Month: June 2021

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. 13745-86-3, name is 11-Chlorodibenzo[b,f][1,4]thiazepine, A new synthetic method of this compound is introduced below., Recommanded Product: 13745-86-3

A 1 liter round bottom flask equipped with stirring rod, thermo pocket, water condenser was charged with solution of 11-chlorodibenzo [b,fj[l,4]thiazepine in toluene 350 cc [52 gm (0.22 moles)], and was added 73.0 gm (0.84 moles) of piperazine at 45-50C. The reaction mixture was heated to 70-80C. The reaction mixture was maintained at 70C to 80C for 120-180 min. The reaction mixture was analyzed by HPLC. The reaction mixture was cooled to at 20C to 25C and was added 250 cc DM water and was stirred for 30 min. at 25-30C. The layers were separated and the organic layer washed with 250 cc DM water. The organic layer was forwarded for the next step. Purity of 11- piperazinyldibenzo [b,fj-[l,4] -thiazepine in toluene was more than 97% (area % by HPLC).Example 5. ll-piperazinyldibenzo[b,fl[l,41 thiazepineA 1 liter round bottom flask equipped with stirring rod, thermo pocket, water condenser was charged with solution of l l-chlorodibenzo[b,fj[l,4] thiazepine in toluene [52 gm (0.22 moles)], and was added 73.0 gm (0.84 moles) of piperazine at 45-50C. The reaction mixture was heated to 70-80C. The reaction mixture was maintained at 700C to 80C for 120-180 min. The reaction mixture was analyzed by HPLC (to check for absence of compound of Formula III). The reaction mixture was cooled to at 20C to 25C was added 250 cc DM water and was stirred for 30 min. at 25-30C. The layers were separated and the organic layer washed with 250 cc DM water. To the organic phase was added 250 cc water and was acidified with formic acid to obtain a pH of 2-3. The contents were stirred for 15 min. and the layers were separated. The aqueous layer was washed with 150 cc toluene and the aqueous layer was basified with sodium carbonate to a pH of 8 to 10 and extracted with 3x 250 cc of toluene. Combine the organic layer and washed with DM water 130 cc twice. Purity of 1 l-piperazinyldibenzo[b,f][l,4] thiazepine in toluene was more than 99 % (area % by HPLC). Example 6. 11- piperazinyldibenzo fb,f|-[l.,41 -thiazepineA 1 liter round bottom flask equipped with stirring rod, thermo pocket, water condenser was charged with solution of 11-chlorodibenzo [b,fj[l,4] -thiazepine in toluene [52 gm (0.22 moles)], and the mixture was stirred for 15 min 45-50C.The resulting solution was added piperazine 73.0 gm (0.84 moles) at 45-50C. The reaction mixture was heated to 70-80C. The reaction mixture was maintained at 7O0C to 80C for 120-180 min. The reaction mixture was analyzed by HPLC (to check for absence of compound of Formula III). The reaction mixture was cooled to 20C to 25C, to which, was added 250 cc DM water and was stirred for 30 min. at 25-300C. The layers were separated and the organic layer washed with 250 cc DM water. To the organic phase was added 250 cc water and it was acidified with acetic acid to obtain a pH of 2-3. The contents were stirred for 15 min. and layers were separated. The aqueous layer was washed with 150 cc toluene and the aqueous layer was basified with sodium carbonate to a pH of 8 to 10 and extracted with 3x 250 cc of toluene. Combine the organic layer and washed with DM water 130 cc twice. Purity of 11- piperazinyldibenzo [b,fj-[l,4] -thiazepine in toluene was more than 99 % (area % by HPLC); A 1 liter round bottom flask equipped with stirring rod, thermo pocket, water condenser was charged with solution of l l-chlorodibenzo[b,f][l,4] thiazepine in toluene [52 gm (0.22 moles)], and the mixture was stirred for 15 min 45-50C. To the resulting solution was added piperazine 73.0 (0.84 moles) at 45-50C. The reaction mixture was heated to 70-80C. The reaction mixture was maintained at 70C to 80C for 120-180 min. The reaction mixture was analyzed by HPLC (to check for absence of compound of formula III) and was cooled to 20C to 25C. The reaction mixture was added 250 cc DM water and was stirred for 30 min. at 25-30C. The layers were separated and the organic layer washed with 250 cc DM water. The organic phase was distilled off under vacuum below 70C. Traces of toluene were removed by adding n-butanol. To the resultant oily mass was added 150 cc n-butanol. The mixture was stirred for 24 hrs and chilled to 0-5C. The reaction mass was filtered with the filtrate (mother liquor) containing 11-piperazinyldibenzo [b,fj [l,4]thiazepine. Purity of 11- piperazinyldibenzo[b,fj [1,4] thiazepine in toluene was more than 98.0% (area % by HPLC).Example 9. llpiperazinyldibenzo[b,fl [1,41 thiazepineA 1 liter round bottom flask equipped with stirring rod, thermo pocket, water condenser was charged with solution of 11 -chlorodibenzo [b,f][ 1,4] thiazepine in toluene [52 gm (0.22 moles)], and the mixture was stirred for 15 min 45-50C. To the resulting solution was added piperazine 73.0 gm (0.84 moles) at 45-50C. The reaction mixture was heated to 70-80C. The reaction mixture was maintained at 7O0C to 80C for 120-180 min. The reaction mixture was analyzed by HPLC and was cooled to 20C to 25C. To the reaction mixture was added 250…

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2008/121415; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 108-37-2, name is 1-Bromo-3-chlorobenzene, 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 108-37-2, Application In Synthesis of 1-Bromo-3-chlorobenzene

A mixture of 3-bromo-l-chlorobenzene (191 mg, 1.0 mmol), 2,5- diazabicyclo [2.2.1]heptane-2-carboxylic acid tert-butyl ester (240 mg, 1.2 mmol), sodium tert-butoxide (135 mg, 1.4 mmol), Pd2 (dba)3 mg, 0.03 mmol), and BINAP (56 mg, 0.09 mmol) in toluene (3 mL) was heated to 110 C for 15 h. After cooling to room temperature, the mixture was filtered through celite, and the filter cake was rinsed with ethyl acetate. The solvents were removed in vacuo. Column chromatography on silica (hexanes: ethyl acetate 4: 1) of the residue afforded 5-(3-chlorophenyl)-2,5- diazabicyclo [2.2.1]heptane-2-carboxylic acid tert-butyl ester (240 mg, 78% yield) as a yellow solid. ¹H NMR (400 MHz, CDC13, mixture of rotamers) 8 7.10 (q, 1H), 6.65 (d, 1H), 6.50 (m, 1H), 6.40 (d, 1H), 4.62 (s, 0.5H), 4.48 (s, 0.5H), 3.53 (m, 1H), 3.47-3.67 (m, 2H), 3.20-3.08 (dd, 1H), 1.98-1.91 (m, 2H), 1.45 (s, 4.5H), 1.41 (s,

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

Reference:
Patent; EXELIXIS, INC.; WO2005/117909; (2005); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 93-50-5, name is 4-Chloro-2-methoxyaniline, molecular formula is C7H8ClNO, 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. Computed Properties of C7H8ClNO

1.45g of 4-chloro-2-methoxyaniline was dissolved in a solution of 60 ml of water and 10 ml of concentrated sulfuric acid and cooled to below 5 C in an ice bath. Further, 634 mg of sodium nitrite was dissolved in 1 ml of water and slowly added dropwise to the reaction solution, and the mixture was stirred under ice cooling for 45 minutes, and then 1.98 g of potassium iodide aqueous solution (5 ml) was added dropwise. After stirred at room temperature for 1 hour, the mixture was extracted with EtOAc, washed with a saturated aqueous solution of sodium thiosulfate, dried over anhydrous sodium sulfate and then isolated by column chromatography (PE 100%) to obtain 2.17 g of liquid, yield 88%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 93-50-5, its application will become more common.

Reference:
Patent; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; DUAN, Wenhu; GENG, Meiyu; WANG, Yuming; AI, Jing; FAN, Jun; DAI, Yang; DING, Jian; (133 pag.)EP3486244; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 13526-66-4, The chemical industry reduces the impact on the environment during synthesis 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, I believe this compound will play a more active role in future production and life.

PREPARATION 9; 3-(3-Methoxypyridazin-4-yl)-N-[(1S)-1-phenylethyl]imidazo[1,2-b]pyridazin-6-amine a) 6-Chloro-3-(3-methoxypyridazin-4-yl)imidazo[1,2-b]pyridazine A mixture of 3-bromo-6-chloroimidazo[1,2-b]pyridazine (preparation 1b, 182 mg, 0.78 mmol), 3-methoxy-4-(tributylstannyl)pyridazine (preparation 8b, 313 mg, 0.78 mmol), copper (I) iodide (15 mg, 0.08 mmol) and dry N,N’-dimethylformamide (4 mL) in a Schlenk vial was subjected to three cycles of evacuation backfilling with argon. Tetrakis(triphenylphosphine)palladium (0) (91 mg, 0.08 mmol) was then added and the resulting mixture was subjected to three further cycles of evacuation backfilling with argon before being stirred at 100 ºC for 20 hours. The reaction mixture was cooled down, the solvent was removed under reduced pressure and the residue was purified by flash chromatography (1:1 hexanes/ethyl acetate to 100% ethyl acetate) to give the title compound (131 mg, 64%) as a beige solid. LRMS (m/z): 262 (M+1)+.

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-Bromo-6-chloroimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Almirall, S.A.; EP2463289; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1716-42-3, name is 1-(3-Chloropropoxy)-4-fluorobenzene, 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 1716-42-3, COA of Formula: C9H10ClFO

EXAMPLE 17 4-[Bis(4-fluorophenyl)methyl]-1-[3-(4-fluorophenoxy)propyl]piperidine Following the combined procedures of Examples 14 and 16, 4-[bis(4-fluorophenyl)methyl]piperidine and 4-(3-chloropropoxy)-1-fluorobenzene were reacted and worked up by chromatography in Example 16, to give the free base in 53percent yield as a yellow oil after drying in vacuo at 80° C. overnight. Analysis: Calculated for C27 H28 NOF3: C, 73.78; H, 6.42; N, 3.19. Found: C, 73.64; H, 6.39; N, 3.14.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(3-Chloropropoxy)-4-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; A. H. Robins Company, Incorporated; US4810713; (1989); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 61881-19-4, 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 61881-19-4 as follows.

General procedure: Add sodium acetate, trifluoroethylimidyl chloride (II), hydrazone (III), and 1 mL of organic solvent to the 35 mL Schlenk tube according to the raw material ratio in Table 1.Mix and stir well. After the reaction is completed according to the reaction conditions in Table 2, 2-4 hours,Add elemental iodine, continue the reaction for 1-2 hours, filter, and stir the sample in silica gel.After purification by column chromatography, the corresponding 5-trifluoromethyl-substituted 1,2,4-triazole compound (I) is obtained. The reaction process is shown by the following formula:

According to the analysis of related databases, 61881-19-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang Sci-Tech University; Chen Zhengkai; Hu Sipei; Yang Zuguang; (10 pag.)CN110467579; (2019); A;,
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. 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. Application In Synthesis of 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene

Step 8: (3R, 4R, 5R) -3, 4, 5-tris (benzyloxy) -6- (benzyloxymethyl) -2- (4-chloro-3- (4-ethoxybenzyl) phenyl) tetrahydro-2H-pyran-2-ol (19h) To an ice-cold solution of compound 19g (540 mg, 1.0 mmol) in anhydrous THF (10 mL) was added a solution of (4-chloro-3- (4-ethoxybenzyl) phenyl) magnesium bromide in anhydrous THF (10 mL) , which was prepared freshly from 4-bromo-1-chloro-2- (4-ethoxybenzyl) benzene (486 mg, 1.5 mmol) and magnesium (54 mg, 2.25 mmol) . The reaction mixture was then allowed to stir at room temperature overnight, then quenched with saturated NH4Cl aqueous solution (10 mL) and extracted with ethyl acetate (2×40 mL) . The combined organic phase was washed with H2O (10 mL) , brine (10 mL) , dried (Na2SO4) , and concentrated to produce a residue, which was purified by column chromatography (200300 mesh silica gel, eluted with EtOAc/PE 1:20-1:10) to give compound 19h as a white solid (150 mg, 20) LC-MS (ESI) : 803.36 [M+NH4]+.

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

Reference:
Patent; NATIONAL INSTITUTE OF BIOLOGICAL SCIENCES, BEIJING; ZHANG, Zhiyuan; HUANG, Shaoqiang; ZHANG, Zhaolan; SU, Yaning; REN, Yan; (73 pag.)WO2016/41470; (2016); A1;,
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. 14862-52-3, name is 3,5-Dibromochlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 3,5-Dibromochlorobenzene

Vapor phase chlorination step: A reactor equipped with a lateral reaction tube (diameter of 4 cm, length of 50 cm), a vaporizer and a preheating tube which are capabe of outward temperature control, was used and 1 mol of chlorine gas preheated at 300 C. was fed into the reaction tube and a solution of 1 mol of 1-chloro-3,5-dibromobenzene in 5 mol of carbon tetrachloride was preheated at 300 C. to vaporize it and the vapor was fed into the reaction tube during 50 minutes to react them at 340 C. The residence time of the reaction mixture was about 50 seconds. The discharged gas from the reaction tube was fed into an alkaline aqueous solution of sodium thiosulfate to collect the reaction product. The phase separation was carried out at room temperature and carbon tetrachloride was distilled off to obtain oily product. The oily product was distilled to obtain 165 g. of 1,3,5-trichlorobenzene in yield of 91%.

The synthetic route of 14862-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ishihara Sangyo Kaisha Ltd.; US4368340; (1983); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13334-71-9, name is 4-Chloro-3-methylanisole, molecular formula is C8H9ClO, 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. Formula: C8H9ClO

A solution of 4-chloro-3-methylanisole (3.0 g, 19.2 mmol) (Acros) and potassium permanganate (7.57 g, 47.9 mmol) in water (60 ML) was heated at reflux for 4 h.The precipitate was filtered and the solution was extracted with EtOAc. The aqueous phase was acidified with conc. HCl. The precipitate was collected by filtration, washed with water and dried to give the product. (Yield 0.78 g, 22%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13334-71-9, its application will become more common.

Reference:
Patent; Chen, Jian Jeffrey; Luk, Kin-Chun Thomas; US2004/97493; (2004); 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 2268-05-5 as follows. Formula: C6H3Cl2F

A mixture of 4-chloro-1H-pyrazolo[4,3-c]pyridine (150 mg, 0.990mmol), 1,6-dichloro-2-fluorobenzene (300mg, 1.80mmol) andpotassium carbonate(450 mg, 3.26mmol) in dry DMF(3.0 mL)was heated at 85 C for 20 h.The reaction was quenched with water (30 mL) and extracted withethyl acetate (3 x 20 mL).The combined organic extracts were washed with brine, dried over Na2SO4andconcentrated under reduced pressure.The residue was purified on silica gel(ethylacetate :petroleum ether = 1 : 10)to givethe desired productas a white solid(10 mg, 3.5% yield)anditsregio-isomeras awhitesolid(30 mg, 11% yield).4-Chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine:1H-NMR(CDCl3):delta8.31 (d,J= 0.5 Hz,1H), 8.13 (d,J= 6.0 Hz,1H), 7.64-7.56(m, 3H), 7.49 (m, 1H).LCMS(ESI) m/z: 298.0[M+H+].4-Chloro-1-(2,6-dichlorophenyl)-1H-pyrazolo[4,3-c]pyridine,1H-NMR(CDCl3):delta8.44(d,J= 0.5 Hz,1H), 8.24(d,J= 6.0 Hz,1H), 7.57 -7.47(m, 3H), 7.00(d,J= 6.0 Hz,1H).LCMS(ESI) m/z: 298.0[M+H+].

According to the analysis of related databases, 2268-05-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liang, Jun; Van Abbema, Anne; Balazs, Mercedesz; Barrett, Kathy; Berezhkovsky, Leo; Blair, Wade S.; Chang, Christine; Delarosa, Donnie; DeVoss, Jason; Driscoll, Jim; Eigenbrot, Charles; Goodacre, Simon; Ghilardi, Nico; MacLeod, Calum; Johnson, Adam; Bir Kohli, Pawan; Lai, Yingjie; Lin, Zhonghua; Mantik, Priscilla; Menghrajani, Kapil; Nguyen, Hieu; Peng, Ivan; Sambrone, Amy; Shia, Steven; Smith, Jan; Sohn, Sue; Tsui, Vickie; Ultsch, Mark; Williams, Karen; Wu, Lawren C.; Yang, Wenqian; Zhang, Birong; Magnuson, Steven; Bioorganic and Medicinal Chemistry Letters; vol. 27; 18; (2017); p. 4370 – 4376;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics