Category: chlorides-buliding-blocks

210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, 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. Recommanded Product: 210532-25-5

3,5-Difluorobenzesulfonyl chloride (1 eq., 3.9 g, 18.4 mmol) was added portion-wise to a stirred solution of 6,6-dimethyl-3-[4-(4-methyl-piperazin-l-yl)-2-nitro-benzoylamino]- 5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-2-carboxylic acid ethyl ester dihydrochloride (10 g, 18.4 mmol) and N,N-diisopropylethylamine (6 eq., 19.3 mL, 110.4 mmol) in dry dichloromethane (100 mL) at room temperature. Stirring was continued for 4 hours. The reaction mixture was diluted with dichloromethane (100 mL) then washed with saturated sodium hydrogenocarbonate (150 mL), dried over sodium sulfate, evaporated to dryness and purified by flash chromatography on silica gel, using acetone as eluant. The title compound was obtained as yellow solid (9 g, 65% yield). IH-NMR (400 MHz), delta (ppm, DMSOtZ6): 10.71 (s, IH), 7.69-7.62 (m, 4H), 7.47 (d, J2=2.44 Hz, IH), 7.29 (dd, Jl=9.03 Hz, J2=2.44 Hz, IH), 4.58 (s, 2H), 4.43 (q, J=7.07 Hz, 2H), 3.41 (m, 4H), 2.50 (m, 4H), 2.26 (s, 3H), 1.67 (s, 6H), 1.35 (t, J=7.07 Hz, 3H).

The synthetic route of 210532-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; WO2007/68637; (2007); A1;,
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Application of 39226-95-4, A common heterocyclic compound, 39226-95-4, name is 2,3-Dichlorobenzylamine, molecular formula is C7H7Cl2N, 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: Under nitrogen atmosphere, a Schlenk tube was sequentially charged with cyclicdiaryliodonium salt (1.0 equiv), copper catalyst A1 or A2 (5.0 mol%), Na2CO3 (3.0 equiv) anddichloromethane (0.05 M). After the mixture was chilled to proper temperature, the appropriateamine (1.2 equiv) was added and stirred for the time indicated in the experimental procedures.The reaction mixture was filtered through a plug of celite with ethyl acetate. The filtrate wasconcentrated under reduced pressure, and the residue was purified by column chromatographyon silica gel to deliver the corresponding product.

The synthetic route of 39226-95-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Kun; Duan, Longhui; Xu, Shibo; Jiang, Julong; Fu, Yao; Gu, Zhenhua; Chem; vol. 4; 3; (2018); p. 599 – 612;,
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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 the 20 cc THF and 20 cc Toluene added 0.25 mole 2-ehloro-5-bromo-4′- ethoxydiphenylmethane under argon atmosphere. Cooled the reaction mass to – 78 C. Slowly added n-Butyl lithium (1.9 M in hexane) at – 78 C and stirred for 30 min. Slowly added 20 % Ammonium chloride solution to the reaction mass. Brought the reaction mass to ambient temperature and stirred for 30 min. Settled and separated layers. Extracted the aqueous layer with 50 cc toluene. Washed the combined organic layer with 500 cc brine solution. Distilled out the toluene and charged heptanes, stirred for 2 – 3 hrs at ambient temperature. Filtered the product and dried the product at 45 – 50C under reduced pressure to get 93 % titled compound. Mass: (m+1) 247 m/z found 247.1 1 HPLC purity: 96.33 %

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; HARMAN FINOCHEM LIMITED; KADAM, Vijay Trimbak; SAIKRISHNA; CHOUDHARE, Tukaram Sarjerao; MINHAS, Harpreet Singh; MINHAS, Gurpreet Singh; (26 pag.)WO2016/147197; (2016); A1;,
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Electric Literature of 6579-54-0, 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. 6579-54-0 name is 2,6-Dichlorobenzenesulfonyl chloride, 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.

General procedure: A solution of the appropriate acid halide fragments (4.8 mmol)in dry pyridine (5 mL) was dropwise added to a well-stirredmixture of the intermediate 3-amino-substituted rutaecarpine 5(4 mmol) in dry pyridine (50 mL) at room temperature. The reactionwasstirred for 30 min and monitored by TLC. After the reactioncompleted, the pH was adjusted to neutral with dilute hydrochloricacid. The pyridine and residual sulfonyl chloride were distilledunder reduced pressure. The mixture was extracted with an ethylacetate-water system. The aqueous layer was discarded and ethyl acetate was evaporated to obtain crude product. The crude productwas washed with water and dried under vacuum. The solid residuewas purified by flash chromatography on silica gel with ethyl acetate/petroleum ether (1:1) elution to provide the desired derivatives6a-6p, 7a-7c, and 8a.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dichlorobenzenesulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Article; Wu, Mingfei; Ma, Jie; Ji, Lijun; Wang, Min; Han, Jianfei; Li, Zeng; European Journal of Medicinal Chemistry; vol. 177; (2019); p. 198 – 211;,
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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. 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, This compound has unique chemical properties. The synthetic route is as follows., name: 5-(Chloromethyl)benzo[d][1,3]dioxole

Preparation of 1, 3-benzodioxol-5-ylmethyl isopropyl sulfone 7.8 g of 5-(chloromethyl)-1, 3-benzodioxol was dissolved in 20 ml of anhydrous tetrahydrofuran and 20 ml of diethyl ether and then added to magnesium at 0C, and reacted for 10 minutes. The reactant was heated to 50C and reacted for 1 hour. The reaction mixture was cooled to 0C and then slowly added to a flask containing [1, 3-bis (diphenylphosphino) propane] nickel (II) dichloride as a catalyst. After the addition of 3. 9 ml isopropane sulfonyl chloride, the mixture was reacted for 30 minutes and the reactant was heated to 50C and reacted for 1 hour. Then, its pH was adjusted to 7 with dilute hydrochloric acid. The resulting mixture was extracted with diethyl ether and distilled water, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was fractionated by column chromatography using ethyl acetate: n-hexane (1: 3), to give 0.6 g of the title compound of the following formula ld (Rf : 0.35, Yield: 5%). [Chemical Formula 1d] The compound was dissolved in CDC13 and TMS and then characterized by IH NMR spectroscopy. The result is as follows ; ‘H NMR 8 : 1.60-1. 62 (d, 6H, J=6.7Hz), 2.79 (s, 2H), 3.75-3. 78 (m, 1H), 5.91 (s, 2H), 6.66 (m, 3H)

According to the analysis of related databases, 20850-43-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HAN, Sang Min; LEE, Myung Hee; CHOI, Won Chul; WO2005/70915; (2005); A1;,
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Application of 918538-05-3, 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. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

j00535j Compound rac**A2 (50 mg, 0.3 mmol) and 2,4-dichloropyrrolo[2,1-JI[1,2,4jtriazine (52 mg, 0.3 mmol) were dissolved in 2-propanol (1 mL). After stirring at room temperature for 3 hours, N,N-diisopropylethylamine (80 .iL, 0.5 mmol) was added, and the reaction mixture was stirred for 16 hours, concentrated onto silica and purified by column chromatography [chloroform: 7M NH3 in methanol = 1:0 to 9:11 to afford compound rac-6-int (59 mg, 64% yield). LCMS (1): tR=2.498 mi, (ES) m/z (M+H) = 333.0.

The synthetic route of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); A1;,
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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. 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Chloro-4-((3-fluorobenzyl)oxy)aniline

(iii) Preparation of N-[3-chIoro-4-[(3-fluorobenzyIoxy)phenyl]-6-iodo- quinazolin amine (3) Into a one liter four-necked round bottomed flask, 500mL of acetic acid, 50.0 g of N’- (2-cyano-4-iodo-phenyl)-N, N-dimethyl formamidine of the formula-(8) obtained according to the process given in the above step (ii) 51.0 g 3-chloro-4-(3′- fluorobenzyloxy)aniline were charged . The reaction mass was maintained at 115- 120 C for about 2 Hrs., the cooled to 25-35 C and quenched into ice cold water. The pH of the reaction mass was adjusted to basic by slow addition of aqueous ammonia solution and the reaction mass was filtered and dried at 70-75 C.Dry weight: 93.0 gPurity: 83.64% by HPLCThe purity of the product is enhanced by adopting the following procedure.

According to the analysis of related databases, 202197-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NATCO PHARMA LIMITED; JYOTHI PRASAD, Ramanadham; ADIBHATLA KALI SATYA, Bhujanga rao; VENKAIAH CHOWDARY, Nannapaneni; WO2011/39759; (2011); A1;,
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Application of 1871-57-4,Some common heterocyclic compound, 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, molecular formula is C4H6Cl2, 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.

To a suspension of sodium hydride (purity> 55%, 11.4 g) in N, N-dimethylformamide (150 mL),Under ice cooling, add 3-chloro-2-chloromethyl-1-propene (12.7 mL, CAS number: 1871-57-4),After stirring for 10 minutes at the same temperature,2- (tert-Butoxycarbonylamino) -1-ethanolA solution of (19.3 g, CAS number: 26690-80-2) in tetrahydrofuran (150 mL) was added dropwise over one and a half hours, and the mixture was stirred at room temperature for two and a half hours.The reaction solution was ice-cooled, water was added, and the mixture was extracted 3 times with diethyl ether,The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate.After filtration and concentration under reduced pressure, the obtained residue is purified by silica gel column chromatography (n-hexane / ethyl acetate) to give the title compound.(16.0 g) was obtained as an oil.

The synthetic route of 1871-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Healthcare Co Ltd; Naito, Hiroyuki; Suzuki, Takayuki; Murata, Takeshi; Kawai, Junya; Higuchi, Saito; (99 pag.)JP2020/45306; (2020); A;,
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Synthetic Route of 367-22-6, 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. 367-22-6, name is 4-Chloro-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

4.1.1 Ethyl 2-((4-chloro-3-fluorophenyl)amino)-2-oxoacetate (6a) To a stirred solution of 3-fluoroaniline (1.11 g, 10.0 mmol) in CHCl3 (30.0 mL) was added dropwise N-chlorosuccinimide (NCS) in CHCl3 (20.0 mL) at 0 C. The mixture was stirred at 0 C for 42 h. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in Et2O. The mixture was washed with water, and dried over MgSO4. Concentration under reduced pressure followed by flash chromatography over silica gel with EtOAc/n-hexane gave 4-chloro-3-fluoroaniline (259.4 g, 18% yield) as crystalline solids. To a stirred solution of the above aniline (259.4 mg, 1.78 mmol) in THF (8.9 mL) were added at 0 C ethyl chloroglyoxylate (237.3 muL, 2.14 mmol) and Et3N (296.6 muL, 2.14 mmol). The mixture was stirred at room temperature for 12 h. After the precipitate was filtrated off, the filtrate solution was concentrated under reduced pressure. The residue was dissolved in EtOAc, and washed with 1.0 M HCl, saturated NaHCO3 and brine, then dried over MgSO4. Concentration under reduced pressure to provide the title compound 6a (435.2 mg, 99% yield) as brown crystals, which was used without further purification. 1H NMR (500 MHz, CDCl3) delta 1.44 (t, J = 7.50 Hz, 3H), 4.43 (q, J = 7.50 Hz, 2H), 7.24-7.25 (m, 1H), 7.35-7.40 (m, 1H), 7.70-7.75 (m, 1H), 8.93 (br, 1H); 13C NMR (125 MHz, CDCl3) delta 13.0, 64.1, 108.5 (d, J = 26.3 Hz), 115.9 (d, J = 3.75 Hz), 117.3 (d, J = 18.8 Hz), 130.9 (d, J = 10.0 Hz), 135.9, 153.9, 158.1 (d, J = 246.3 Hz), 160.5; HRMS (ESI), m/z calcd for C10H10ClFNO3 (MH-) 244.0182, found 244.0183.

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-3-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Narumi, Tetsuo; Arai, Hiroshi; Yoshimura, Kazuhisa; Harada, Shigeyoshi; Hirota, Yuki; Ohashi, Nami; Hashimoto, Chie; Nomura, Wataru; Matsushita, Shuzo; Tamamura, Hirokazu; Bioorganic and Medicinal Chemistry; vol. 21; 9; (2013); p. 2518 – 2526;,
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Related Products of 2533-69-9,Some common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, molecular formula is C3H4Cl3NO, 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.

To a solution of 3-bromo-4-chlorobenzene-1,2-diamine (4 g, 18 mmol) in AcOH ( 30 mL) was added methyl 2,2,2-trichloroacetimidate (3.5 g, 20 mmol) drop wise at 0 C. Then the reaction mixture was stirred at room temperature overnight. The mixture was poured into water (200 mL), and precipitate was collected and dried to give 4-bromo-5-chloro-2-(trichloromethyl)-1H-benzo[djimidazole (5.5 g, 80%) as a white solid. HPLC/UV purity: 95%; LC-MS (ESI): 349.1 (M + 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2,2,2-trichloroacetimidate, its application will become more common.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; PINKERTON, Anthony B.; ARDECKY, Robert J.; ZOU, Jiwen; (256 pag.)WO2018/204176; (2018); A1;,
Chloride – Wikipedia,
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