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. 106-39-8, name is 1-Bromo-4-chlorobenzene, A new synthetic method of this compound is introduced below., COA of Formula: C6H4BrCl

General procedure: To a mixture of aryl halide (0.3 mmol), NiCl2(H2O)1.5 [1] (0.0075 mmol, 2.5 mol percent), was charged dry THF (1 mL). The mixture was pumped and refilled with nitrogen for three times. The resulting mixture was stirred at -10 under nitrogen for 30 min. The reaction mixture was quenched through the addition of ice MeOH, then poured into a separatory funnel containing saturated aqueous NH4Cl (ca. 5 mL) and extracted with EtOAc (3 x 5 mL). The combined organic layers were washed with brine and dried over Na2SO4. The crude product was purified by column chromatography. Extent of isomerization can be easily determined via 1H NMR spectroscopy by comparison of the intergral of the singlet from the t-butyl group (1.3-1.4 ppm, 9H) to the integral of the doublet from the benzylic S3 protons of the i-butyl group (2.4-2.5 ppm, 2H). The doublet from the methyls of the i-butyl group could additionally be used (ca. 0.8 ppm, 6H).

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:
Article; Wu, Zhenghan; Si, Tengda; Xu, Guangqing; Xu, Bin; Tang, Wenjun; Chinese Chemical Letters; vol. 30; 3; (2019); p. 597 – 600;,
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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 1939-99-7 as follows. HPLC of Formula: C7H7ClO2S

A stirred solution of ethyl(3-amino-2-oxo-1,2-dihydropyridyl)acetate (40.0 g, 0.204 mole) and 2,4,6-collidine (54 ML, 0.408 mole) in tetrahydrofuran (200 ML) was cooled in an ice bath.. A solution of benzylsulfonyl chloride (38.9 g, 0.204 mmole) in tetrahydrofuran (200 ML) was added over a 50-minute period.. After addition was complete, the solution was stirred for 30 minutes at 0 C. The reaction mixture was diluted with ethyl acetate (1.2 L), washed with 1.0N HCl (until aqueous layer is PH 1), water (50 ML), saturated sodium bicarbonate (100 ML), and brine (2*50 ML).. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed.. The residue was recrystallized from chloroform. 39 g of the title compound was isolated.. To the mother liquor was added silica gel.. The solution was swirled, then filtered through a sintered glass funnel, washing with 50% ethyl acetate in dichloromethane.. The solvent was removed from the filtrate, and the residue was recrystallized from chloroform.. An additional 13 g of the title compound was isolated to afford a total of 52.00 g (75% yield) of the title compound as a tan solid. Rf=0.32 (silica gel, 20% ethyl acetate in dichloromethane); m.p. 48-49 C.

According to the analysis of related databases, 1939-99-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Corvas International, Inc.; US6342504; (2002); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 51419-59-1,Some common heterocyclic compound, 51419-59-1, name is p-Tolylmethanesulfonyl chloride, molecular formula is C8H9ClO2S, 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: Sodium hydride (60percent dispersion in mineral oil) (18 mg, 0.45 mmol) was added to a solution of 2-(4-(Piperazine-1-carbonyl)phenyl)quinazolin-4(3H)-one (4) (50 mg, 0.15 mmol) in DMF (10 mL), and the mixture was heated at 100 °C. Appropriate sulfonyl chloride (0.22 mmol) in DMF (3 mL) was added slowly to the reaction mixture. The mixture was stirred at 100 °C for 16 h. After cooling, saturated NaHCO3 solution was added. The reaction mixture was extracted with ethyl acetate and the organic phase was washed with brine. The organic phase was dried over MgSO4 and evaporated in vacuo. The residue was washed with ethyl acetate/hexane (1:10) and purified by column chromatography (ethyl acetate) to provide 2-(4-(4-(substituted)-sulfonyl)piperazine-1-carbonyl)phenyl)quinazolin-4(3H)-one.

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

Reference:
Article; Rhee, Hee-Kyung; Yoo, Ji Hye; Lee, Eunyoung; Kwon, Young Joo; Seo, Hang-Rhan; Lee, Yun-Sil; Choo, Hea-Young Park; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 3900 – 3908;,
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Related Products of 1716-42-3, 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. 1716-42-3, name is 1-(3-Chloropropoxy)-4-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 14 N-Methyl-N-(4-(4-(1-(3-(4-fluorophenoxy)propyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)-2-(3,4-dichlorophenyl)butyl)benzamide STR38 14.1 Synthesis of N-methyl-N-(4-(4-(1-(3-(4-fluorophenoxy)propyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl) -2-(3,4-dichlorophenyl)butyl)benzamide Combine N-methyl-N-(4-(4-(1H-benzimidazol-2-yl-amino)piperidin-1-yl)-2-(3,4-dichlorophenyl)butyl)benzamide (0.78 mmol), 1-chloro-3-(4-fluorophenoxy)propane (0.15 g, 0.78 mmol), benzyltriethylarnmonium chloride (0.01 g), sodium hydroxide (2.0 g), water (2 mL), and dichloromethane (4 mL). Heat to about 35° C. After 18 hours, add ethyl acetate (100 mL) and separate the layers. Extract the organic layer with aqueous saturated sodium bicarbonate and brine. Dry the organic layer over Na2 SO4, filter, and evaporate in vacuo to give the title compound.

The chemical industry reduces the impact on the environment during synthesis 1-(3-Chloropropoxy)-4-fluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hoechst Marion Roussel, Inc.; US5922737; (1999); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 13745-86-3,Some common heterocyclic compound, 13745-86-3, name is 11-Chlorodibenzo[b,f][1,4]thiazepine, molecular formula is C13H8ClNS, 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.

(b) 11-Piperazinyl-dibenzo[b,f][1,4]thiazepine. Piperazine (1.7 mole) was dissolved in warm toluene (about 50C) (750 ml) and 11-chloro-dibenzo[b,f][1,4]thiazepine added. The reaction was heated to reflux and maintained at this temperature for 5 hr. After cooling to ambient temperature the reaction was filtered to remove piperazine hydrochloride, the organic phase was washed several times with water to remove excess piperazine. The organic phase was dried over magnesium sulphate and after filtration the solvent was removed in vacuo to give the product as an oil. The oil was dissolved in ethanol and treated with a solution of hydrogen chloride in ethanol. 11-Piperazinyl-dibenzo[b,f][1,4]thiazepine was isolated as the dihydrochloride salt in ca 88% yield, m.pt. 103-105 (softens), 135-140C (decomp).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 11-Chlorodibenzo[b,f][1,4]thiazepine, its application will become more common.

Reference:
Patent; IMPERIAL CHEMICAL INDUSTRIES PLC; EP282236; (1988); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 38762-41-3, 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 38762-41-3 as follows.

To a solution of 4-bromo-2-chloro-phenylamine (32 g, 0.15 mol) and pyridine (13.45 g, 0.17 mol) in DCM (200 mL) was added 3-chloropropionyl chloride (21.65 g, 0.17 mol) dropwise at 15 C. After stirring at room temperature for 1 hour, the mixture was washed with water and then aqueous 2N HC1. The organic layer was dried over anhy. Na2S04, filtered, and concentrated in vacuo to afford title compound (10.9 g, 90%) as a white solid.

According to the analysis of related databases, 38762-41-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; HORNSPERGER, Benoit; KUHN, Bernd; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; (77 pag.)WO2016/66597; (2016); A1;,
Chloride – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1205-71-6, name is 4-Chloro-N-phenylaniline, 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 1205-71-6, Recommanded Product: 1205-71-6

General procedure: To a 50 mL of two-neck round-bottomed flask charged with a magnetic stirrer bar, were successively added 1-Bromo(2-diphenylphosphoryl)ethyne (1) (305 mg, 1.0 mmol), diphenylamine(203 mg, 1.2 mmol, 1.2 equiv), K3PO4 (637 mg, 3.0 mmol, 3.0 equiv) and dehydrated toluene (5mL). After the mixture was stirred at 80 C for 15 h, the reaction mixture was quenched with 1 mL of saturated NH4Cl aq., and extracted with ethyl acetate and H2O, and dried over brine and MgSO4. The crude product was purified by flash chromatography (hexane/EtOAc, 1:2) to afford the corresponding phosphoryl ynamine 2a (240 mg) in 61% yield.

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:
Article; Okuda, Yasuhiro; Seo, Tomoyo; Shigezane, Yuki; Watanabe, Hikaru; Akashi, Haruo; Iwanaga, Tetsuo; Orita, Akihiro; Chemistry Letters; vol. 48; 12; (2019); p. 1484 – 1487;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 3460-24-0, These common heterocyclic compound, 3460-24-0, name is 1,4-Dibromo-2-chlorobenzene, 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.

1,4-Dibromo-2-Chloro-Benzene 1eq(45.8 g), 2-aminophenylboronic acid 2eq (46.5 g), Pd (PPh3) 4 5 mol% (9.8 g) and K2CO3 2eq (46.9 g) were dissolved in toluene 1-fold, 550 ml) and distilled water (5 times as much as K2CO3, 235 ml), and the mixture was stirred under reflux for 18 hours under a nitrogen stream. After completion of the reaction, the reaction mixture was extracted with toluene and distilled water. The organic layer was dried with magnesium sulfate (MgSO4) and filtered, and the filtrate was concentrated under reduced pressure. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v), and the resulting solid was recrystallized from dichloromethane and acetone to obtain intermediate d-1 (23.5 g, Y = 47%).

The synthetic route of 3460-24-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung SDI Co., Ltd; Jang Gi-po; Kim Jun-seok; Lee Seung-jae; Hong Jin-seok; Kim Chang-u; Jeong Seong-hyeon; Kim Yeong-gwon; Ryu Eun-seon; Jeong Ho-guk; (30 pag.)KR2017/111538; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 1435-48-9, name is 2,4-Dichloro-1-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 1435-48-9, HPLC of Formula: C6H3Cl2F

[209] Alternate preparation: To a solution of 2,4-dichloro-1-fluorobenzene (100 g, 0.606 mol) in THF (1.4 L) under nitrogen at -78 C, was added a 2.5 M solution of n-BuLi in hexanes (267 ml_, 0.666 mol) dropwise over a period of 30 min, maintaining the temperature between -70 to -78 C. After 1.5 h stirring at -78 C, methyl formate (72.6 ml_, 1.21 mol) was added slowly, and the reaction mixture was stirred overnight, warming up to rt. The reaction was quenched with sat. aqueous NH4CI (200 ml.) and the organic layer was separated. The organic solvents were removed by distillation at atmosphere pressure and the crude material which contained a small amount of THF was crystallized from hexanes to give the title compound.

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; OSI PHARMACEUTICALS, INC.; CHEN, Xin; JIN, Meizhong; KLEINBERG, Andrew; LI, An-hu; MULVIHILL, Mark, J.; STEINIG, Arno, G.; WANG, Jing; WO2010/59771; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 108047-39-8, These common heterocyclic compound, 108047-39-8, name is 2-(Aminomethyl)-4-chloroaniline, 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.

A solution of the amine of preparation 10 (6. 4 g, 41 MMOL) in tetrahydrofuran (50 ML) was added to a solution of the oxadiazole of preparation 5 (4.56 g, 16 MMOL) in tetrahydrofuran (50 ML) and the mixture was heated to 50 C for 18 hours. The reaction mixture was evaporated under reduced pressure and the residue was purified by chromatography on silica gel using methanol in DICHLOROMETHANE as eluant (5: 95), to give the title compound as a white solid (4.65 g). APCI MS M/Z 399 [MH] + ‘H NMR (400MHZ, CDCI3) : 8 1.95 (m, 2H), 2.20 (m, 2H), 3.10 (m, 2H), 3.20 (m, 1H), 3.80 (s, 2H), 4.00 (s, 2H), 4.30 (m, 2H), 6.60 (m, 1H), 6.65 (t, 1H), 6.70 (d, 1H), 7.00 (s, 1H), 7.05 (d, 1H), 7.50 (t, 1H), 8.20 (d, 1H)

The synthetic route of 108047-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/74291; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics