Category: chlorides-buliding-blocks

Synthetic Route of 139512-70-2,Some common heterocyclic compound, 139512-70-2, name is 4-Chloro-5-fluorobenzene-1,2-diamine, molecular formula is C6H6ClFN2, 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 compound 5 (0.2 g, 1.24 mmol) and benzil 6d (0.26 g, 1.24 mmol) were weighed and dissolved in 20 mL glacial acetic acid. This mixture was refluxed for 2.5hr. The completion of reaction was monitored by TLC. The reaction mixture was cooled and poured into crushed ice. The precipitated product was filtered off and washed with cold water. The product was then purified by column chromatography using hexane: ethyl acetate as mobile phase. The pure fractions obtained were dried and concentrated to obtain white solids of product 7d. (yield 82%, m.p. 110-112 C). 1H NMR (400 MHz, CDCl3), delta ppm, 7.3381-7.2488 (m, 6H, Ar-3,4,5-H at C-2 and C-3), 7.441-7.411 (m, 4H, Ar-2,6-H at C-2 and C-3), 7.8824 (d, J = 9.28, -H at C-5), 8.1930 (d, J = 7.6, -H at C-8). 13C NMR (400 MHz, CDCl3), delta ppm, 113.66, 113.87, 125.44, 125.66, 128.38, 129.18, 129.27, 129.78, 129.81, 130.38, 138.38, 138.53, 138.46, 140.50, 140.61, 153.73, 153.76, 154.39, 156.93, 159.46. Mass (ESI), C20H12ClFN2, M+ and [M+2]+ peaks were found at 334 and 336, respectively.

The synthetic route of 139512-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Patel, Saloni B.; Patel, Bhumika D.; Pannecouque, Christophe; Bhatt, Hardik G.; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 230 – 240;,
Chloride – Wikipedia,
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Application of 202197-26-0, 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. 202197-26-0 name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, 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.

3-Chloro-4-((3-fluorobenzyl)oxy)aniline (12.58 g, 50 mmol) was added to 100 ml of toluene and stirred well.Thereafter, 0.4 g of acetic acid (as a catalyst) was added, followed by dropwise addition of triethyl orthoformate (3.8 g, at room temperature using an addition funnel.25 mmol), after the addition of the Dean-Stark apparatus, the reaction mixture was placed in an oil bath and heated to 80 C for 1 h.The ethanol was collected by a Dean-Stark apparatus; then the temperature was raised to 110 C for 2 h, and after the reaction was completed, it was cooled to room temperature and placed in an ice bath.The solid was precipitated, filtered, and the filter cake was washed with a little toluene to give (E)-N’-(3-chloro-4-((3-chlorobenzyl)oxy)phenyl)-N-(3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)carboxamidine 12.4 g, yield 93.7%. The HPLC purity was 99.14%.

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

Reference:
Patent; Yancheng Normal College; Nanjing University Of Technology Dafeng Ocean Industrial Institute; Sun Yaquan; Zong Chaoyang; Gu Huiwen; (10 pag.)CN108440420; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 51419-59-1, These common heterocyclic compound, 51419-59-1, name is p-Tolylmethanesulfonyl 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.

1.0 g of 6-amino-1-propyl-2(1H)-quinolinone and 1.2 equivalents of p-methylbenzylsulfonyl chloride were added to 20 ml of DMF, and 3 equivalents of potassium carbonate was added as an acid binding agent. The reaction was maintained at room temperature and stirred for 12-16 hours. After that, ice water was added and the mixture was extracted with ethyl acetate for three times and the organic phase was combined and dried over anhydrous sodium sulfate. The organic phase was concentrated and the crude product was subjected to silica gel column chromatography to give 1.3 g of compound 1022B with a yield of 70percent. (0326) 1HNMR (400 MHz, DMSO-d6): delta 0.95 (t, 3H), 1.62 (m, 2H), 2.27 (s, 3H), 4.18 (t, 2H), 4.42 (s, 2H), 6.60 (d, 1H), 7.12-7.17 (m, 4H), 7.40 (d, 1H), 7.45 (s, 1H), 7.55 (d, 1H), 7.83 (d, 1H) ppm; 13CNMR (100 MHz, DMSO-d6) delta 11.53, 20.99, 21.54, 43.35, 57.34, 116.08, 119.20, 121.17, 122.14, 124.01, 126.89, 129.46, 131.34, 133.02, 135.97, 138.12, 139.45, 161.12 ppm.

The synthetic route of 51419-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHANGHAI INSTITUTES FOR BIOLOGICAL SCIENCES, CHINESE ACADEMY OF SCIENCES; ZHU, Jiankang; ZHANG, Yulu; CAO, Minjie; LIU, Xue; WANG, Qiuhua; US2019/84; (2019); 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. 328-72-3, name is 3,5-Bis(trifluoromethyl)chlorobenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 3,5-Bis(trifluoromethyl)chlorobenzene

Example 13 Synthesis of Methyl 3,5-bis(trifluoromethyl)cinnamate 0.619 g (7.2 mmol) of methyl acrylate, 38.7 mg (120 mumol) of NBu4Br, 6.7 mg (30 mumol) of palladium acetate and 26.7 mg (120 mumol) of phenyldi(t-butyl)phosphine are weighed into a Schlenk vessel. 1.49 g (6 mmol) of 3,5-bis(trifluoromethyl)chlorobenzene and 1.53 ml (7.2 mmol) of dicyclohexylmethylamine and also 3.5 ml of dimethylacetamide are then added. The Schlenk vessel is placed in a heating bath at 130 C. and the contents are stirred. After 4 hours, the contents are poured into 30 ml of water and the product is extracted by shaking with t-butyl methyl ether. After drying the organic phase over MgSO4, the solvent is removed under reduced pressure and the product is isolated. Yellowish, crystalline solid, yield: 1.34 g (97% of theory).

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; Rampf, Florian; Eckert, Markus; US2003/105353; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl 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. Computed Properties of C6H3Cl3O2S

General procedure: To a mixture of corresponding 7 (150mg, 0.4mmol) in anhydrous THF (15mL) and DMF(3mL), corresponding sulfonyl chloride (0.5mmol) was added slowly at 0C and stirred at room temperature overnight. The mixture was poured into water and extracted with ethyl acetate (50mL×3). The combined organic layer was washed by saturated sodium chloride solution (40mL×3) and concentrated. The residue was purified by silica gel chromatography to afford 8a-8i.

The synthetic route of 2,6-Dichlorobenzenesulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Li; Zhang, Beichen; Zhao, Jingyun; Zhi, Yanle; Wang, Lu; Lu, Tao; Chen, Yadong; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 942 – 951;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, 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 461432-23-5, Formula: C15H14BrClO

To a solution of 4-bromo-1-chloro-2-(4-ethoxy-benzyl)-benzene (10.0 g, 30.71 mmol) in dichloromethane (40.0 mL) cooled to 0 degrees Celsius under nitrogen was added drop- wise over 30 minutes a 1 M solution of boron trichloride in dichloromethane (34 mL, 34.0 mmol). After the addition was complete, the reaction was allowed to warm to room temperature overnight (-16 hours). The reaction mixture was cooled to 0 degrees Celsius and an aqueous solution of 1 N hydrochloric acid was added. The resulting mixture was stirred for 30 minutes and then extracted using dichloromethane. The organic layer was separated and the aqueous layer was extracted two times with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The TLC showed only 50% conversion. The crude material was redissolved in dichloromethane (40 mL), cooled to 0 degrees Celsius, and a 1M solution of boron tribromide in dichloromethane (31 mL, 31 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature over the weekend (-55 hours). The reaction mixture was cooled to 0 degrees Celsius and an aqueous solution of 1 N hydrochloric acid was added dropwise. The resulting mixture was stirred for 30 minutes and then extracted usingdichloromethane. The organic layer was separated and the aqueous layer was extracted two times with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The reaction was purified by flash chromatography over silica gel using the ISCO automated chromatography unit (120 g silica gel column) and eluting with a gradient of 0 to 100% ethyl acetate in heptane. 9 g (98% yield) of the desired product obtained as a white solid.

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; PFIZER INC.; MASCITTI, Vincent; WO2011/51864; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 6940-78-9, A common heterocyclic compound, 6940-78-9, name is 1-Bromo-4-chlorobutane, molecular formula is C4H8BrCl, 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.

Compound (1) 7-hydroxy-2-quinolone (10.0 g, 62 mmol), 120 ml of ethanol and potassium carbonate (19.0 g, 138 mmol) were added in a 500ml reaction bottle .Compound (II) 1-bromo-4-chlorobutane (12.0 g, 70 mmol) was added with stirring, the temperature was raised to reflux and stirred for 2 hours. 100 ml of water and the compound (IV) 1-(benzo[b]thiophen-4-yl) piperazine hydrochloride (15.0 g, 59 mmol) were added, and the mixture was stirred under reflux for 9 hours. Part of the solvent was distilled off, cooled to 50 C, 40 ml of ethyl acetate was added and stirred for 0.5 hour, then continued to cooled down below 20 C, after filtration under reduced pressure, the filter cake was washed three times with 20 ml of ethanol, and then dried in a blast oven at 70 C for 3 hours. Brexpiprazole (Compound V) 14.5 g was obtained in a molar yield of 54%, which was substantially the same as the molar yield of 55% of the method described in Scheme 2.

The synthetic route of 6940-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hangzhou Xin Bosi Bio-pharmaceutical Co., Ltd.; Du Huanda; Ding Jiansheng; Ye Xinjie; Wang Zhenyu; Chen Yu; Wang Wanqing; Han Lu; Liu Yanhua; (8 pag.)CN105061414; (2019); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

102-49-8, name is 3,4-Dichlorobenzylamine, 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. Formula: C7H7Cl2N

Example 316 ethyl 4-[({[2-({[(3,4-dichlorophenyl)methyl]amino}carbonyl)-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl]methyl}oxy)methyl]benzoate A suspension of ethyl 5-{[({4-[(ethyloxy)carbonyl]phenyl}methyl)oxy]methyl}-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate (0.400 g, 0.961 mmol) obtained in Reference Example 158 and 1-(3,4-dichlorophenyl)methanamine (0.287 g, 1.63 mmol) in ethanol (16 mL) was stirred with heating at 80° C. for 15 hrs. The mixture was allowed to cool to room temperature and the precipitated solid was collected by filtration and washed with ethanol to give the title compound as a white powder (475 mg, 91percent). melting point: 253-254° C.

The synthetic route of 102-49-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Terauchi, Jun; Nara, Hiroshi; Oki, Hideyuki; Sato, Kenjiro; (166 pag.)US2015/329556; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 13918-92-8, The chemical industry reduces the impact on the environment during synthesis 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, I believe this compound will play a more active role in future production and life.

General procedure: To 5-(5-(5-Aminopyridin-3-yl)thiophen-2-yl)-2-methyl- isoindolin-1-one (49) (225 mg, 0.79 mmol) in dry pyridine (23 mL) under N2 at RT,was added dropwise, 2,4-difluorobenzenesulphonyl chloride (336 mg, 1.58 mmol) in CH2Cl2(3 mL) over 5 min. The suspension was heated to 45 C under N2 for 4 h., at which pointanother portion of 2,4-difluorobenzenesulphonyl chloride (169 mg, 0.79 mmol) in CH2Cl2 (2mL) was added. The whole mixture was left to stir for at 45 C under N2 for 16 h., then thesolvent removed under reduced pressure. The resulting residue was suspended in acetone (10mL), 1 M HCl (20 mL) added, and the entire mixture stirred for 10 minutes. The solid wasthen collected by filtration, washed well with 1 M HCl and water, dried, and purified bychromatography as described below. In cases where the bis-sulphonamide was also formed, a second step was introduced wherethe crude product above was treated with a 1:1 mixture of 1,4-dioxane and 2 M NaOH. Thecrude sulphonamide resulting from subsequent acidification of the reaction mixture wasisolated by filtration, washed well with water, and dried. Purification was carried out by flashcolumn chromatography (2% MeOH/CH2Cl2 as eluant), giving the title compound as a paleyellow solid (211 mg, 545).

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, 2,4-Difluorobenzene-1-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 4; (2017); p. 1050 – 1054;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6781-98-2, name is 2-Chloro-1,3-dimethylbenzene, 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. category: chlorides-buliding-blocks

General procedure: Under N2 atmosphere, KOtBu (1.3 equiv), toluene (1.0 mL), amines 5 (0.84 mmol), aryl chlorides 4 (0.7 mmol) and finally a solution of complex 3a (20?100muL, 0.01?0.05 molpercent, prepared from 0.014 mmol 3a in 4.0mL toluene) were successively added into a Schlenk reaction tube. The mixture was stirred vigorously at 110 °C for 24h. Then the solvent was removed under reduced pressure and the residue was purified by flash column chromatography (SiO2) to give the corresponding products.

The synthetic route of 6781-98-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Feng; Hu, Yuan-Yuan; Li, Di; Zhou, Quan; Lu, Jian-Mei; Tetrahedron; vol. 74; 39; (2018); p. 5683 – 5690;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics