Category: 2729-34-2

Electric Literature of 2729-34-2, These common heterocyclic compound, 2729-34-2, name is 3,5-Dichloro-4-fluoroaniline, 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.

To a cooled (-20 C) solution of (R)-2-tert-butoxycarbonylamino-propionic acid (57.2 g, 302 mmol) in anhydrous THF (582 mL) was added JV-methyl-morpholine (34.9 mL, 317 mmol) at a rate to keep the internal temperature at -15 C. Isobutyl chloroformate (42.0 mL, 317 mmol) was then added over a 20 min period and the resulting mixture was stirred for 30 min. A solution of 3,5-dichloro-4-fluoro-phenylamine (54.4 g, 302 mmol) in THF (160 mL) was then added over 40 min. The reaction mixture was warmed to 20 C and stirred for 20 h. The reaction mixture was filtered and concentrated in vacuo. To the resulting oil was added MeOH (200 mL) and the solution was concentrated to provide the title compound as a tan colored solid, m/z 295.3 [M-?-Bu]+. This material was used without further purification.

Statistics shows that 3,5-Dichloro-4-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 2729-34-2.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/70485; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2729-34-2, 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. 2729-34-2 name is 3,5-Dichloro-4-fluoroaniline, 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.

To a suspension of ethyl 2-cyanoacetimidate hydrochloride (0.50 g, 3.36 mmol, Eq: 1.00) in ethanol (5.2 mL), was added 3,5-dichloro-4-fluoroaniline (606 mg, 3.36 mmol, Eq: 1.00). The suspension was stirred overnight at room temperature, under a nitrogen atmosphere. The reaction mixture was filtered to remove the salts. The clear yellow filtrate was then treated with hydrazine (in water) (313 mg, 310 mu, 3.42 mmol, Eq: 1.02) and heated in an oil bath at 80- 85C for 4.5 h. The reaction was cooled to room temperature and concentrated. The residue was partitioned between EtOAc and water. The organic phase was removed, washed with brine, dried (Na2S04) and concentrated over celite. The crude material was purified by flash chromatography (silica gel, SF 15-24 g, 20% to 100% EtOAc in hexanes) to give a light brown oil, which was further purified by HPLC (reverse phase, Sunfire Prep C18 OBD [5 uM; 30×100 mm], 5% to 95% acetonitrile in water (each containing 0.1% TFA)). The product-containing fractions were combined and freeze-dried. The freeze-dried material was taken up in EtOAc and washed with aqueous NaHC03 (lx) and water (2x). The organic phases was dried (Na2S04) and concentrated. The residue was dissolved in acetonitrile-water and freeze-dried to give 45 mg (5%) of desired product as an off-white solid. MS m/z 261, 263 [M+H]

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dichloro-4-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; PLANCHER, Jean-Marc; WEIKERT, Robert James; WO2014/135423; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2729-34-2,Some common heterocyclic compound, 2729-34-2, name is 3,5-Dichloro-4-fluoroaniline, molecular formula is C6H4Cl2FN, 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.

3,5-dichloro-4-fluoroaniline (1.0 g, 5.59 mmol) was dissolved in 10 ml HCl at 0C, NaN02 (386 mg, 5.59mmol) dissolved in water was added slowly and the solution was stirred at 0C until the solution was clear. The reaction mixture was slowly added a stirred solution of Potassium ethyl xantogenate (1.34 g, 8.38 mmol) in 15 ml water at 50C. The reaction mixture was stirred at 70C for 2 h followed by extraction with EtOAc (100 mL). The organic phase was washed by brine, dried over Na2S04, filtered and concentrated to give 1 g crude product which was immediately used in the next step.

The synthetic route of 2729-34-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALECTO BIOTECH AB; ZETTERBERG, Fredrik; LEFFLER, Hakon; NILSSON, Ulf; (131 pag.)WO2018/11093; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2729-34-2, name is 3,5-Dichloro-4-fluoroaniline, 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 2729-34-2, Product Details of 2729-34-2

3,5-dichloro-4-fluoroaniline (1534 mg, 8.5 mmol) dissolved in toluene (10 mL) was added to 4-chlorosulfonyl-1-methyl-pyrrole-2-carbonyl chloride (2063 mg, 8.52 mmol) in toluene (115mL) at reflux and refluxed 2 hours. The reaction mixture was filtered while still hot and thefiltrate was concentrated , yielding crude 5- [(3,5 -dichloro-4-fluorophenyl)carbamoyl] -1-methyl-pyrrole-3-sulfonyl chloride as a crude beige powder which was used as such.?H NMR (400MHz, acetonitrile-d3) oe ppm 3.96 (s, 3 H), 7.39 (d, J=2.0 Hz, 1 H), 7.71 – 7.77 (m, 3 H), 8.78 (br.s., 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dichloro-4-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2729-34-2, name is 3,5-Dichloro-4-fluoroaniline, 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: C6H4Cl2FN

(3,5-Dichloro-4-fluoro-phenyl)-[l-(4-methoxy-benzyl)-5-morpholin-4-yl-lH-[l,2,4]triazol-3- yl] -amine – In a 2-5 mL microwave vial, 4-(3-bromo-l-(4-methoxybenzyl)-lH-l,2,4-triazol-5-yl)morpholine (133.5 mg, 378 muiotaetaomicron, Eq: 1.00), 3,5-dichloro-4-fluoroaniline (81.6 mg, 454 muiotaetaomicron, Eq: 1.20), sodium tert-butoxide (109 mg, 1.13 mmol, Eq: 3.00), tris(dibenzylideneacetone)dipalladium (0) (20.8 mg, 22.7 muiotaetaomicron, Eq: 0.06) and di-tert-butyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (38.5 mg, 90.7 muiotaetaomicron, Eq: 0.24) were combined. The system was evacuated and recharged with nitrogen (2x). Toluene (1.08 ml) was then added. The mixture was stirred at room temperature for 5 minutes and then heated at 85C for 15 h. After cooling to room temperature, the reaction mixture was partitioned between EtOAc and water. The organic layer was removed, washed with brine, dried (Na2S04) and concentrated over celite. The crude material was purified by flash chromatography (silica gel, SF15-24 g, 20% to 100% EtOAc in hexanes) to gove 90 mg (53%) of desired product.

The synthetic route of 2729-34-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DING, Qingjie; JIANG, Nan; WEIKERT, Robert James; WO2014/135472; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 2729-34-2 as follows. 2729-34-2

General procedure: To a mixture of compound 19 (211 mg, 1.3 mmol, 1.0equiv) inethanol (10 mL) at 60 C, 18a (351 mg, 1.3 mmol, 1.0 equiv) wasadded. The reaction was stirred for 10 min, and then a warm sodiumbicarbonate solution (328 mg in 5mL water) was added over15 min. The reaction was stirred at 60 C for 1 h and then cooled toroom temperature. After extraction with ethyl acetate, the combinedorganic phase was dried over sodium sulfate and concentratedto give 20a as a crude brown solid (515 mg, 80%).

According to the analysis of related databases, 2729-34-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chen, Shulun; Guo, Wei; Liu, Xiaohua; Sun, Pu; Wang, Yi; Ding, Chunyong; Meng, Linghua; Zhang, Ao; European Journal of Medicinal Chemistry; vol. 179; (2019); p. 38 – 55;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2729-34-2, 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. 2729-34-2, name is 3,5-Dichloro-4-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 3,5-dichloro-4-fluoroaniline (1 g, 5.58 mmol) in con. HC1 (20 mL) was cooled to 0-5 C. A solution of sodium nitrite (424 mg, 6.14 mmol) in water (1 mL) was added dropwise over 20 min with stirring. The resulting solution was stirred for 1 h at 0-5 C. Potassium ethyl xantogenate (1.33 g, 8.37 mmol) was added and the reaction mixture was stirred at 70 C overnight. The resulting solution was extracted with EtOAc (20 mL x 3). The combined organic layers were washed with brine (20 mL), dried over Na2S04, and concentrated in vacuum to give crude product, which was purified by FC to afford crude product. The crude product dissolved in EtOH (20 mL) followed by addition of 2M NaOH(5.6 mL). The mixture was stirred at 70 C for 2h. The mixture was extracted with DCM(30 mL) and the water layer pH was adjusted to pH5-6 by NaHSCL aq. followed by addition of DCM (30 mL). The organic layer was isolated and was washed, dried over sodium sulphate and concentrated to dryness to give the title compound 90.2 mg which was used in the next step without further purification m/z calcd for [C6H3Cl2FS]+ [M-H] : 195.0; found: 195.0.

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; GALECTO BIOTECH AB; ZETTERBERG, Fredrik; (118 pag.)WO2019/137971; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics