Category: chlorides-buliding-blocks

Application of 6276-54-6, 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 6276-54-6 as follows.

To a solution of phenol A4 (80 mg, 0.22 mmol, 1.0 equiv) indry CH3CN (4 mL) was added tetrabutylammonium hydrogen sulfate (16.0 mg, 0.05 mmol, 0.21 equiv) and powdered NaOH (32 mg, 0.80 mmol, 3.6 equiv). This mixture was then allowed to stir at room temperature for 30 minutes, at which point 1-Amino-3-chloropropane hydrochloride (58 mg, 0.45 mmol, 2.0 equiv) was added to the solution. The mixture was then placed in an oil bath that had been preheated to 55 C, and was allowed to stir at this temperature for 14 hours.Following determination of reaction completion by TLC and LCMS analysis, the solution was then removed from the oil bath and allowed to cool to room temperature. Upon cooling, the mixture was diluted with EtOAc (20 mL) prior to the addition of H20 (10 mL), which served to dissolve all of the inorganic solids present. Following separation of the layers, the aqueous layer was extracted with EtOAc (20 mL). The organic layer was then washed with brine (10 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was then purified through flash column chromatography (12 g silica gel cartridge, 0-100% EtOAc/Hexanes, followed by 0-20% MeOHICH2C12, and desired product eluted during 20%MeOH, to yield the desired product (65.0 mg, 70%) as a yellow solid. ?H NIVIR (400 MHz,CHLOROFORM-d) 7.13 (d, J= 8.52 Hz, 2H), 6.85 (d, J = 8.52 Hz, 2H), 3.96-4.13 (m, 2H),2.94 (t, J = 6.70 Hz, 2H), 2.67-2.89 (m, 1H), 2.20 -2.28 (m, 2H), 2.09 -2.15 (m, 1H), 1.91 -2.04 (m, 8H), 1.66 – 1.86 (m, 12H), 1.50 – 1.66 (m, 1H), 1.22 – 1.49 (m, 2H); 13C NMR (100IVIHz, CHLOROFORIVI-d) 157.4, 138.1, 127.8, 114.5, 111.5, 109.3, 76.8, 66.0, 42.5, 41.2,39.3, 36.9, 36.6, 36.5, 35.0, 35.0, 34.9, 34.9, 34.3, 33.2, 32.7, 27.0, 26.6, 23.7; MS (ESI)calculated for C25H36N04 [M + H] m/z 414.26, found 414.17

According to the analysis of related databases, 6276-54-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; TALUKDER, Poulami; RENSLO, Adam, Robert; BLANK, Brian, Richard; MUIR, Ryan, Keith; EVANS, Michael, John; (270 pag.)WO2019/5977; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 1435-44-5, 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. 1435-44-5 name is 1-Chloro-2,4-difluorobenzene, 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.

1-Chloro-2,4-difluoro-5-nitrobenzene: To a stirred solution of 1-chloro-2,4-difluorobenzene (0.829 g, 5.58 mmol, Aldrich, used as received) in conc. H2 SO4 (8.0 mL) at 0 C., KNO3 (0.565 g, 5.59 mmol) was added in one lot. The resulting solution was allowed to warm to 28 C. and stirred overnight at 28 C. It was then poured into ice (80 g) and extracted with ethyl acetate (75 mL). The ethyl acetate was dried over anhydrous Na2 SO4, removed under vacuum, and the resulting oil was dried further under vacuum to afford 1.007 g (93%) of the pure (1 H NMR) title compound as a light red oil; 1 H NMR (CDCl3): delta7.168 (dd, 1H, J1 =9.9 Hz, J2 =8.4 Hz), 8.238 (t, 1H, J=7.5 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Chloro-2,4-difluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; State of Oregon, acting by and through the Oregon State Board of Higher Education, acting for and on behalf of the Oregon Health Sciences University and the University of Oregon, Eugene Oregon; Acea Pharmaceuticals, Inc.; The Regents of the University of California; US5631373; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 112581-77-8, 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. 112581-77-8, name is 2,6-Dichloroimidazo[1,2-b]pyridazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Zinc chloride (2.04 g, 15.0 mmol) was dried at 180C for 2 hours under vacuum and then cooled to room temperature, and anhydrous tetrahydrofuran (20.0 mL) was added thereto. n-Butyl lithium (1.6 M, 9.0 mL, 14.4 mmol) was added dropwise thereto over about 30 minutes under ice-cooling and stirred for 30 minutes under ice-cooling, to prepare a solution of n-butylzinc chloride in tetrahydrofuran. Separately, a suspension of 2,6-dichloroimidazo[1,2-b]pyridazine (1.88 g, 10.0 mmol) and [1,3-bis(diphenylphosphino)propane]nickel (II) dichloride (0.16 g, 0.30 mmol) in anhydrous tetrahydrofuran (20.0 mL) was prepared under a nitrogen atmosphere, and the previously prepared solution of n-butylzinc chloride in tetrahydrofuran while being maintained at 3 to 6C was added dropwise thereto over 30 minutes. The mixture was stirred for 15 minutes under ice-cooling and for 3 hours at room temperature, then poured into a saturated saline solution and adjusted to pH 2 with dilute hydrochloric acid. The reaction solution was extracted twice with ethyl acetate, and the extracts were combined, dehydrated over anhydrous magnesium sulfate and concentrated under reduced pressure. The residues were purified by silica gel column chromatography (ethyl acetate : hexane = 1 : 4), to give the title compound as pale yellow crystals. The yield was 2.03 g (96.8%). mp 61.0-63.0C1H NMR (CDCl3, delta): 0.96(3H, t, J=7.3 Hz), 1.41(2H, tq, J=7.5, 7.3 Hz),1.73(2H, tt, J=7.8, 7.5 Hz), 2.81(2H, t, J=7.8 Hz), 6.96(1H, d, J=9.4 Hz), 7.74(1H, d, J=9.4 Hz), 7.79(1H, s). IR(Nujol, cm-1): 3115, 3061, 1545, 1466, 1378, 1326, 1276, 817.

The synthetic route of 2,6-Dichloroimidazo[1,2-b]pyridazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Takeda Agro Company, Limited; EP1466527; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 328-84-7, 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. 328-84-7, name is 3,4-Dichlorobenzotrifluoride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 1 Synthesis of 2,3-dichloro-6-trifluoromethylbenzaldehyde STR10 54 g (0.25 mol) of 3,4-dichlorobenzotrifluoride was dissolved in 500 ml of anhydrous THF, and cooled down to -70 C. with dry ice/acetone. To the solution, 190 ml (0.3 mol) of hexane solution of n-butyl lithium was added dropwise over 45 minutes, while keeping the temperature at -70 C. The reaction solution was matured for an hour at -70 C., then 30 g (0.5 mol) of methyl formate was dropped into the solution over 30 minutes, while keeping the temperature at -70 C. After the reaction solution was matured for an hour at -70 C., the temperature of the solution was elevated to room temperature. The reaction solution was poured into ice water and extracted with ether. The organic layer obtained was washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled out under reduced pressure. The resulting residue was distilled to give 47.3 g of oily product. Yield 77% (purity 95%), 84~94 C./3mmHg.

The synthetic route of 3,4-Dichlorobenzotrifluoride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Soda Co., Ltd.; US5977414; (1999); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 303-49-1, name is 3-(3-Chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-(3-Chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine

Clomipramine 2 (0.503 g; 1.43 mmol; 1 equiv) was mixed with Cs2CO3 (1.13 g; 3.57 mmol; 2.5 equiv) and XPhos precatalyst PdG1 (0.0313 g; 0.0428 mmol; 3 mol %) in a glove box. To this anhydrous acetonitrile (4 mL) was added, and the reaction mixture was left with stirring, in the glove box for 25 min before THP protected propargyl alcohol (0.501 g; 3.57 mol; 2.5 equiv) was added. The reaction vessel was sealed, removed from the glove box, and then heated to 80 C for 20 h. After 20 h the reaction mixture was cooled to rt and quenched with saturated NaHCO3 (aq). The mixture was extracted with AcOEt, and the combined organic phases were dried over MgSO4, filtered and evaporated. The product was purified by column chromatography (first CH2Cl2/CH3OH 50:1 then CH2Cl2/CH3OH 20:1). Upon repeated column chromatography, the product was isolated as brown oil in 63% yield (0.375 g; 0.895 mmol). Rf (CH2Cl2/CH3OH 20:1) 0.45. 1H NMR (400 MHz, CDCl3) deltaH 7.16-7.02 (m, 4H), 6.99 (s, 2H), 6.94 (dt, 1H, J = 7.3, 1.1 Hz), 4.88 (t, 1H, J = 3.4 Hz) 4.46 (q, 2H, J = 15.7 Hz), 3.93-3.81 (m, 1H), 3.77 (t, 2H, J = 6.6 Hz), 3.61-3.50 (m, 1H), 3.12 (s, 4H), 2.60 (t, 2H, J = 5.6 Hz), 2.35 (s, 6H), 1.96-1.48 (m, 8H). 13C NMR (100 MHz, CDCl3) deltaC 147.9, 134.9, 134.4, 130.3, 129.7, 126.7, 125.9, 123.3, 123.2, 120.7, 120.4, 96.9, 86.0, 84.4, 62.1, 57.3, 54.9, 48.5, 44.9, 32.6, 31.8, 30.4, 25.5, 19.2 ppm. HRMS (ES+): Calcd for C27H34N2O2H: 419.2699; found 419.2699.

According to the analysis of related databases, 303-49-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Brink¡ã, Anne; Larsen, Maja T.; Kolds¡ã, Heidi; Besenbacher, Louise; Kolind, Anders; Schi¡ãtt, Birgit; Sinning, Steffen; Jensen, Henrik H.; Bioorganic and Medicinal Chemistry; vol. 24; 12; (2016); p. 2725 – 2738;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 13078-79-0, 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 13078-79-0 as follows.

Example S15; Preparation of (4-tert-butyl-benzyl)-[2-(3-chloro-phenyl)-ethyl]-amine; 0.38 ml of 4-tert-butylbenzaldehyde (2.25 mmol) and 0.215 ml 2-(3-chloro-phenyl)-ethylamine (1.5 mmol) were dissolved in 4.5 ml methanol at rt, and after stirring for 30 min at rt, were refluxed for 2.5 h. After cooling down to rt, 85 mg (2.25 mmol) sodium borohydride were added and after stirring for 5 min at rt, the reaction mixture was then refluxed for 4 h. After cooling down to rt, the reaction mixture was treated with 4 drops 1 N HCl and concentrated in vacuo. The residue was diluted with water/EtOAc. After separation of the organic phase, the aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried with magnesium sulfate, filtered off and concentrated in vacuo. The residue was purified by column chromatography (40 g silica gel; EtOAc/heptane 1:2) to give 465 mg light yellow oil (100%). MS (ISP) 302.3 (M+H)+.

According to the analysis of related databases, 13078-79-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Conte-Mayweg, Aurelia; Kuehne, Holger; Luebbers, Thomas; Maugeais, Cyrille; Mueller, Werner; Pflieger, Philippe; US2006/30613; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 210532-25-5, 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. 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3,5-difluorobenzenesulfonyl chloride (25 g, 0.117 mol) in THF (150 mL) was added 35% aq. NH4OH (120 mL) over 1 h in an ice-bath. After the reaction was complete, it was evaporated in vacuo. To a solution of this residue in water (150 mL) was added 2N HC1 (1 mL). After stirring 1 h, the reaction mixture was filtered and dried under high vacuum to give 3,5-difluorobenzenesulfonamide as a light brown solid (19.9 g, 88%). 1H NMR (400MHz, CDC13) delta 7.49-7.44 (m, 2H), 7.04-6.99 (m, 2H).

The chemical industry reduces the impact on the environment during synthesis 3,5-Difluorobenzene-1-sulfonyl chloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; EXELIXIS, INC.; BOLLU, Venkataiah; BOREN, Brant, Clayton; DALGARD, Jackline; FLATT, Brenton, T.; HAQ, Nadia; HUDSON, Sarah; MOHAN, Raju; MORRISSEY, Michael; PRATT, Benjamin; WO2011/71565; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, A new synthetic method of this compound is introduced below., Quality Control of 4-Bromo-2-chloro-1-fluorobenzene

Example 112 Production of (4aS, 8aR)- 1 -(3 -chloro-4-fluoropheny l)-3 , 3 -dimethy ldecahydroquinoxaline hydrochloride bsolute configuration A toluene (10 ml) suspension of (4aR,8aS)-2,2-dimethyldecahydroquinoxaline (168 mg, 0.998 mmol), 4-bromo-2-chloro-l-fluorobenzene (251 mg, 1.20 mmol), Pd(OAc)2 (11.2 mg, 0.0500 mmol), t-Bu3P.HBF4 (14.5 mg, 0.0500 mmol), and NaOt-Bu (135 mg, 1.40 mmol) was stirred for 5 hours under reflux in a nitrogen atmosphere. The reaction solution was cooled to room temperature. Then, water (0.5 mL) and AcOEt (10 mL) were added thereto, and the mixture was stirred. MgS04 was further added thereto, and the mixture was stirred. Then, insoluble matter was filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by basic silica gel column chromatography (Hex- AcOEt). The obtained oil was dissolved in 1 N HCl-EtOH (3 mL), and ethanol was distilled off under reduced pressure. The deposited crystal was recrystallized from ethanol/acetone to obtain (4aS,8aR)-l- (3-chloro-4-fluorophenyl)-3,3-dimethyldecahydroquinoxaline hydrochloride (153 mg, yield: 46%) in a white powder form. 1H-NMR ( DMSO-de ) 6ppm : 1.15-1.45 ( 6H, m ), 1.51 ( 3H, s ), 1.6-1.9 ( 4H, m ), 1.9-2.05 ( 1H, m ), 2.94 ( 1H, d, J = 13.5Hz ), 3.3-3.45 ( lH, m ), 3.65-3.8 ( 1H, m ), 3.95-4.1 ( 1H, m ), 6.85-7.0 ( 1H, m ), 7.12 ( 1H, dd, J = 3.0, 6.2Hz ), 7.25 ( 1H, dd, J = 9.1, 9. lHz ), 8.13 ( 1H, br ), 9.86 ( 1H, br ).

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; OTSUKA PHARMACEUTICAL CO., LTD.; SHINOHARA, Tomoichi; SASAKI, Hirofumi; TAI, Kuninori; ITO, Nobuaki; WO2013/137479; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6940-78-9, name is 1-Bromo-4-chlorobutane, 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 6940-78-9, Quality Control of 1-Bromo-4-chlorobutane

In a round bottom flask, 5.0 g of 7-hydroxyquinolin-2(1H)-one, 6.42 g K2CO3 and 25 ml acetone were taken and stirred for 30 minutes at 25-35 C. 5.89 g 1-bromo-4-chloro butane was added into the reaction mixture and stirred for 5-6 hours at 50-55 C. After completion of the reaction, the reaction mixture was cooled to 25-35 C. The reaction mixture was filtered. The solvent was removed by distillation under vacuum. The solid was dried in a hot air oven at 45-50 C. to obtain 7-(4-chlorobutoxy) quinolin-2(1H)-one. Yield: 85%.

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; CADILA HEALTHCARE LIMITED; DESAI, Sanjay Jagdish; PARIHAR, Jayprakash Ajitsingh; SHAH, Alpesh Pravinchandra; (21 pag.)US2017/320862; (2017); A1;,
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, COA of Formula: C3H4Cl3NO

EXAMPLE 2 The preparation of a mixture of 1,1′-bis(tridecyloxycarbonyl)-dimethyl-2,2′-bibenzimidazoles in which each benzene ring contains a methyl group in the 5- or 6-position. 3,4-Diaminotoluene (100.8 g) was dissolved in methanol (600 cm3) at room temperature. The solution was stirred while methyl 2,2,2-trichloroacetimidate (70.6 g) was added in a manner similar to that described in Example 1. The mixture was allowed to cool and was stirred at room temperature for 36 hours, then diluted with water (1.5 dm3) and filtered. The solid was added again to water (1 dm3) stirred at room temperature and filtered. The solid was added to aqueous 2N sodium carbonate solution (1 dm3) stirred at 70 C. for 12 hours, cooled and filtered. The solid was repeatedly washed with methanol (3*500 cm3) by slurrying and filtering to leave a pale tan coloured solid. This solid was treated with activated carbon, recrystallized from boiling dimethylformamide, and dried, yielding 49 g of 5,5′-dimethyl-2,2′-bibenzimidazole. By this method the free base rather than the monohydrochloride was isolated (found Cl<0.2%). The structure was confirmed by measurement of the proton NMR spectrum using a solution in trifluoracetic acid with tetramethylsilane as internal standard. 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, Methyl 2,2,2-trichloroacetimidate, other downstream synthetic routes, hurry up and to see. Reference:
Patent; Imperial Chemical Industries PLC; US5258524; (1993); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics