mL) and water (400 mL) were added to the reaction solution for liquid separation, and the organic layer was then washed with water. 400 mL of toluene was added to the organic layer, and the mixed solution was concentrated to 300 mL under reduced pressure. After that, N,N-dimethylacetamide (210 mL) was added, and the mixed solution was concentrated to 300 mL under reduced pressure. Thereafter, to this solution, potassium carbonate (126.66 g), tetrabutylammonium bromide (44.32 g), dimethyl malonate (90.82 g) and N,N-dimethylacetamide (100 mL) were added, and the mixed solution was then stirred at 55 C. for 20 hours. Thereafter, toluene (400 mL) and water (700 mL) were added to the reaction solution for liquid separation. The organic layer was successively washed with water, a 1 M aqueous sodium hydroxide solution and water, and was then concentrated to 150 mL under reduced pressure. To this solution, methanol (1870 mL) and a 1 M aqueous sodium hydroxide solution (430.8 mL) were added, and the mixed solution was then stirred at 0 C. for 27.5 hours. Subsequently, concentrated hydrochloric acid (2.5 mL) was added to the reaction solution, so that the pH of the solution was adjusted to pH 7-9, and the solution was then concentrated to 375 mL under reduced pressure. Ethyl acetate (500 mL) was added to the reaction solution, and concentrated hydrochloric acid (35.1 mL) was then added to the mixed solution, so that the pH of the solution was adjusted to pH 2.2-2.5, followed by liquid separation. The water layer was extracted with ethyl acetate (500 mL), the organic layer was then mixed therewith. The mixed solution was dehydrated and concentrated under reduced pressure to prepare an ethyl acetate (250 mL) solution. To the obtained solution, ethyl acetate (500 mL) and morpholine (37.5 g) were added, and the obtained mixture was stirred overnight. Thereafter, the precipitated crystals were filtrated, were then washed with ethyl acetate, and were then dried under reduced pressure to obtain the title compound (136.1 g, yield: 81.9%). (0118) 1H-NMR (DMSO-d6) delta: 6.79 (1H, t, J=5.5 Hz), 3.61 (4H, t, J=4.9 Hz), 3.58 (3H, s), 3.14 (1H, t, J=7.8 Hz), 2.90-2.80 (6H, m), 1.74-1.59 (2H, m), 1.37 (9H, s), 1.34-1.25 (2H, m) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6276-54-6, its application will become more common.

Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; HAYASHI, Masaki; UKAI, Kazutoshi; (16 pag.)US2018/29993; (2018); A1;,
Chloride – Wikipedia,
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