Month: September 2021

Some common heterocyclic compound, 699-89-8, name is 4,7-Dichlorothieno[2,3-d]pyridazine, molecular formula is C6H2Cl2N2S, 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. name: 4,7-Dichlorothieno[2,3-d]pyridazine

A 250 mL, round-bottomed flask was equipped with a stir bar and reflux condenser. To the flask was added the product of step 4 (7.65 g, 37.3 mmol), 4-chloroaniline (4.76, 37.3 mmol) in EtOH (75 mL). The mixture was refluxed for 3 h. An orange solid precipitated from the reaction after 3 h. The reaction was cooled to rt and the solid was collected by filtration and washed with hexane. The desired 7-chloro-4-(4-chlorophenylamino)thieno[2,3-d]pyridazine was obtained (6.5 g, 21.9 mmol; 60% yield); mp=139-142 C.; ES MS (M+H)+=297; TLC (Hexane-EtOAc, 60:40); Rf=0.48.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 699-89-8, its application will become more common.

Reference:
Patent; Bayer Pharmaceuticals Corporation; US6689883; (2004); B1;,
Chloride – Wikipedia,
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These common heterocyclic compound, 67952-93-6, name is 3-Chloro-4-methylbenzylamine, 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. SDS of cas: 67952-93-6

General procedure: A mixture of 2-amino-3-nitrobenzoic acid (5.0 mmol), EDCI (6.0 mmol),and HOBt (0.6 mmol) in DCM (30 mL) was stirred at room temperature for 5 mins. Then, amines (6.0 mmol) were added and the reaction was stirred at room temperature overnight. After completion, the mixture was diluted with DCM, washed with water twice, dried over anhydrous Na2SO4, evaporated, and chromatographed (EtOAc – petroleum ether) to afford the compounds 2a-k.

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

Reference:
Article; Chen, Yinbo; Le, Vanminh; Xu, Xiaoyong; Shao, Xusheng; Liu, Jianwen; Li, Zhong; Bioorganic and Medicinal Chemistry Letters; vol. 24; 16; (2014); p. 3948 – 3951;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 202925-08-4, name is 1-Chloro-3-fluoro-5-methoxybenzene, 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. Application In Synthesis of 1-Chloro-3-fluoro-5-methoxybenzene

A mixture of aluminum chloride (2.50 g, 18.7 mmol) and acetyl chloride (1.30 rnL, 18.7 mmol) in CH2Cl2 (10.0 mL) was stirred at 0 C for 30 min. The reaction mixture was slowly added with 1-chloro-3-fluoro-5-methoxybenzene (13-1, 1.00 g, 6.23 mmol) in CH2Cl2 (5.0 mL). The solution was stirred at room temperature for additional 2.0 h. The solution was bsified with saturated aqueous NaHCO3, and the organic layer was separated,dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give a mixture of 1-(2-chloro-6-fluoro-4-methoxyphenyl)ethanone (13-2) and 1-(2-chloro-4-fluoro-6-methoxyphenyl)ethanone (13-3) as yellow oil in 1.2 g (5.9 mmol) total weight (95% yield).

The synthetic route of 1-Chloro-3-fluoro-5-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAIVEX THERAPEUTICS CORPORATION; HUANG, Yu-Ling; CHUANG, Shih-Hsien; LEE, Ying-Shuan Eda; HUANG, Jiann-Jyh; LAU, Johnson; WO2013/82324; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13078-79-0, name is 2-(3-Chlorophenyl)ethanamine, 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 13078-79-0, Safety of 2-(3-Chlorophenyl)ethanamine

GammaAlpha1 r2-(3-Chloro-phenyl)-ethyll-carbamic acid methyl ester At 0 C, methyl chloroformate (4.6 g, 48 mmol) was added drop wise to a solution of 2-(3- chloro-phenyl)-ethylamine (5.0 g, 32 mmol) and Et3N (6.4 g, 64 mmol) in DCM (100 mL). After the addition, the mixture was stirred at room temperature for 0.5 hours. The organic layer was washed with water (3 x 30 mL), IN HCl (20 mL) and brine (30 mL), dried over anhy. Na2S04, filtered and concentrated in vacuo. After vacuum drying, the title compound was obtained (6.49 g, 95%) as a white solid. MS: 214.1 (M+H)+.

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-(3-Chlorophenyl)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt E.; CHEN, Junli; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; LI, Dongbo; MAERKI, Hans Peter; MARTIN, Rainer E.; MAYWEG, Alexander; TAN, Xuefei; WU, Jun; YU, Jianhua; (109 pag.)WO2016/55394; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 53145-38-3, 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. 53145-38-3, name is 2-Chloro-6-fluoroanisole belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

100ml three-neck eggplant flask fully dried2- (4,4,5,5-tetramethyl-1,3,2-dioxabolan-2-yl) aniline (manufactured by Tokyo Chemical Industry Co., Ltd.) (with condenser, three-way cock and magnetic stir bar)2.41 g (11 mmol),1.61 g (10 mmol) of 2-chloro-6-fluoroanisole,1,3-bis- (2,6-diisopropylphenyl) imidazolium- (allyl) -palladium (II) -chloride(Sigma Aldrich Japan Co., Ltd.)0.029 g (0.05 mmol),Barium hydroxide octahydrate (manufactured by Wako Pure Chemical Industries, Ltd.)4.73 g (15 mmol) was added,Dissolved in 50 mL of isopropyl alcohol,The reaction was performed at 80 C. for 6 hours.After the reaction, the solid residue is removed by filtration,The solvent was distilled off under reduced pressure to obtain a crude product.Crude product is silica gel column chromatograph(Eluent; hexane / ethyl acetate = 9/1)1.37 g (63%, white solid) was obtained.

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-Chloro-6-fluoroanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mitsui Chemical Inc; Hanada, Shiori; Kinoshita, Shinsuke; Kawamura, Noromori; Muroto, Toshihiro; Tanaka, Kenichi; Ishii, Seiichi; Terao, Hiroshi; Saito, Yasunori; Hara, Retsu; Mizobuchi, Yusuke; (67 pag.)JP5769444; (2015); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 108-37-2, A common heterocyclic compound, 108-37-2, name is 1-Bromo-3-chlorobenzene, molecular formula is C6H4BrCl, 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.

This example illustrates the tandem Ir-catalyzed borylation and catalytic amination process. [0064] 3-Aminoboronic acids and esters as shown below are of interest as evidenced by the large number of derivatives synthesized, and by several patents, which note their activity as O-lactamase inhibitors (See, for example, Shoichet et al., WO0035905). Few in number, however, are 1, 3, 5-aminoboronic acids and esters (about 25 compounds by SCIFINDER SCHOLAR). Such substrates may prove useful for further derivatization as they can possess three unique sites for diversity. Furthermore, these compounds may prove ideal as scaffolds for combinatorial libraries. The boronic acid or ester can be transformed into a myriad of functionalities including aryl or vinyl via the Suzuki-Miyuara coupling (Miyaura and Suzuki, Chem. Rev. 95: 2457-2483 (1995); Suzuki, J. Organomet. Chem. 576: 147-168 (1999); Miyaura, In Advances in Metal-Organic Chemistry: Liebeskind, Ed.: JAI: London,; Vol. 6, pp. 187-243 (1998)). If R is a halogen, then there exists a multitude of coupling opportunities (See, for examples, Metal-catalyzed Cross-coupling Reactions; Diederich and Stang, eds.: Wiley: Wienheim, 1998). [0066] Recently, a catalytic aromatic C-H activation/borylation reaction utilizing Ir- or Rh-catalysts was developed. The process is high yielding, functional group tolerant (alkyl, halo, carboxy, alkoxy, and protected amino), chemoselective (1,3-substited arenes give only the 5-boryl product), and efficient (Iverson and Smith, J. Am. Chem. Soc. 121: 7696-7697 (1999); Cho et al., J. Am. Chem. Soc. 122: 12868-12869 (2000); Tse et al., Org. Lett. 3: 2831 (2001); Chao et al., Science 295: 305-308 (2002)). Furthermore, the process allows for the direct construction of aryl boronic esters from hydrocarbon feedstocks without going through an aryl halide. Scheme 2 depicts a prototypical borylation reaction: borylation of benzene using (Ind)Ir(COD)(2 mol %), dppe (2 mol %). The borane of choice is pinacolborane (HBPin). A variety of Ir(I) catalysts can be used, including [Ir(COD)Cl]2, Ir(Indenyl)(C2H4)2, Ir(Indenyl)dppe, and (Indenyl)Ir(COD), in the presence of 2 mol equivalents of PMe3 or 1 mol equivalent of a bidentate ligand like dmpe or dppe. The catalyst system of choice is (Indenyl)Ir(COD), dppe or dmpe (2 mol % each) because of it’s cleanness of reaction and efficient TOF (24 h-1 with benzene). The reaction can be run in the neat arene or in inert solvents (e.g. cyclohexane). During our studies into tandem borylation/Suzuki coupling, we noted difficulties with the hydrolysis of the boronic ester functionality (Bpin). The robustness of the BPin group suggested that, perhaps, the pinacol might serve as a protecting group for the boron. Thus, it was deemed of interest to explore other catalytic transformations in the presence of the BPin group. One such transformation is the Buchwald-Hartwig amination of aryl halides (See, for example; Wolfe et al.,. J. Org. Chem. 65: 1158 (2000); Hartwig et al., J. Org. Chem. 64: 5575 (1999); Wolfe and Buchwald, Angew. Chem. Int. Ed. 38: 2413 (1999)). Initially, the reaction was attempted on pure 1-chloro-3-methylphenyl-5-BPin. As shown in Scheme 3 (Buchwald-Hartwig coupling of 1-chloro-3-methylphenyl-5-BPin with aniline), application of Buchwalds protocol proceeded cleanly to give the desired cross-coupling product in 64.7% and 63.8% yield. The use of PtBu3 improved the yield to 78.8%. Unfortunately, initial attempts to perform the reaction in the ?one-pot? protocol were unsuccessful. Table 1 summarizes the results. In all cases where K3PO4.nH2O was used, a significant amount of pinacol was observed by GC-FID (Entries 1-5). While this is indicative of reaction of the BPin group and is most likely a by-product of Suzuki coupling (in this case, dimerization or oligiomerization of the starting material), no dimers or oligiomers were isolated. Noteworthy, is the formation of the desired product, albeit in low yield (10% GC-FID ratio), using K3PO4.nH2O and PtBu3 when all other attempts using the base failed. With anhydrous K3PO4, results were better (Entries 6-9). Most importantly, no pinacol was formed in these reactions. Changing the base or increasing catalyst loading did not improve the results. The use of PtBu3 led to the best results and after 4 days at 100 C., 34.4% of the desired product was isolated (Entry 10). This result, however, falls short of the reaction performed on pure material and shows that the by-products from the Ir-catalyzed borylation are not completely innocuous. As was previously mentioned, a potential source of concern is the presence of free bidentate phosphines after the borylation, which may interfere with subsequent reactions. In the tandem Suzuki reactions, an aryl chloride was successfully coupled only when dmpe was used as the Ir ligand. Thus, the tandem borylation/Buchwald-Hartwig amination reaction of the present invention was attempted using the (Ind)Ir(COD)/dmpe precatalyst….

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; Board of Trustees of Michigan State University; US2004/24237; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 7149-75-9, 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 7149-75-9 as follows.

Step 1 (0415) To a mixture of 4-chloro-3-methylphenylamine (300 mg), acetone (0.19 mL) and methanol (10 mL) was added decaborane (130 mg), and the mixture was stirred at room temperature for 6 hours. After the mixture was diluted with ethyl acetate, to the resulting mixture was added aminopropyl silica gel powder (3 g). The resulting mixture was filtered and the filtrate was concentrated under reduced pressure to give (4-chloro-3-methylphenyl)(isopropyl)amine (390 mg).

According to the analysis of related databases, 7149-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; Inoue, Hitoshi; Ohno, Kohsuke; Nakamura, Tetsuya; Ohsawa, Yusuke; (58 pag.)US2016/362368; (2016); 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. 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, A new synthetic method of this compound is introduced below., Formula: C6H3BrClF

A 100 mL 3 -neck flask was placed under N2 and equipped with a condenser and an addition funnel. Magnesium (2.0 g, 83 mmol) were added, bromo-3-chloro- 5-fluoro benzene (15 g, 72.5 mmol) was taken up in dry THF (70 mL), and transferred to the addition funnel. The Grignard reaction was initiated with approximately 2 mL of the bromo-3-chloro -5-fluorobenzene solution and iodine. The remaining bromo-3-chloro-5-fluorobenzene solution was added and the reaction was refluxed 1 hour.

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; VITAE PHARMACEUTICALS, INC.; WO2008/156817; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 6579-54-0, The chemical industry reduces the impact on the environment during synthesis 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, I believe this compound will play a more active role in future production and life.

Synthesis Example 26 Synthesis of 2,6-Dichlorobenzenesulfonamide [Compound (III-7)] To a solution obtained by dissolving 29% aqueous ammonia (6.9 g, 20.36*5 mmol) in 40 ml of acetonitrile was added dropwise a solution of 2,6-dichlorobenzenesulfonyl chloride [Compound (XXII-7)] (5 g, 20.36 mmol) in 10 ml of acetonitrile under cooling with water. Thereafter, the reaction solution was stirred at room temperature for 3 hours and distilled off. Water was added to the residue, followed by filtration to obtain an insoluble material, which was washed with water and then with a small amount of acetonitrile. White solid, m.p.; 173-5 C., yield: 4.3 g, percent yield: 94%. IR KBr cm-1: 3382, 3268, 1575, 1428, 1338, 1143, 780. 1H-NMR (60 MHz, d6-DMSO, delta): 7.4-7.6 (3H, aromatic ring H), 7.6-7.9 (2H, bs NH2).

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, 2,6-Dichlorobenzenesulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kureha Kagaku Kogyo K.K.; US6610853; (2003); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 14862-52-3, The chemical industry reduces the impact on the environment during synthesis 14862-52-3, name is 3,5-Dibromochlorobenzene, I believe this compound will play a more active role in future production and life.

A solution of 1,3-dibromo-5-chlorobenzene (10 mmol, 3.2 g)Diphenylamine (40 mmol, 6.7 g) was added to a 100 mL three-necked flask,A cuprous iodide (4 mmol, 0.8 g) was added under nitrogen,Potassium carbonate (40 mmol, 2.8 g),Phenanthroline (4 mmol, 0.8 g),50 mL of DMF,The reaction was carried out at 155 C for 3 days,The resulting reaction product is subjected to extraction,The extracted organic phase was evaporated to dryness with ethanol,And then recrystallized from ethyl acetate and petroleum ether to give 3.57 g of intermediate A-4,

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, 3,5-Dibromochlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jilin Aolai De Optoelectronic Materials Co., Ltd.; Gao, Chunji; Cui, Dunzhu; Sun, Yi; Zhang, Chengcheng; (52 pag.)CN104892434; (2017); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics